Darviridis / Reflections

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hen I set off to write a book about the middle of bold projects and entrepreneurial journeys, you might expect that I started with my own. Having endured five years “bootstrapping” my own business and facing my fair share of challenges as an entrepreneur, this was my chance to share everything I learned. But I couldn’t remember anything. It wasn’t memory loss—it was just all a big blur. So I turned to the common source of answers to random ponderings these days: my phone. I flicked through years of random photos taken, back to the middle years of building Behance, my first company, hoping to jog my memory. I founded Behance in August 2006 and signed the documents to be acquired by Adobe in December 2012, so I made my way to 2009 on my phone, the absolute middle of my middle. Thousands of thumbnail images showed screenshots taken on my phone of website errors, bad copy, social media mentions of us and competitors, and various product ideas and changes. These screenshots spanned years and, in some months, outnumbered my photos. The sheer volume of them reminded me of falling asleep every night scrutinizing our product, anxiously looking for something but never knowing exactly what. I also found another type of screenshot—customer messages and feedback. I remember capturing these insights to share with my team, but also I needed them. I wanted to hold on to and extend some early semblance of reward and significance at a time when nobody seemed to care. Scrolling a little farther, I saw a reunion with college friends and then a special moment from my honeymoon during which my wife and I encountered elephants in Thailand. I was surprised to see how strained my smile looked. The memory rushed back, and I recalled the tension of wanting to relish this once-in-a-lifetime moment while realizing I had a team at home running on fumes and I was just a few months away from missing payroll. Being away from the team felt utterly irresponsible, and this burden followed me everywhere. Scrolling farther now, I stumbled on a team event at a restaurant kitchen where we all cooked a meal together—we couldn’t afford it, but I knew the only thing that mattered was keeping the team together. As I scrolled through our team pics, I was struck by how close and dedicated we became despite the circumstances and our differences. When the odds are against you, without revenue or margin to protect you, teams and relationships are different. It’s not work; it’s survival and self-discovery. These photos reminded me just how exhausted and uncertain I had been —fueled by my relentless determination to make something awesome. Perhaps, in such periods of struggle, our preoccupations and emotions take up so much mind share that the events themselves become a blur? Or perhaps we don’t remember the middle because we don’t want to? • • • ou’re probably reading this book because you’re about to embark on a massive journey—or are already trekking through the middle of one. Whether you’re a writer, start-up entrepreneur, big-company innovator, or an artist, you share many of the same hopes and fears. You might be working within a multinational company, a small nonprofit, a new creative studio, or on your own. No matter what it is you’re trying to create or transform, the myth of a successful journey is that it starts with the excitement of an idea, followed by a ton of hardship, and then a gradual and linear rise to the finish line. But no extraordinary journey is linear. The notion of having a bold idea and making consistent incremental progress is impossible. Those seeking a linear journey with less instability can still be successful, but they often struggle to create anything new. In reality, the middle is extraordinarily volatile—a continual sequence of ups and downs, expansions and contractions. Once the honeymoon period of starting a new journey dissipates, reality hits you. Hard. You feel lost and then you find a new direction; you make progress and then you stumble. Every advance reveals a new shortcoming. Major upsets give rise to new realizations that lead to breakthroughs in progress. At best, you move two steps forward, one step back—at worst, you realize you’ve been walking the wrong path entirely for months. This is what that journey actually looks like. I’ve come to call the journey of creation one of “relative joy.” Your job is to endure the lows and optimize the highs in order to achieve a positive slope within the jaggedness of real life—where, on average, every low is less low than the one before it, and every subsequent high is a little higher. In the moment, you can see only the uphill or downhill in front of your nose, but over time, you come to recognize that there is a median that keeps you moving forward in the right direction. The volatility of this tug-of-war is hard to stomach. You must pay less attention to the day-to-day incremental advances and more on achieving an overall positive slope. And that’s entirely determined by how you navigate the messy middle.

IT’S NOT ABOUT THE START AND FINISH, IT’S ABOUT THE JOURNEY IN BETWEEN.

here are just a handful of thrilling and treacherous moments as an entrepreneur. Most of them happen at the start or finish of the journey (or one of the restarts or false finishes along the way). They’re all we talk about, but they reveal very little about the journey itself. We love talking about the starts. The start is romantic. We love talking about it because it is inspiring without the complication of substance and strife. Conception is an adrenaline rush fueled by grandiose visions paired with naivety. You’re inspired by a destination and have no idea how you’ll get there. The solution in your mind’s eye is rose colored. You don’t yet know how the cards are stacked against you. In this case, ignorance is not only bliss but also enables you to dream up solutions at the edge of reason. You’re untethered. We also love talking about finishes. We imagine the rush, the exhaustion, and the pride of finally making it. This is what we dream of throughout the struggle of creating, isn’t it? How relieved we’ll be when the workout is finally over. A “finish” can happen at different parts of a journey: Launching a product. Publishing a book. Raising money. Reaching a key milestone. Being acquired. Shutting down. Going public. Closing the quarter. The press likes to write these headlines and we like to read them. But the superlatives obscure the fact that they are simply abstract mile markers. We learn very little from these moments despite their gravity. One of the strangest parts of being an entrepreneur is being part of a community obsessed with starts and finishes. Investors tend to be interested only in starts (when they’re able to invest) and finishes (when they get a return). Similarly, stories tend to be written only about public inflections. Even between entrepreneurs or big company CEOs, what is intended as a network of support becomes an echo chamber. Nobody wants to talk about their self-doubts and the insecurities that fuel them. Every business is “going great” until it fails. The bumps along the road are endured in isolation. The majority of the journey itself is unchronicled because it is unappealing and too revealing. As a young entrepreneur, the focus on starts and finishes always bothered me. As a manager, I sought to hire people who were seeking a journey rather than a particular outcome. The more immersed I became in the start-up world, the more I wanted to operate without sensationalism.

T When the journey feels gritty and real, your potential becomes more tangible. Then I went to work as an investor with dozens of entrepreneurs at all different stages of company building, where it became clear how destructive the spotlight on starts and finishes really is. As we celebrate the success of others, we’re liable to draw lessons from a drastically edited story that excludes the middle. What’s in the middle? Nothing headline- worthy yet everything important. Your war with self-doubt, a roller coaster of incremental successes and failures, bouts of the mundane, and sheer anonymity. The middle is seldom recounted and all blends together in a blur of exhaustion. We’re left with shallow versions of the truth, edited for egos and sound bites. Success is misattributed to the moments we wish to remember rather than those we choose to forget. Worst of all, when everyone else around us perpetuates the myth of a straightforward progression from start to finish, we come to expect that our journey is meant to look the same. We’re left with the misconception that a successful journey is logical. But it never is. Don’t let others’ stories pervert your understanding of the journey. Emulating someone else’s story is following a playbook without all the pages in the middle. We don’t talk about the messy middle because we’re not proud of the turbulence of our own making and the actions we took out of despair. Sharing our challenges shakes our egos. And finally, the middle of a journey doesn’t make for good headlines. The middle isn’t pretty, but it is illuminating and full of essential realizations to finish whatever it is you set out to start. It’s time we start talking about it. • • • he journey to create a product or service is reflected in the outcome in ways you may not even expect. It matters, tremendously. Consider a product you use in your everyday life—is it simple or complicated? Too many features or just the functionality you need? Is it enjoyable or is it a chore? The experience of using someone else’s creation comes from the path the creator took to make it. It is not the plastic, metal,or pixels that make a successful product or service. Rather, it is the thoughtfulness and tough choices made by the makers—the team dynamic, the perseverance, the organizational design (and redesigns), the constraints, the battles fought, and the values that governed the path taken. This book is about mining every insight from the volatility and the depths of despair to improve your team, product, and self. This book is also intended to help you survive the creative process when you lack any sense of traction, recognition, or significance. A few years ago I set out to understand what founders and other leaders of bold new projects do throughout their journeys that they don’t talk about. I sought to chronicle the pain-management techniques, the tactics for optimizing, and the instincts that not only help their teams survive the journey from start to finish but also thrive. This book is the culmination of seven years’ worth of scribbled notes, mobile memos captured on the run, and one-liners committed to memory. It covers insights witnessed and realized in boardrooms, on midnight calls with teams solving a crisis, during sleepless nights fretting difficult decisions, in brainstorming sessions with entrepreneurs, and often in the reflective haze of long-haul plane flights. The perspectives in this book are derived from experiences with many different people and teams, from entrepreneurs to writers from small agencies and start-ups to billion-dollar companies transforming their industries. When a tactic or tenet fascinated me, I’d capture it and share it with others for feedback or better ideas, and the ones that made the cut are in this book. The following pages cover insights garnered from interviews, from my own struggles and relative triumphs, and from working alongside the many entrepreneurs I have advised over the years. While the insights are organized into sections, the book is intended to be more of a buffet than a plated six-course meal. I encourage you to navigate to whatever parts of the journey resonate most at the moment, using the table of contents. As they have for me, I hope these insights bolster your confidence, fortify your plans, and make you question your assumptions. As you seek to make an impact in what matters most to you, this book will help illuminate your path from start to finish.

I THE STORIES FALL SHORT. n 2006, I founded Behance, a company devoted to connecting and empowering creative professionals. The problem my team and I set out to solve was a simple one: The creative world was one of the most disorganized communities on the planet—there was no way to track a photographer’s work, find out who designed a particular product, or track down the motion graphics artist or creative director behind a particular campaign. We wanted to help organize creative people, teams, and the community at large. The problem was simple, but the solution was anything but. After several fits and starts, lessons learned the hard way, and five years of bootstrapping (building a business that relied on revenue rather than venture capital), we built a multifaceted business. The Behance Network grew to enable more than twelve million creative professionals to showcase their work, connect and collaborate with one another, and get jobs. Over the years, Behance became the leading online platform for creative careers and provided me with the opportunity to grow a large design and technology team. We then expanded Behance by offering content and events for the creative community, online and off-, by creating a think tank, website, and annual conference called 99U in 2007. Influenced by the famous Thomas Edison quote, “Genius is 1 percent inspiration and 99 percent perspiration,” 99U is dedicated to the execution of ideas rather than the ideas themselves. In late 2012, Behance was acquired by Adobe, one of the world’s largest technology companies responsible for products like Photoshop, Illustrator, and the PDF (Portable Document Format), among many other products for the creative world. It was an incredible and unexpected outcome for the entire team—certainly not the one I imagined for myself when I started designing paper products and running seminars for freelance designers to pay the bills. I joined Adobe as a vice president of products, leading an overhaul of the company’s mobile and cloud asset strategies. The three years that followed were enlightening in ways I didn’t expect. I had to wind down old products, help launch new ones, and lead teams through a great deal of uncertainty and change. I left this role with an appreciation for the frictions in a big company—how they hurt, how they help, and how to keep the ship moving forward, inch by inch. Being an entrepreneur working at the intersection of design and technology brought all sorts of opportunities as an investor and adviser to help fellow entrepreneurs build their teams, brands, and products. Some of these companies, like Pinterest, Uber, Warby Parker, sweetgreen, and Periscope, are now successful operations that have, at least to some degree, accomplished what they set out to do. Others are still meandering mid- journey, enduring their rough patches and optimizing on the upswings in every way they can. But regardless of the stage, change is the only constant. After successfully seeing my own business over the finish line, and three years at Adobe, I spent a couple of years as a full-time investor, adviser, and occasional cofounder, working shoulder to shoulder with entrepreneurs and helping them navigate their own journeys. And then, at the end of 2017, I jumped back into the fray, building products and services for creative people as Adobe’s chief product officer. When sharing my story of Behance, I normally skip over the years of challenge and personal growth that existed in between the start and finish. The story I normally tell goes something like this: We bootstrapped the business for five years before one of our products, the Behance Network, eventually started to gain traction. This allowed us to raise some funding from a top-tier VC [venture capitalist] firm, which gave us the chance to build a dream team that turned our product into a ubiquitous global creative platform. When Adobe turned Photoshop and the rest of their software into a subscription service, they needed a network like ours. The timing and opportunity was great, so Adobe acquired us. It was a great outcome for the entire team, and we happily continued working together for years afterward. And boom, an entire decade of work tied with a bow. My tale sounds a lot like other pithy stories of humble beginnings, progress, and an ultimately successful outcome. But there were years at Behance when nobody beyond our team seemed to understand or care about our work. There were moments when it all seemed on the brink of falling apart. In fact, in the early days, antinausea medication was my only way to keep an appetite. Everyone doubted us—if they ever cared—and I endured bouts of self-doubt as well. Persevering long enough to transform vision into reality was harder than I ever thought it would be; anything that challenged the status quo was an uphill battle, and the natural forces of rejection that kill new ideas didn’t discriminate between the good and the bad. Innovation has a nasty headwind, rarely a tailwind. In our first year it was just four of us. We were completely unqualified for the journey ahead, but our lack of experience didn’t shake our confidence and determination, which came from our love of an idea—and the sheer ignorance for what would be required to make it happen. Matias Corea had recently arrived in New York City from Barcelona and had practiced graphic design only for a few years. When we first met, he showed me a small brochure he had designed for a saxophone manufacturer. Matias loved jazz and typography, but he had never designed a website. Dave Stein joined us straight out of college. He had studied psychology and had covered his tuition by building simple websites out of his dorm room. The showcase website on his résumé was for an erotic lingerie shop in upstate New York. Our third hire, Chris Henry, had built a few websites in the year or two since he’d graduated from college, but he had never built search applications or databases. And me? My day job was working as an associate at Goldman Sachs. I had taken some design classes in college, but I was not an engineer, and I had never led a company. I had meandered through the worlds of finance and organizational development, but my real aspiration was to create digital products and work in the creative industry. I had assembled this team of newbies to explore an idea that would connect the creative industry. The odds were most certainly against us. We didn’t know it yet, but we were embarking on a decade-long journey that would shape both us and the global creative community in unimaginable ways. So let’s get real: The pithy success stories we hear are missing something. My short story of Behance is equally puzzling. How does a team stay together for five years with no traction, barely making payroll? How do you stomach years of anonymity and blank stares when you tell others what you’re doing? How does an unqualified team recruit, manage, and retain very qualified people—often more qualified than ourselves? How do you survive long enough in an industry you know nothing about to become an expert? How do you keep changing (and often killing) parts of your business without destroying morale? And how does a team with no experience pull off something like this? The volatile terrain of the messy middle of a journey is the real story nobody talks about. Left to hack the middle of the journey on our own, we quietly endure the downs and optimize the ups as best we can. We experiment with ways to motivate our teams when problems feel insurmountable. We agonize over conflict and try to manage drama. We act as magicians, helping our coworkers feel incremental progress when there is none. The dirty little secret that entrepreneurs hate to admit is just how fine the line is between their success and failure. The middle makes and breaks you, and ending up on the right side of this line depends on how you manage everything in between. It requires immense perseverance, self- awareness, craftsmanship, and strategy. It also requires luck, harvested whenever you encounter it. As we struggle, we gain insights. Hardship forces us to optimize. Our instincts are honed and our intuitions sharpen. These gems from the journey make you more capable for whatever comes next, and in my own life, they have made all the difference.

START, ENDURE, OPTIMIZE, FINISH, THEN REPEAT. The Start The start is pure joy because you’re unaware of what you don’t know and the painful obstacles ahead. Wearing the start-up world’s equivalent of beer goggles is important at the start, because very few would ever have the tenacity to begin their journey otherwise. But after the excitement of a new idea dissipates, reality sets in. You’ll become mired in logistics and daunted by the unknown. You’ll frantically attempt to level out your overworked synapses. You’ll be in a freefall without knowing how far away the bottom is—and that’s when the headwinds kick in. Everyone will doubt you. You will struggle to see your own progress. You’ll realize that your industry, your team, and your competitors don’t like change—and society doesn’t, either. Not even your customers. And then finally: The bottom arrives, and you hit hard. After scrambling to get your bearings and not lose too much time, money, or face, you’ll look back up to see a monstrous peak in front of you. This is where the journey truly begins. The Middle: Enduring and Optimizing The middle of the journey is all about enduring the valleys and optimizing the peaks. After the joy of conception subsides, your objective is to make every setback less difficult than the one before it—and make every recovery hoist you slightly higher than where you were before. To achieve the elusive positive slope, you must endure the downs (the incremental setbacks and struggles) and optimize the ups (everything and anything that seems to be working). Your progress will feel rewarding, but only relative to your most recent struggle. The best you can do is harvest and integrate the insights you need to keep moving in the right direction up the slope. Volatility is good for velocity. The faster you move and the more mistakes you make, the better your chances of learning and gaining the momentum you need to soar above competitors. Moving fast means conducting lots of experiments—many of which will fail—and making quick turns that are liable to leave you and your team dizzy. This volatility can hurt morale and cause anxiety, but you have a better chance of extraordinary results. The middle of the journey is an excruciating struggle. But there are momentary recoveries throughout the journey that keep you going, like the sensation of seeing your team’s DNA in your product, meeting a customer who sincerely thanks you, watching a culture take shape and the people you hired evolve to become entirely different leaders . . . there are so many moments along the way that keep you going. You just need to endure the lows and optimize everything that works. The Finish Your “finish” is the final mile of your journey and the recovery time between one project and the next. It’s hard to know when you’re finished, because every project has a piece of you in it that never goes away. In this way, the finish is more a state of mind. However, there are inflections in every project where everything changes: You debut your creation to the world, you sell your company, or you publish your book. Even though the race continues, it feels like a finish because you’re no longer racing against the clock. Either the volatility P subsides or your interest ceases—or both. Your pace changes, and you finally allow yourself to take a break and make a change. Finishes come in all shapes and sizes and are never as certain (or desirable) as they seem. In fact, finishing should never be the end goal, and you shouldn’t aspire to ever feel truly “finished”; life loses value when challenge dissipates. In my own experience at Behance, our founding team didn’t have a particular finish in mind when we started. Sure, I imagined a day in the distant future when we might be profitable, have an amazing team, make a profound impact, and be running a brand and company we were proud of. But getting acquired was not even a subconscious thought within that early narrative. In the end, Behance’s acquisition provided a natural punctuation mark for the end of a chapter. Journeys have all kinds of finishes along the way, and in many respects, you’re never finished. You can always write another chapter. • • • Part of my motivation to write this book was to “out” a bold creative project or new venture for what it really is: endless endurance and optimization. I have organized the insights ahead into a section on endurance and a section on optimization—the two complementary forces that help you conquer the middle of any bold project. Fair warning, the “Endure” section will be uncomfortable and, at times, frustrating to read. Rather than sugarcoat the hurt, anguish, and doubt, I have worked to bring these emotions and painful moments to the forefront. It’s important to become familiar with these inevitable hardships and how others worked through them. When you make your way through “Endure,” you’ll be greeted by a more optimistic and actionable “Optimize” section that is all about capitalizing on your strengths and improving every aspect of your team, product, and self. Enduring and optimizing is the rhythm of making—the pattern of ups and downs that every journey takes you through. It is certainly true for your professional aspirations, but this rhythm also applies to all of life. One realization I hope you have from this book is the relationship between volatility and preparedness. The lengthy distance between where you are and where you wish to be—with all of its difficulties—is there for a reason, and the ups and downs feed each other in valuable ways. In Zen, the Buddha says you cannot travel the path until you have become the path yourself. Only by embracing the middle will you find your way through. The easiest route to take is to glide in the direction of wherever fate pushes. But living at the mercy of circumstance makes you a passive participant in your own story. Without a fight against fate (aka the status quo), you’ll never venture beyond the expected. You can stretch your potential only by enduring the volatility of the journey, by getting curious about the bumps, and by optimizing every aspect of your product, team, and self.

T ENDURE hree years in. Or maybe it was two, or four. I have no idea. The middle years all blend together. I call them the “lost years,” because Behance’s progress felt excruciatingly slow, and we learned everything the hard way. I’m surprised we survived. Our team was our own little world. We manufactured our goals and self-esteem in the same way we made our product: with imagination and poetic license. The fights and fun were all part of the drama that kept our made-up world intact. We barely had a business, and most of our customers were doing us a favor. Our relationships with one another and our sense of hope were the only things we were building with undeniable value. Nevertheless, I felt so small whenever I walked out of our office, which was a cordoned-off part of my apartment a few blocks away from Union Square. New York City was always bustling. The guy selling fruit on the sidewalk had more customers than we did. Out at night I cringed when the “what do you do?” conversation came up. I knew my answer—building a company to help organize the creative world—would get a blank stare. Would people think I got fired from my real job? If I told people my vision, would I lose respect if I failed? My family and friends always offered to help me, but there was nothing they could do. I felt the weight of every decision, and the careers of those who quit their jobs to join me, on my shoulders. My shoulders alone. When I think back to those lost years, I recall a constant somber loneliness, a suffering from the feeling that nobody else could relate. The struggle was further compounded by the optimism I had to exude to my team and potential customers and partners. My hope had to be mined deep beneath the surface of fear and reality. The juxtaposition of the intensity of a start-up and feeling invisible and despondent was soul crushing. Staying positive was exhausting, and there were times when I felt depressed. Aside from the psychological struggles, these years felt lost because we ran in circles. We had to rebuild the Behance Network’s core technology three times. We switched vendors, hired some of the wrong people, and made countless bad decisions. Keeping our product functional was a game of Whac-A-Mole: Every fix seemed to break something else. But we were determined to get it right. We didn’t make rapid progress with our product, but the hardship strengthened our resolve. As a team, and as individuals, we found a way to endure every valley we faced. The middle miles of a venture are full of ambiguity, uncertainty, fear, runarounds, crises, disagreements, and endless bouts of the mundane. Every time you untangle yourself and find your way out of a jam, you’ll fall into another one sooner than you think. These are the inevitable and seemingly endless dips of the middle that we must endure. Endurance is about much more than surviving late nights and laboring without reward. It’s about developing a source of renewable energy and tolerance that is not innate. Without any customers or evidence of progress, the continuous validation and encouragement that motivates teams will be absent. Without a steady stream of rewards, you will feel empty. You must supplement this void with manufactured optimism. You will have to endure anonymity and a persistent state of frustration. You’ll have to generate a unique and intrinsic sense of belief in yourself as you manage the blows to your plan and ego. Sure, your passion for the problem you’re solving will help. But running a marathon while hungry requires supernatural sustenance in the form of some key insights and convictions that we will discuss in this section. The line between a big win and failure is thin. You can get the important stuff right and still lose by not enduring long enough. When I recall our years of bootstrapping at Behance, I cringe thinking about just how close we came to falling apart—several times. We survived these troughs in our journey as a team. We relied on one another, managed to find levity in even the darkest moments, and hacked our own reality to endure years of struggle. The insights in the section ahead will equip you for the middle- journey turbulence. They will also remind you that you’re not alone. But we need to face the mess head-on and learn how to endure and mine the volatility. Exploring the trenches of lost hope, uncertainty, and exhaustion help make such conditions more familiar—and therefore bearable, maybe even manageable. LEADING THROUGH THE ANGUISH AND THE UNKNOWN

Short-circuit your reward system. One of the greatest motivators is a sign of progress. Hardship is easier to tolerate when your work is being recognized (either through external validation or financial rewards), but long journeys don’t show progress in the traditional sense. When you have no customers, no audience, and nobody knows or cares to know about what you’re making, the greatest motivators have to be manufactured. I would characterize much of my first few years leading my team at Behance as an adventure in manufacturing motivation. In 2007, and for a few years thereafter, we had very little traction, revenue, press, or any other traditional form of progress to celebrate. We had launched a blog and simple network for creative professionals . . . that nobody knew about or cared about. When you did a web search for Behance, the first result was Did you mean: enhance? Even Google thought we were a mistake. The traditional measures of an internet business—page views, customers, subscribers, revenue—didn’t do much for us because we were starting from nothing and struggling to exist. As the team’s leader, I tried all sorts of ways to keep the team engaged. We would make bets for when we would achieve certain milestones based on our priorities. As a lifelong vegetarian, I would commit to trying certain kinds of meat if we reached certain milestones (which the team found, strangely, motivating). We would celebrate any new customers, even if the overall numbers were tiny. We would celebrate completing a page of tasks on the wall or bashing a particularly elusive bug in the software with cheap champagne. Whatever we could repurpose as a milestone, we would. One of my favorite early manufactured milestones was overcoming Google’s Behance/enhance error message. We longed to be considered a legitimate search result. To achieve this, we needed to game the spread of “back links” to influence Google’s search algorithm. We knew that the more blog posts we wrote and the more portfolios our customers uploaded, the closer we would get to internet recognition, not by our customers, but by Google’s digital gatekeepers. The goal was short term, and the tasks to achieve it were all actionable. It would just take time and effort. “Someday,” I assured the team, “we will no longer be a mistake.” Then one day, someone on the team went to Google and gave it another go and, lo and behold, Behance came up as the first result without any prompt to correct the search query. We had won—we finally existed! It was a small win manufactured as a way to help us feel a semblance of progress, but it felt great. And then, I kid you not, in 2008, Beyoncé became popular. And we were a mistake again. Did you mean: Beyoncé? Google asked. But we were undeterred, and it was only a matter of weeks until we were, once again, a legitimate search result. It is hard to summon a sense of hope and self-worth when you’re on your own. So you squeeze out any semblance of progress you can find, and then you celebrate it. The great void of feedback and reward that early-stage start-ups must endure cannot be overstated. It is especially apparent when I attend start-up conferences like Web Summit, an annual gathering of start-ups from Europe, the Middle East, and Asia. While the United States has an established ecosystem of start-ups, incubators, venture capital firms, and angel investors, the rest of the world benefits from megaconferences like Web Summit to bring entrepreneurs and investors together. Strolling around the start-up pavilion at Web Summit, I always take heart in the literally thousands of start-ups that have a three-foot-long space to engage anyone willing to hear their pitch. It’s fun to see so many ideas in the early stages, but with all the energy I also feel the pain and despair. When you’re putting everything on the line, your business and art becomes intertwined with your identity and self- esteem. Nothing is more humbling than everyone passing by your three-foot cube that represents your future without even taking a second look. Anonymity means you can make mistakes and drastic changes to your product without disappointing anyone, but only because nobody cares. Breaking through anonymity is a game of endurance, so you have to hack your reward system so that the absent short-term rewards you typically rely on, like revenue or new customer goals, are replaced by something else. Starting at a very young age, we are trained to be governed by a powerful short-term reward system. As toddlers, we behave in ways that yield affection and instant gratification from our parents. In school, our learning is rewarded with good grades. And grades, we soon learn, yield the reward of approval from parents, teachers, and peers. When we enter the job market, we receive a monthly salary and bonuses. And as legendary venture capitalist (VC) Fred Wilson paraphrased at the 99U conference: “The two greatest addictions in life are heroin and a weekly salary.” Monica Mehta, author of The Entrepreneurial Instinct, studies the role of brain chemistry in entrepreneurship. She explains in Entrepreneur, “With each success, our brain releases a chemical called dopamine. When dopamine flows into the brain’s reward pathway (the part responsible for pleasure, learning and motivation), we not only feel greater concentration but are inspired to re-experience the activity that caused the chemical release in the first place.” This guaranteed dopamine rush and the self- confidence it provides makes short-term rewards addicting. Alternatively, “Each time we fail, the brain is drained of dopamine, making it not only hard to concentrate but also difficult to learn from what went wrong.” Thus, physiologically, we’re hardwired to have a strong preference for actions, decisions, and projects likely to yield quick wins, because delayed gratification causes anxiety and discomfort. If you consider how short life expectancy was in the dawn of humanity, it’s no surprise that we’re naturally biased toward short-term rewards. Even as late as the seventeenth century, average life expectancy in New England was twenty-five years of age, and 40 percent of people died before reaching adulthood. For early humanity, the prospect of spending five or ten years working toward an eventual outcome, however great it might be, was just not rational. No wonder it is so difficult to stay engaged with a long-term goal—we are biologically wired to abandon such efforts in exchange for shorter-term rewards. Our addiction to short-term validation is so engrained that trying to defy it is hopeless. Accept this fact. While many people paint an incredible long-term vision for their teams, the prospect of long-term rewards is insufficient for long-term motivation. It is virtuous to aspire to these goals, but a noble venture is not exempt from the need to feel incremental progress and be rewarded for it. Rather than fight the need for short-term rewards, you must hack your reward system to provide them. As you craft your team’s culture, lower the bar for how you define a “win.” Celebrate anything you can, from gaining a new customer to solving a particularly vexing problem. The problem with traditional rewards like money, which can be counted and accumulated, is that they require the least imagination. Make the most of the period in your journey when you must create your own rewards out of necessity. By doing so, you are engaging your team more dynamically than a raise or bonus ever will. Milestones that are directly correlated with progress are more effective motivators than anything else.

Don’t seek positive feedback or celebrate fake wins at the expense of hard truths. While important to celebrate and manufacture wins early on, make sure they’re not fake wins. It’s understandable to seek validation, but actively searching for positive feedback provides false positives. If you keep searching for something positive, you’ll find it—but often at the expense of more important truths. In the early days of founding Behance and helping start other companies like Prefer, a referral network for independent professionals, I found myself looking at our product analytics every day. Did more people sign up today than yesterday? Did engagement go up this week versus last week? How many more followers did we gain on Twitter? These are important metrics to track, but I was looking only for the positive trends rather than objectively reviewing all the trends. More than anything else, I wanted validation. Upon reflection from several start-up experiences, product manager and technology entrepreneur Ben Erez talked about the perils of being encouraged by positive feedback. When you’re starting a company, anything resembling positive feedback looks like a delicious steak. I’ve never enjoyed hearing how awesome my idea was than I did during the process of starting my company. I’ve never had a baby, but to me having a start-up felt a lot like showing off my new baby. You tell everyone about it like an excited parent and every single person congratulates you for the news and tells you it’s flawless. In hindsight, seeking positive feedback was toxic, because it was giving us the impression we were on the right track. To objectively observe the performance of your new creation or product, put yourself in others’ shoes. You can piece together something resembling the truth only from many different perspectives. How would a skeptical investor look at your numbers? How would an impatient new customer attempt to navigate your product? What are competitors saying about your product? Actively seek out the negative trends as well as the positive, as your longevity over time will be determined by your awareness of weaknesses as much as your strengths. It’s all too tempting to sugarcoat a bitter pill. Momentum is an especially effective distractor, as are press accolades. But finding a positive metric or getting glowing press coverage does not make a hard truth go away. Our thirst for good news means we focus on it, or worse, manufacture it. Sometimes when leaders are trying to rally confidence and support, they are actually blunting a blow that must be felt in order to feel the reality and make difficult decisions. I often see leaders circulate positive articles to their teams to overshadow larger problems facing the company. As an investor, I see this in shareholder updates from entrepreneurs running businesses I’ve supported. These updates almost always start with “Things are going really well!!” and then, buried on page 5 of the update, is the news that the team has been pared down to two people, they’ve had to move out of their coworking space, and they have five months of funding left before they stop paying salaries. “But Forbes gave us a great write-up last month!” It’s the business equivalent of the grimacing emoji. As Ben Horowitz, founder and general partner of venture capital firm Andreessen Horowitz, once explained in a blog on the topic, “The truth about telling the truth is that it does not come easy for anyone. It’s not natural or organic. The natural thing to do is tell people what they want to hear. That’s what makes everybody feel good . . . at least for the moment. Telling the truth, on the other hand, is hard work and requires skill.” He goes on to cite the kinds of messages that are painful to deliver, like executives quitting, a plan for massive layoffs, sales declining, and other perilous situations. “You must tell the truth without destroying the company. To do this, you must accept that you cannot change the truth. You cannot change it, but you can assign meaning to it.” Ben suggests three methods for assigning meaning to hard truths: State the facts clearly and honestly—Don’t try to say that you needed to clean up performance issues or that the company is better off without the people that you so painstakingly hired. It is what it is and it’s important that everyone knows you know that. If you caused it, explain how such a bad thing could occur— What was the decision process that you used to expand the company faster than you should have? What did you learn that will prevent it from happening again? Explain why taking the action is essential to the larger mission and how important that mission is—A layoff, if done properly, is a new lease on life for the company and an action that was necessary to fulfill the prime directive and mission that everyone signed up for. As the leader, it’s your job to make sure that the company does not let those people lose their jobs for nothing. Something good needs to come out of it. Despite the temptation, don’t focus on “good news” at the expense of what’s going south and how to deliver bad news. In a journey that is so reliant on positive energy and hope, it is vitally important to make consistent time and space where people can focus on what isn’t working. Perhaps it is a regularly scheduled monthly meeting, or a period during an off-site meeting when the team is encouraged to share their doubts. Some teams do anonymous surveys of the team’s gravest concerns and then share the results. Whatever your method, don’t gloss over the news your team needs to hear. Be up front, and then share a plan. You cannot win unless you know how you’re most likely to lose. And when you find something worth celebrating, only applaud the progress and actions you want your team to repeat. It’s dangerous to celebrate accolades or circumstances that are not linked with productivity, like getting “press” that you paid for or winning awards that are not representative of your impact. After all, the most exciting pursuits don’t yet fit in a reporter’s beat or an award category! Another example of a dangerous fake win is raising capital. Funding shouldn’t be celebrated. If anything, raising money should make you nervous: It means you have more to lose and more people you are responsible to. For strong companies, financing is a tactic. For weak companies, financing is a goal. When you use smoke and mirrors to help boost self-esteem and help your team endure hardship, you’re perverting your values. Fake wins are the reward equivalent of cocaine: They will artificially inflate morale but then take you down, perhaps lower than where you started. What should you celebrate? Progress and impact. As your team takes action and works their way down the list of things to do, it is often hard for them to feel the granularity of their progress and you need to compensate. Celebrate the moments when aggressive deadlines are met or beaten. Pop champagne when the work you’ve done makes a real impact. Even if it’s just a few customers that make use of a new product or feature, these are the real milestones you want to celebrate.

Accept the burden of processing uncertainty. We crave certainty but must learn to function without it. We want to be told that a glass of wine a day is definitely good for us, but life isn’t that simple. While searching for a definitive answer, we often cherry-pick insights from experts or studies that support the view we already hold. By avoiding uncertainty and desperately seeking a quick answer, we’re liable to embrace premature or incorrect solutions. Only by learning to tolerate uncertainty can we allow processes to play out and experiments to unfold. Emre Soyer, a behavioral scientist and assistant professor of business at Ozyegin University in Istanbul, Turkey, has studied leaders navigating uncertainty and decision making: “A leader that embraces uncertainty would be open to experiment with different ideas and let others experiment, too, rather than claiming to know the correct answer all the time.” When searching for stability, we’ll often cut corners or ignore real issues in order to stem our fear of the unknown. “We often desire that experts absorb uncertainties for us, make consistently accurate predictions and tell us what we need to do,” Soyer says. “Yet this would lead to a false sense of certainty and an illusion of control, ultimately causing us to invest in some particular strategies or treatments that may prove useless or even harmful.” Instead, we should train our brains to embrace the gray area and not be too solution driven. “One of the main responsibilities of a leader or an executive is to make good decisions,” Soyer adds. “Yet, uncertainty makes this task difficult. Claiming an unwarranted degree of control on uncertain situations can harm the reputation of the leader in the long run. Whereas a leader who is behaving in harmony with the uncertain nature of a situation would be judged as fair and competent even if sometimes the outcomes are unsatisfactory due to bad luck.” The necessary but difficult task of embracing the gray area means willingly wrestling with uncertainty on a daily basis. I struggled with this in my early years spent bootstrapping Behance, with no end in sight and no sure sense of traction. I remember many occasions when I valiantly fought to disconnect: Christmas, the week of my wedding, and even the birth of my daughter. And while I was “there” for all of these moments, 20 percent of my mind’s processing power was preoccupied. It wasn’t any specific deal or issue that stuck with me. On the contrary, it was the stuff I didn’t know that ate away at me—the “unknown unknowns.” The lack of a map for the voyage ahead caused an existential angst that meant I felt the need to live and sleep with one eye on the compass. As Ben Erez recalls from his experience, “I thought at the time that my personal life was separate from my work life, but that’s not true in entrepreneurship. When you’re building a company, the various parts of your life have a way of all meshing together into a think blend that doesn’t let you tell one part from the other. I had heard starting a company is all- consuming but the magnitude of overlap was something I was not prepared to handle.” This “think blend” is the continual processing of open questions without absolute solutions. In many ways, the continual processing of uncertainty is the one part of your “work life” you can’t turn off. There’s no shortcut to deep thinking and crunching through scenarios in the basement of your brain. So you must practice and learn to master the art of parallel processing, when you can focus on a specific problem while also churning through the omnipresent anxiety. You can quiet it down, but you can’t turn it off (and you don’t want to—you’re slow cooking your intuition). Some people I know practice meditation, and some pride themselves on being able to ruthlessly compartmentalize. What I try to do is remind myself that I need to be present with my team, focused on the problem, yet keep a pulse on the big picture. Despite what may be processing in the back of your mind, try to get curious with whatever problem or person is in front of you. Distract yourself from your own preoccupations by finding things to learn and solve. No matter what your creative endeavor is, uncertainty will be lingering around every corner. There is simply no way around uncertainty and the angst it will cause for you and your team. Strive to continually process it rather than let it cripple you, to accept the burden without surrendering your attention.

Fight resistance with a commitment to suffering. Society has a grand immune system designed to suppress new ideas. To keep the water running and sustain life’s other necessities, society’s natural resistance to ingenuity surfaces in the form of doubt, cynicism, and pressure to conform. It takes tremendous endurance to survive such resistance. In order to fight against the resistance, you’ll need more than passion and empathy. You’ll need to commit to suffering for the years required to push your idea to fruition. Not just a willingness to suffer, but a commitment. Loup Ventures investor Doug Clinton makes the case that founders must commit to suffering for at least five years. “This might sound more extreme than necessary,” he writes, “but starting a company is a roller coaster of suffering. You need to be comfortable with hearing ‘no’ over and over and not let that destroy your will. You need to be able to withstand low periods that are inevitable—unexpected customer or employee losses, investor rejections, tax bills, fights with cofounders. Entrepreneurs don’t necessarily need to revel in difficulty, but it helps. . . . It usually takes at least two years before you have any reasonable traction to show that your business might be working, then another few years of driving growth to create something that looks like a moat. Then you can afford to breathe. A little.” With a commitment to suffering, teams are able to tolerate struggle and overcome major psychological challenges like, for example, throwing everything away and trying again. When a start-up or product team realizes they’re headed nowhere and decides to change everything, the loss of years of work combined with the feeling of starting all over again is soul crushing. And yet, some of the greatest modern companies we know and love today were second incarnations of completely different ideas. YouTube was originally a dating site that never took off, despite relentless efforts to get people to sign up. Twitter started as a podcasting network called “Odeo” that was going nowhere, and Instagram’s team started with a hard-to-use check-in game called “Burbn.” Instagram as we know it today was an attempt to salvage the situation, designed with such extreme simplicity as a reaction to what they had learned the hard way with Burbn. In each of these cases, we tend to celebrate the breakthrough products without fathoming how hard it must have been to keep the faith and start from scratch. I’ve heard cofounder Kevin Systrom discuss how difficult the decision was, even though Burbn was going nowhere. Such bold moves are psychologically toiling, and while common sense may suggest otherwise, you must be committed to the suffering. Despite whatever hacks and strategies you employ, you will get burned repeatedly. Society’s immune system is powerful and indiscriminate. Suffering is inevitable, but by expecting it, you can manage your expectations and those of your team. You can build a culture that is as much about the experience building the product together as it is about the product itself. By doing so, at least you’re in your own little world suffering among friends! As you hire people to join you, you can evaluate not only their skills and interests but also their tolerance and commitment to enduring the fight against the self-doubt and gut-wrenching hardships that real life and society will throw at you.

Friction brings us closer. Our aversion to obstacles, setbacks, disagreements, and other forms of resistance is a bit ironic, because this friction is what builds our tolerance for future friction. We expend so much energy avoiding friction rather than inviting and leveraging it. The old adage “Friction polishes stones” is true: Friction not only reveals character, it creates it. By avoiding conflict, we don’t smooth out the rough edges of our ideas and plans. In Quartz, Hugo Macdonald, the former design editor of Monocle magazine, made the case for friction: The thought of friction may make us bristle, but it’s not synonymous with difficulty. The standard linguistic definition recognizes this: Friction is derived from the Latin word fricare, meaning “to rub,” and . . . generally means a force that opposes relative motion between two objects. Rubbing in opposition to something instinctively sounds like an undesirable experience—a disagreement, a struggle, a fight—and so over time, we’ve come to connote friction with negativity. But on the whole, rubbing things together creates, not destroys. Friction gives us heat and fire. It quite literally moves mountains. Rubbing two people together may cause arguments—but it also makes babies. Friction is a positive force in all walks of life precisely because it’s only when we’re in opposition to something that we learn how to move forward. In order to advance both individually and societally, we need more friction in our lives, not less. The aspiration for a “frictionless” experience is shortsighted. A truly frictionless experience, where you avoid or deny every ounce of struggle, is mindless. Friction makes you feel the texture of a process, and the texture helps you remember what you’ve experienced. Without friction, teams are liable to move too fast, and edges that are too smooth fail to form sustainable bonds. Hardship brings your team together and equips you to endure for the long haul. The upheaval of ordinary life causes a group of people to overlook their differences and unite around common causes. Bonds forged through adversity are most apparent when calamity strikes. Whether in wartime or after a natural disaster, shared struggles bring people together. I remember walking through the streets of Soho during the massive New York blackout in 2003 and saw stores giving away drinks, random civilians helping direct traffic, and everyone talking with one another. Friction unlocks the full potential of working together. When triggered, your ancestral preference for group survival through collaboration over isolation aligns interests in a powerful way. “When staying alive is not just the responsibility of the individual, but other members of the species help the individual to survive, and vice versa, all members’ chances are enhanced,” explains Richard Taflinger, a professor at Washington State University. The more a group cooperates, the more resources it can accumulate, the more territory it can defend, and the more it can protect itself from predators; those who stray from cooperation threaten the majority’s safety, motivating the majority to eliminate them. Cooperation is a natural instinct, and friction brings it to the surface. The more neurally complex the animal, the more social groups are used to enhance survival. Humans band together for physical and psychological protection. “In ancient history and prehistory, tribes gave visceral comfort and pride from familiar fellowship, and a way to defend the group enthusiastically against rival groups,” E. O. Wilson, a biologist, writes in Newsweek. “Modern groups are psychologically equivalent to the tribes of ancient history. As such, these groups are directly descended from the bands of primitive humans and pre-humans.” However complex these societal groups become, our psychology remains wired on the principle that groups equal safety. So instead of facing adversity solo, we instinctively look for groups, for comfort and restoration. Speaking on Harvard Business Review’s IdeaCast about a book he coauthored with Sheryl Sandberg—Option B: Facing Adversity, Building Resilience, and Finding Joy—Adam Grant, a renowned organizational psychologist and Wharton professor, describes the business incentives of group support. Studies show that when companies provided assistance programs that offer financial support and time off when employees faced unexpected adversity (such as if their home was damaged by a natural disaster or a relative fell sick), “it actually paid dividends in that people felt like they belong now to a more caring company,” Grant says. “They took pride in their employer as a really human place to work. And they were more committed as a result.” Sheryl Sandberg, Facebook COO and whose personal experience of her husband Dave Goldberg dying suddenly was the inspiration for Option B, recalls, “I never would have gotten through this without Mark [Zuckerberg]. Mark was at my house the day I came home from Mexico and told my children. Mark literally planned Dave’s funeral. And Mark was with me every step of the way. When I came back to work and felt like I was a ghost and no one would talk to me, I took refuge in his conference room. . . . We think about providing that kind of emotional support to our friends. . . . But we can also do it at work. And it makes us closer to the people we work with. And I think it builds a much stronger organization.” Groups help us manage life’s frictions, and the challenges we face bring groups together. Rather than circumventing or burying it, use the frictions you encounter to learn how to cooperate and build your team’s capacity to handle adversity. Whatever you do, don’t fear tension and confrontation. Passivity arrests your development as a team. The fights bring you a level deeper, they force you to cover more surface area of opinion so you can ultimately discover the best solution. And, often times, we desperately need the clarity that crisis provides. As the early Roman emperor Marcus Aurelius once quipped, “The impediment to action advances action. What stands in the way becomes the way.” Indeed, the frictions we encounter help us find a better way so long as we face them.

Darviridis commented 9 months ago

Be the steward of perspective. The middle of a venture is like a lengthy road trip without windows. It is psychologically torturous to travel without any sense of where you are along the way—no sense of progress or landmarks—and without a sense for how many miles remain. Your concept of time becomes warped, and impatience stews. Teams need to be reminded where they are and what progress they are making. As a leader, you are your team’s window. You need to call out and describe the landmarks that you pass along the way, constantly reinforce the terrain you have already covered, and prepare folks for the map ahead. Reporting facts and managing expectations are only a small part of this job. More important, you are a storyteller. Your job is to make history more interesting and relevant when retold than when it happened. After all, the middle of a journey is a blurry, mundane landscape. To get through the tremendous voids of nothingness in between the milestones, provide guidance. You’re the narrator of this journey. People who worked with Apple founder Steve Jobs over the years often talked about how his “reality-distortion field” could alter his team’s perspective, assumptions, and limits to allow for new ideas. Perhaps Jobs believed in his vision so much so that the reality around him was distorted by the power of his conviction? When you’re articulating a vision and set of assumptions with such passion and confidence, reality starts to bend your way. You’re not lying or manufacturing perspective—you’re merchandising your perspective. You’re not creating a story that you think others will believe—you’re retelling the same story you tell yourself. The same forces can help a team endure another form of reality: work with no end in sight. In this case, your reality-distortion field shows people hope when they can’t see it for themselves. For example, you may see these tough days you’re currently enduring as character building for your team and as a source of defensibility for your product—even though it currently feels anything but. Are you lamenting a lack of progress or celebrating your survival and newfound strength? Are you merchandising hard work as tiring or as achieving defensibility in your market? As you summarize your team’s exhaustive work and struggles over the months or years that have passed, conjure up the perspective that excites you the most, and then share it. Storytellers make the past relevant to the future, even when it is dry and irrelevant. Likewise, it is your responsibility to steward perspectives when you’re not even sure the conversation will end in a solution. Some of the best conversations are ones that are not trying to answer a “yes or no” question. In such conversations, instead of prompting closure, your goal should be to lead your team through a process of self-discovery. Conversations with no near-term actions or solutions reveal the surface area of the issue—blind spots, wrinkles, and unexpected edges. But, if nothing else, the ongoing discussion supplants ambiguity and any “elephants in the room” by keeping the team engaged and motivated. By participating, everyone feels more in control of their destiny. Especially when failures or major setbacks occur, you need to carry your team through it. For example, imagine working years to launch your product to much fanfare and then suddenly having your product shut down by the government for a couple of years. That’s exactly what happened to Anne Wojcicki, CEO and cofounder of genetic testing company 23andMe. Founded in 2006, 23andMe allowed customers to spit in a small tube and, within a few weeks, get access to a wealth of genetic information about their ancestors, predisposition to health issues, and other insights based on their genes. The company thrived in its early years, attracting excited customers and some of Silicon Valley’s greatest investors. But then, in 2013, the U.S. Food and Drug Administration (FDA) abruptly ordered 23andMe to discontinue marketing its personal genome service, based on concerns about the potential consequences of customers receiving inaccurate medical results. For two years, the company conducted the necessary research and addressed the FDA’s concerns, until October of 2015, when 23andMe announced that it would be offering a revised health component with FDA approval. In retrospect, this major blow to the business and the team’s morale may be nothing more than a blip in the company’s early history. But how do you manage such a setback when it happens? As Anne recalls, the team was so bought into the mission that they were largely undeterred. “The more passionate you are about the cause, the less hard it is,” she explains. “When you have so much conviction that you’re doing the right thing, you see such a challenge as part of the process rather than a road block. We were used to people not understanding us or not liking us, so our attitude was always ‘We need to prove it to them’ versus ‘What are we doing wrong?’ With enough conviction, you can cut through ambiguity.” As for helping a team reach and sustain enough conviction to endure such setbacks, Anne believes it comes down to the people you hire, how you communicate, and decisiveness. “From the very beginning, we’ve wanted people that really believe in the mission. If you have FOMO [“fear of missing out”], go elsewhere. We are impacting lives of people and transforming health care. Everyone here knows the mission and my job is to reflect it. During regulatory challenges, we didn’t lose many people. I would go around the company and remind people, ‘We’re on the right side of history.’ This was our mantra, and we needed to take another path forward . . . it was a matter of our first path being wrong, never our mission being wrong. We wavered only on how we were going to get there but not the endpoint.” By luring new employees with your mission, as opposed to flashy titles or the best compensation package, you’ll build a more durable team that is willing to try different paths to achieve the mission they signed up for. But still, your perspective during the most difficult times will help your team defy their own self-doubt. When distractions and drama arise, acknowledge them, and then recontextualize them so that the suffering pales in comparison to the broader opportunity before you. Remind your team why you’re all there. They signed up to work with you because they believe in your vision and want to make something extraordinary. Your story has more gravity than you realize. Your job is to help your team make sense of the strategy—what they’re seeing, doing, and working toward. You are the steward of your team’s perspective, and there is always a way forward so long as you explain it.

Leave every conversation with energy. Whether you’re building a new business or transforming an old one, you’ll face an endless battery of painfully long conversations that have no outcome. Unresolved conversations are draining. People want resolution, and they want the confidence and motivation that comes along with a clear plan. As a leader, you can’t always provide answers. And you shouldn’t, as the correct solution may still be premature. But what you can do is always add energy. This ability to turn negative conversations into positive ones is a trait I’ve always admired. My former colleague David Wadhwani is especially adept at this. Before he became CEO of AppDynamics, an enterprise software company in Silcon Valley, David ran the digital media portion of Adobe when I joined the team after Behance’s acquisition. At the time, the company had just begun a historic transition from being a traditional software company that sold boxed software to being a services company that offered customers a series of services for a monthly fee. Adobe was one of the very first publicly traded software companies to make this transition and faced tremendous risk in doing so. David had the difficult task of leading teams of Adobe veterans, most of whom had been at Adobe more than a decade, to make the requested changes to their products. While the company had changed directions, many in the ranks were still resistant. The implications were far reaching, and some product leaders were neither prepared nor willing to rethink their products. The teams were not equipped for the onslaught of challenges. Every Tuesday at David’s staff meeting, we would untangle these problems and discuss paths to resolution. We usually realized that things would get worse before they got better. Many meetings, every option was a bad option, but we just needed to take the steps to keep pushing forward. Despite the circumstances and solemn sense of many of these meetings, David had a way of leaving every meeting on a high note. He would acknowledge the challenges before us while reminding each team why their work was important and what success would eventually look like. Even after painful meetings that lasted multiple hours without any sense of closure, David still managed to bring it together at the end in a way where we all left with energy—something along the lines of, “Hey, I know this is rough and we’ve got some serious work to do, but I also know we’ve got a good plan and the right people,” and adding something funny and uplifting at the end. Your job is to be an energy giver rather than taker, which is common among founders and leaders I admire. Chief among them is Jon Steinberg, the former president of BuzzFeed who went on to found the news media network Cheddar. Those who know Jon will attest that he is a force of nature. Every team pep talk is an infusion of energy and insight about why the “old model” of cable news is wrong and why Cheddar is the pioneer for the future of the industry. If an idea from his team is great, he’ll turn the company on a dime to make it happen. Having served on Jon’s board, I have witnessed firsthand how he motivates his team, board members, and clients. The common theme across interactions with Jon is that he’s all-in, all the time. When Dunkin’ Donuts became a big Cheddar client, Jon started wearing Dunkin’ apparel, catering every meeting with Dunkin’ Donuts and coffee, and sharing weekend shots of his family at Dunkin’ on Instagram. What better way to infuse energy into a partnership and send a clear message to current and prospective clients that Cheddar values loyalty and service? He turns every milestone into a source of energy rather than a celebration. When a record is broken, he’ll follow with something like “That looks pretty fucking awesome to me. Who else is achieving these goals on average? Nobody. Look at that trend line. . . . I know it’s a lot of stress, but it’s working. Hold yourself and your colleagues and me accountable for great content AND views AND deals AND more hours of LIVE! . . . Let’s push harder, fight harder, keep the trend going!” When you leave a meeting with Jon, or read an email from Jon, you have more energy than when you started. Your team needs energy transfusions, especially in the middle miles when circumstances feel dire and there is no end in sight. Acknowledge the trials and uncertainty you’re facing, followed by reiterating your plan of how to climb out, what you’re aiming to achieve, reminding your team why you’ve come together to do that, and then add your own enthusiasm and confidence. In the final moments of every meeting and communication, you need to reiterate purpose and leave people with the energy to achieve it.

Darviridis commented 9 months ago

If you don’t like the way government is being run, cross party lines. For all the criticism they get, big companies have a tremendous opportunity to make a global impact. The bigger you are, the more muscle you have to force a new idea into existence. But size typically works against us. Just as weight lifters’ bulging biceps make them great at lifting weights but terrible at scratching their own backs, larger companies tend to gain weight disproportionately and trip over themselves. I have come to call it corporate obesity. If you’ve worked at a heritage corporation, you’ve probably witnessed the following phenomena: Discussions are more about who owns what and who reports to whom rather than how you are going to make something happen. Emails are more about who should solve problems than how to solve problems. Teams spend too much time figuring out how to circumvent other teams to get something done rather than getting everyone aligned. The BCC field gets too much action, and emails typically end with passive-aggressive (or sometimes just plain aggressive) comments or condescending questions. People act one way in meetings, another way out of meetings. When you question people, you offend them rather than engage them in a constructive debate. You often nod your head or stay silent when you disagree for fear of retribution. When working in an environment filled with these behaviors and tendencies, progress slows to a painful crawl and talented people lose their energy and imagination. Not every big company suffers from corporate obesity, but they’re susceptible to it unless leaders willfully seek to feed their teams a healthier diet. After my first six months at Adobe, post-Behance’s acquisition, I was asked to take over the mobile and services portion of Creative Cloud. I quickly became mired in questions around who should be in charge of what and who should and shouldn’t work with whom. I faced a decision: Do I play within the entrenched politics by respecting the layers of management and the chain of command I had walked into? Or do I try to find the right people across the organizations, regardless of whom they reported to, and get them talking? At the time, it wasn’t an obvious decision; the pressures of a big company are real, and it is tempting to adjust and avoid stepping on toes by not stepping across party lines and respecting an organization’s existing political structure. I decided to eschew the operating system I found myself in and created my own. After I had identified the people I thought could help us achieve our goals, I needed to work out how to break them free from hierarchy and bureaucracy. To engage key people from other parts of the organization, we invited them to our meetings, despite reporting lines. We kept all interested parties included on communication lines, regardless of whom they reported to. Rather than focus on the senior leaders of every team, we sought to engage the people who were closest to the technology and had their team’s respect. Rather than have product leaders present designs, we brought in the actual designers to present their own designs. I encouraged my leadership team to speak up right away if something didn’t make sense. And I pushed all of us to have in-person conversations when disagreements came up. There were fits and starts, but we ultimately grew a team of hundreds of people who were remarkably aligned and effective. I realized that the politics of the organization encouraged people to

focus on small and less disruptive wins rather than make a dent in the more controversial, and more important, problems. It was easier to let conflicts linger than wade through layers of management and follow up on communication lags. We had to break these barriers to make progress— without breaking the organization. We picked our fights carefully. Of course, much of this is easier to implement as a senior leader in an organization, but the same principles can be fostered from junior ranks as well. It starts with building your own relationships with people in different teams across your organization and proactively serving as an ambassador, connecting the right people to expedite solutions. Just a year or so later, in 2015, a special moment happened when a senior designer on the team, Eric Snowden, was onstage demoing our new products in Apple’s keynote for the launch of the first iPad Pro. Another member of my team, Govind Balakrishnan, who ran all of engineering for our group, walked over to me and commented that he still couldn’t believe it had all come together. We recalled some of our most trying moments and how daunted we felt at the beginning when all of this was a sketch on a whiteboard. Sure, there were fights for head count and debates about reporting lines and priorities across different teams, but we had aligned enough people to use the organization’s weight in our favor. Now, with a whole new suite of applications and a clear strategy, our team was part of Apple’s keynote—which carried extra significance, given Apple and Adobe’s long-standing feud over Flash, which was now, finally, water under the bridge. In a big company, change causes some degree of disarray and often requires many people and processes to shift. Given these circumstances, it’s tempting to stay safe by adhering to protocol, hierarchy, and process. But by doing so, it is more difficult to get the right people talking to one another. It’s more important to be collaborative than to be correct. If an organization doesn’t let politics and burdensome processes get in the way, then size becomes an advantage. If not, well . . . big companies become couch potatoes while the future of their industry passes them by. Of course, this all comes down to the leaders themselves and whether or not a culture supports people stepping out of their traditional roles. Fight corporate obesity by gathering the right people in a room and depoliticizing process as much as you can.

DYFJ. Do Your Fucking Job. Every journey has heavy, all-consuming moments. Firing employees. Solving a PR crisis. Weathering legal battles. On such occasions, you’ll struggle to push through the muck. You’ll fret the aftermath of confrontation. You won’t want to upset people, especially those who may be left without jobs because of your decisions. You’ll find every reason to analyze further, delay action, and blunt the blow. But most of the time, the right answer is clear, and the next step is yours. You need to do your fucking job. This is what I would tell myself before going into a tough meeting, nail-biting negotiation, or making the decision to fire an employee. Whenever I needed to force myself to take action that would be painful in the short term but was for the greater good, I would whisper to myself, “Scott, do your fucking job.” Don’t blame yourself for feeling skittish. Avoiding conflict and hesitating before you disappoint others is not a weakness, it is having a conscience. Relationships matter, and the cost of upheaval in any relationship or team culture is very real. But just as a common cold can become full-blown pneumonia if left unchecked, infections in a team grow when not addressed. Your job is to detect infection, determine whether it is viral, and nip it in the bud if it is. Leading a team through enduring times requires many “rip off the Band-Aid” moments. Nobody wants to inflict pain on their team, but quick and controlled pain is better than a drawn-out infection. If the cost of waiting exceeds the benefits of acting now, you have a job to do—DYFJ! In the middle of 2017, the cofounder and CEO of a fast-growing start- up in the social video space reached out to me for some help. We had met only once or twice and I was not an investor in his company at the time, but he asked if we could talk. We met at a small coffee shop in New York City’s Soho neighborhood to discuss his dilemma. A senior member of his team had been accused of inappropriate behavior from some of his subordinates and a short investigation had confirmed it. His board members were urging him to hold off on any “rash” decisions because of an imminent round of financing and the company’s recent traction. But that didn’t feel right to him. He was struggling between what he knew, in his gut, he must do, and all the noise from investors and the usual anxieties that accompany decisions that cause a lot of turbulence. As we talked through the costs and benefits of waiting and how to start these conversations, it occurred to me that he didn’t need any more rationale to fire the person. Rather than continue thinking about the repercussions and his discomfort with the decision he already knew was right, he had to just do it. He came to this conclusion on his own, and as we parted ways, I said, DYFJ, and he nodded. Perhaps all he needed was a reminder that some critical tasks— often the most difficult ones—will not be taken until the leader summons the courage to stop considering it and just does it. During the most trying times, you may also struggle to remain composed and continue carrying the torch. While members of your team will express doubt and air their hopeless moments, you will need to keep the pace by keeping the faith. One of the entrepreneurs I have admired over the years is Kegan Schouwenburg. After some time working at Shapeways, a 3D printing company, Kegan set out to found her own business designing custom orthotics. Her company, SOLS, was on a rough ride: Kegan had to fire a cofounder, shift the business’s focus multiple times, and land subsequent rounds of funding at a time when it was hard to raise money for hardware start-ups. While her business was ultimately sold, which wasn’t the outcome she had hoped for, I was especially struck by her persistence and positivity along the way. Reflecting on some of her most challenging periods in the business, Kegan recalled, “One of our ex-employees told me in passing recently that I used to sing under my breath, ‘Just keep going.’ Honestly, I think that is most of it. You just have to show up and be there because your team depends on you. When you’ve got your entire staff looking to you for leadership, listening to your language, and even your body language to give them a sense of confidence in what you’re doing as a company, that responsibility really gives you the energy to power through the uncertainty.” “It’s amazing what you can achieve if you refuse to be discouraged, refuse to let down your team, and you check your ego at the door,” Kegan added. Indeed, the possibilities are endless if you just keep going and, at your most difficult and trying moments, push yourself to do your fucking job.

Darviridis commented 9 months ago

The only “sustainable competitive advantage” in business is self-awareness. Your sense of self shifts when you’re at a peak or in a valley. During great moments, we are liable to have an inflated sense of self. We believe we are right more often than we actually are. As both a defense mechanism and the presumption that we should just continue doing what we’re doing to keep climbing, we become less open to the advice and signals around us. We start to believe the nice things people say about us and become too confident in our own abilities and less in touch with reality. Similarly, in difficult periods when we are struggling to find the motivation and direction to move forward, we can become less aware. When we stress, we regress. As our strengths become weaknesses, our superpowers turn against us when we feel vulnerable. We blame people and forces around us as a way to maintain our confidence and the soundness of our plans. Self-awareness starts with the realization that when you’re at a peak or in a valley, you’re not your greatest self. When things are going well, ego gets the best of you. When times are tough, insecurities run rampant for everyone involved. Only by recognizing these shifts in ourselves and others can we manage them and protect the integrity of our judgment and actions. We are not necessarily the cause of the situation, but we are the cause of how we see it. Our perspective is our promise or peril. With such insight, you can more carefully vet your reactions and decisions when things are going very well or poorly. Effective advisers and boards are most helpful at the extremes, when the tough questions are less apparent but critical. Self-awareness means understanding your own feelings enough to recognize what bothers you. Whatever triggers your frustration or irritates you is rooted in a core value you have, something you vehemently stand for or against. For example, injustice really bothers me. Whenever I see unfairness, I need to right it. When I am taken advantage of, I will opt to right the wrong even if the economic cost of doing so exceeds the economic impact of letting it go. This behavior could potentially be destructive, and it is tied to one of my core values. But now that I have made myself aware of it, I can see it bubbling up in myself and learn how to mitigate it. At least I try. Being conscious of your triggers helps you take your finger off that trigger. Self-awareness means being permeable. An undeniable theme among founders I’ve worked with is that the less defensive they are, the more potential they have. Those who are able to openly absorb and selectively integrate what they hear consistently outperform those who are impermeable to suggestion. I deeply admire founders and designers I have worked with who seek feedback proactively. But being open-minded while receiving constructive criticism is challenging. When you feel criticized or attacked, what happens? Do you immediately try to explain yourself? Do you go on the offensive and try to fight back? Do you become reclusive and try to avoid the conflict altogether? Do you become more steadfast in your ways, or are you too shaken and too impressionable? Self-awareness helps you achieve balance between these tendencies. If you acknowledge your behavior when it happens, and then investigate what is driving it, you will become more open to the right insights from others. Self-awareness comes from chronicling your patterns. The insecurities, brash reactions, and self-doubts that emerge in difficult times are reflexes that started long ago. The leaders I admire most have invested a great deal of time understanding their own psychology and unpacking their past. Whether through executive coaching, psychoanalysis, or some form of group therapy, your effort to understand how your own mind works is the only path to reliable self-awareness during times of stress. Understanding the sources of your own negative tendencies also helps you make sense of others’ behavior. As psychoanalyst Carl Jung, who founded the field of analytical psychology, once said according to numerous accounts, “Knowing your own darkness is the best method for dealing with the darkness of other people.” Being in touch with your own flaws helps you support others with their flaws. Discussing your flaws invites others to do the same. Self-awareness means dispelling your sense of superiority and the myths that people believe about you. With any achievement, we’re liable to overestimate the role we played in it and underestimate the role of others—and of luck. By doing so, we alienate those who did contribute and become less relatable. We obsess over ourselves a bit more and tune into others a bit less. I have watched a number of successful artists and entrepreneurs I know become more isolated and paranoid as they became well known. Perhaps they begin to question the motives of everyone around them, or perhaps they start to believe they are superior. Regardless, the result is a loss of genuine connection with the people who helped launch their careers and, with it, empathy. Without empathy for others’ problems, ideas become less viable solutions. The trick is to integrate humility in your life. It could be a sense of spirituality that keeps you open, a partner who keeps you grounded, or an insatiable sense of curiosity that keeps you inquisitive. Attribute your wins to those around you, and be the first to take responsibility for losses. Ultimately, self-awareness is about preserving sound judgment and keeping relatable and realistic. However big your project or ambition, your journey is nothing more than a sequence of decisions: You’re probably many decisions away from success, but always one decision away from failure. Clarity matters. The more aware you are of yourself and your surroundings, the more data you have to inform your decisions, and the more competitive you will be. Nobody remembers, or is inspired by, anything that fits in. If you’re building a new business, you’ll be tempted to describe what you’re making in the context of what already exists as a shortcut to relatability, like the “Uber for massage” or the “Apple of razors.” The pressure to conform stems from the natural desire to be understood. But what you gain in relatability by latching onto an existing model, you lose in free-range innovation. One of my favorite thinkers on this topic is James Victore, a widely respected designer who has committed a part of his life to educating the next generation of designers. I’ve attended workshops that James puts on for his students, and a theme throughout is resisting the urge to fit in. I asked James to explain why he seeks work that, at first, strikes others as strange, and how he handles it: I do the work I do because I have to. I can’t help it. I was born this way—I can’t be false to any man. I know what the current trends and moods are, but I can’t concern myself with them. I also can’t force myself (as many do) to make work that fits within the going commercial style. Trends change, and I believe that is why my work is still relevant today, because I am the only one making work like mine. The idea of being born “weird” means you have a gift— like being born a star athlete. It would be a sin to deny my gift. My “weird” is powerful. It stands out. I know that it attracts some individuals and clients, and repels others. I have to be cool with that. I am not for everyone—just the sexy people. Like you. When you pursue something on the fringe that uniquely fascinates you, you’ll repel those who just don’t relate. You may be shunned. And most people won’t understand. But the future always starts as fringe. When front- running the future, the trick is to aspire for a small audience that loves your product rather than aim to please the masses. James wants us to find peace with our “weird.” Embrace the stuff you’re most proud of that others don’t understand because this is your proverbial ticket. But more important, James is pushing us to use weirdness and the rejection that comes along with it as a barometer for our originality. Are you seeking acceptance too early in your project? Are you too deterred by being misunderstood? Are you trying to normalize what you’re making and, in the process, regressing to the mean? Don’t succumb to society’s gravitational force toward what is common and familiar. One of the worst tendencies of the messy middle is pulling wildly fresh insights back toward the mean of normalcy. Don’t let this happen to you. While society wants you to conform, it needs you to break the mold to help us see differently and make life better for the rest of us. And as American artist Sol LeWitt once advised, “Learn to say ‘fuck you’ to the world once in a while.” Do your thing.

Take a dose of OBECALP and suspend your disbeliefs in yourself. My father, who began his medical career as a surgical intern in New York City’s Bellevue hospital, has experienced many intense nights in the emergency room, where patients have come in suffering from drug overdoses and other dire situations. During his time in the ER, he told me about the administration of a particular dosage of “OBECALP,” which was either administered intravenously or as a pill for patients suffering from the anxiety that accompanied their physical or mental afflictions. After a dose of OBECALP, most people would calm down and engage in conversation with the medical staff. OBECALP is, of course, placebo spelled backward. Over the past two decades, many clinical trials have shown that the strange effects of placebo sugar pills are getting stronger. In a 2015 study, published in the journal Pain, researchers found that in 1996 drugs relieved pain 27 percent more than a placebo. But in 2013 that gap had fallen to 9 percent. Stranger still, this effect has been observed only in the U.S., which is one reason why pharmaceutical companies are struggling to get new painkillers through trials. Nevertheless, placebos are powerful. Sometimes patients need the hope that a placebo provides to recover. In tough moments when your prospects feel grim and hope is fading, your mind will only make it worse. You’ll begin to question your ideas and tell yourself that you’re not qualified and that your team isn’t good enough. You’ll become your own worst enemy and you’ll stop believing in your own plan and abilities. When this happens, what you need is 20 milligrams of OBECALP. Stat. Imagine, for a moment, that all your self-doubts are simply a function of society’s immune system, designed to extinguish nonconforming actions. You’re questioning yourself because you’re doing something different and society is trying to stop you—your body is trying to reject the thing that is taking it out of its comfy homeostasis. There can be only so much innovation and change in a world that runs on consistency and people falling in line. Remind yourself that progress is vision paired with initiative. The hopelessness you’re feeling is a common phase that precedes progress; we often feel the weakest just before our immune response kicks in. Sometimes you need to make yourself swallow a big OBECALP to get through that time. A big part of overcoming doubt is suspending your disbelief. You want to stay grounded as you make decisions, but sometimes you need to escape the gravity of reality to imagine the possibilities. A friend who worked for Google cofounder and CEO Larry Page told me that when teams presented product and business goals to Larry, he would often reply, “What would it take to achieve 100x of what you’re proposing?” This was totally unrealistic, of course. Such questions would throw teams off their tracks, but the notion of aspiring for an entirely different magnitude of impact had some important side effects. First, whatever doubts teams came in with suddenly paled in comparison to the new concern. Second, teams were forced to question their core assumptions and untether themselves from reality’s gravity. In some ways, Larry was administering a dose of OBECALP to suspend his team’s disbelief and recalibrate their ambitions. Your challenge is to work out how to administer your own placebo. Perhaps it is a bold narrative your team replays about what it will look and feel like to see your future product out in the wild? Perhaps it is your efforts to merchandise contingency plans so people can move forward with less fear? When you envision what is possible in a state of suspended disbelief, you free yourself from your previous petty problems. Once you have that goal in mind, you then should attempt to execute it as practically as you can. You don’t know what you’re capable of. Whether it is navigating your career, starting a new business, or overcoming an illness, giving yourself a placebo of sorts that suspends your doubt is one of the greatest factors in making progress.

Attempt a new perspective of it before you quit it. When times are truly rough, when should you stick with it, and when should you quit it? In her late twenties, Angela Duckworth quit her job as a management consultant to teach middle school math in New York City. She observed that students’ success was determined by their effort more than anything else. Intrigued, she began studying why some people work much harder than others, and she enrolled in the University of Pennsylvania’s psychology PhD program. In 2016, she wrote Grit: The Power of Passion and Perseverance about her findings. Duckworth explains that what determines whether you succeed or fail is grit, a special blend of passion and perseverance directed at accomplishing long-term goals. “Grit is having stamina. Grit is sticking with your future, day in, day out, not just for the week, not just for the month, but for years, and working really hard to make that future a reality. Grit is living life like it’s a marathon, not a sprint,” Duckworth said in her 2013 TED talk. But working hard doesn’t mean showing no pain or pretending all is well. Duckworth clarifies in a New York Times interview that “when you look at healthy and successful and giving people, they are extraordinarily meta-cognitive. They’re able to say things like, ‘Dude, I totally lost my temper this morning.’ That ability to reflect on yourself is a signature to grit.” In the middle of any journey you’ll wonder if you should just give up. It can be hard to see in the moment, but your struggle may mean you’re onto something new that is defensible from competitors and copycats. The question is whether you’re close to the tipping point of the project working and the difficulties you’re experiencing are just wearing you down, or if they’re rightfully making you question your true belief in the final vision. It’s extremely difficult to halt all progress and start all over again, but the boldest projects have multiple such “resets.” Perhaps one of the most challenging and important consumer product creations of our lifetime was the iPod, and subsequently the iPhone. So I asked Tony Fadell—who, before creating the thermostat company Nest, was brought into Apple by Steve Jobs to lead the iPod project, and then iPhone—about how his teams worked their way around so many dead ends. Tony explained, “I think there are two kinds of resets, one which is product spec based, not meeting the customer needs, and the other which is engineering based, not having a way to implement the plan with the current team or current technology inside or outside the company. We did a lot of resets along the path from iPod to iPhone, like going from iPod to an iPod Phone, to an iPod with a big screen, to a touch screen Mac, and then putting it all together to make iPhone—always searching for the right mix of technology and user experience.” It sounds like a normal process in retrospect, but spending months if not years pursuing one path and then hitting the reset button can exhaust and demoralize a team. But Tony felt that, so long as you’re gaining confidence in the opportunity and absorbing the lessons learned, you have a renewable energy source. “In most cases, if the fundamental reasons for why the product or service should exist are still valid, then the team will always take on the challenge, assuming you didn’t burn way too much time or cash and it was an intelligent—albeit sometimes crazy and unexpected—way to get to the learnings. We all, as a team, did a conscious recommit at the end of each one of these ‘resets,’ or what I call ‘learning phases,’ to describe the lessons learned, what assumptions have changed, and which ones didn’t, to muster the energy to make another go at it.” The trick is to separate the hardship from what you’re learning. If you’re learning that your assumptions were wrong—that customers don’t want your product or that you’re building the wrong thing—then you should ask yourself: Knowing all that I know now, would I pursue the project all over again? Would I invest the money and energy all over again to get as far as I’ve come in solving this problem? If the answer is yes, don’t quit. Keep at it. Feeling impatient with progress and deflated by process is fine, so long as you still have conviction. But if your answer is “Hell, no! If I could go back to the day before I got into this mess, I would head in a totally different direction,” then ask yourself why you are still trying. Are the sunk costs keeping you from quitting? Are you still going only because of how much you’ve invested in it so far? Is it just ego? Try not to value the progress you’ve made thus far based on how hard it was and what leaving will cost you. I’ve never been fond of the “winners never quit” mantra because it goes against what I’ve learned from many successful start-ups that pivoted from their original idea with great success. Twitter, Pinterest, Airbnb, and many other companies started with either a different approach or a vastly different product before they got it right. If you’ve lost conviction but refuse to change course because of what you’ve already invested or achieved, then you’re officially doing things for the wrong reason. As you contemplate new approaches to a problem rather than quitting altogether, it’s important to let go of past conclusions proven wrong. One of my friends who worked at Apple for a number of years recalled Steve Jobs’s ability to change his mind on the turn of a dime when a better solution was presented—he didn’t get stuck with an operating mode just because it had been one that was working. He had famously strong opinions, but he was also able to detach from them. In this way, Steve was the embodiment of the famous advice to have “strong opinions, weakly held.” Only by letting go are you able to truly attempt a new perspective of your venture before you quit.

Darviridis commented 9 months ago

To create what will be, you must remove yourself from the constant concern for what already is. The spring of 2015 was one of the most exciting albeit challenging periods of Alexa von Tobel’s life. Just off a $35 million financing round for LearnVest, a company she had launched exactly five years earlier to help American families with financial planning, Alexa was fielding multiple acquisition offers. She was at a critical juncture in the company’s growth and has just finished overhauling her management team. She was also expecting her first baby any day. On top of it all, Alexa was still on the line to manage her team and continue her role as a very public face for the company and, increasingly, for the financial industry. “In a weird way, the level of craziness provided an even greater sense of perspective and judgment,” Alexa explained to me. “I kind of felt like I was doing an Ironman—you can’t get too stressed about a few miles of swimming or the hundred miles of biking, because you’ve got a marathon waiting for you after that. The fact that such extreme things were happening at the same time conjured up a forced sense of perspective and calm, reminding me what really matters and preventing me from getting too consumed by any one of the challenges I was facing. If bad decisions are made when we lose perspective, then facing all of these important moments in my life—all at once—was a good thing. Paradoxically, the busier you are at any moment in time, the better your decisions may be because of the greater perspective you have. Bringing life into this world, unsurprisingly, brings perspective.” O The many challenges Alexa faced kept her from becoming overwhelmed by any one of them. Alexa was able to compartmentalize and focus on each with an eye toward the future. In her decision to sell her business, she focused on the three constituencies she served—shareholders, employees, and clients—and led a process that proved successful for everyone involved. Alexa sold her company, LearnVest, to Northwestern Mutual on a Wednesday for a reported $350 million and then went into labor on Sunday. Alexa kept a longer-term perspective and managed each challenge on its own. When viewed in context of her ultimate goals—becoming a mother, leading her team, and ensuring a good outcome for her company— the day-to-day issues were dwarfed. As you encounter such periods in your own career, compartmentalize each drama individually and remind yourself on the horrible days that tomorrow will be better. Compartmentalizing doesn’t mean burying or denying the emotional toll; it means facing one challenge at a time and using each one to provide more perspective for dealing with the others. Storms have the habit of feeling like their own little worlds, even though they’re just weather patterns and they move on. Compartmentalizing is just as hard on a daily basis as it is during a perfect storm. The more responsibility you bear, the more your collective concerns will limit your productivity. To move forward, unbounded by the anxieties and insecurities of the moment, you must apply controls to the energy you spend assuring yourself that all is OK. TAKE NOTE OF YOUR “INSECURITY WORK” ver the years, I have come to recognize the amount of time I spend checking things: Daily sales data, website traffic trends, what people are saying on Twitter, analytics for our customers, team progress on projects, the list goes on. For you, it might be diving into a spreadsheet to manipulate budget numbers or scanning through your unanswered emails again and again. When you’re anxious about your business, there is no W easier quick-relief antidote than checking things. The problem is that you could spend all day checking things and fail to do anything to change things. I call it insecurity work—stuff that you do that has

  1. no intended outcome,
  2. does not move the ball forward in any way, and
  3. is quick enough that you can do it unconsciously multiple times a day. Insecurity work puts you at ease, but it doesn’t actually get anything done. The antidote is a combination of awareness, self-discipline, and delegation. Whether it is Googling the same search terms again and again or constantly checking your in-box as if it were a boiling pot of water, you need to identify these behaviors to then change them. When you spend 30 minutes going down a rabbit hole to answer a particular question, be sure to ask yourself, “Why is this question important and how is the answer actionable?” If the answer is just self-assuring but not actionable, it is likely insecurity work. Once you’ve identified your insecurity work, establish some guidelines and rituals for yourself. For example, you could allow yourself a period at the end of every day, say 30 minutes, where you let yourself go through the list of things you’re curious about. Put all of your mosquito bites in one place and allow yourself the pleasure of scratching them all at once. The purpose of reducing the hours you spend on insecurity work is to free up your mind, energy, and time for generating and taking action on new ideas instead of checking in on old ones. KEEP YOUR STARE AHEAD hether managing one of the most difficult periods of your life or just the everyday ups and downs, you can make progress only by focusing forward and removing yourself from the constant concern for what has already happened. During one of my recent trips to Japan, I spent some time at a Buddhist temple learning about rock gardens and the design practices behind them. In these gardens, small, finely washed rocks are immaculately raked into lines and curves that create remarkable designs around larger boulders that serve as the rock garden’s anchors. One Zen principle lies in the process of raking lines in the rock garden. If you focus on each line as you make it, it isn’t straight. Instead, you must focus ahead to keep the line straight as you rake. I was struck by how this Zen principle relates to leading a team through daily challenges while staying true to a long-term vision. If we rake with heads down, always concerned about the lines of stones beneath our feet, our lines run amok. The insecurity work we do every day is the equivalent of leading a journey focused only on what is immediately concerning us— beneath our feet—rather than focusing on where we want to be. But if you compartmentalize your ideas and look ahead, and worry less about day-to- day concerns, you’ll eventually look behind yourself to see the line you drew was much straighter. You will arrive much closer to your vision.

Prompt clarity with questions. Most of your experience enduring the middle miles will be couched with uncertainty. You’ll feel like you’re wading through an ocean of unknown depths and inhabitants—in the dark. But every now and then, a light goes on. Not a floodlight that illuminates the horizon but rather a spotlight that provides some context and comfort. In these rare moments, you suddenly get a sense of where you are, what is behind you, and what comes next. The teams I have led and advised over the years make a ton of progress in these moments of clarity. It is during such moments that they settle on the perfect brand, devise a truly differentiating feature, or make a crucial decision that completely changes the course of the project. But how do you find the light switch and not get temporarily blinded by the glare of opportunity? What prompts these moments of clarity, and how do you capitalize on them? I remember one such moment with the Periscope team in early 2014 before the launch of their first live-video product. This glimpse of light ultimately led to some drastic changes in their product, and ultimately their much celebrated acquisition by Twitter. When I first met Kayvon Beykpour and Joe Bernstein, Periscope’s founders, they were building a different product, Bounty. The original idea for Bounty was to allow anyone around the world to request a photo of a particular place or event and have someone close by capture the photo for a fee. The idea had potential, but a series of brainstorms within the team about the broader state of social media and the emerging field of live video transformed the entire premise of the company in just a matter of days. At the time, social media was mostly photos and prerecorded video. Whether you were using Facebook, Twitter, or Snapchat, the photos and videos you saw had already happened. As a result, it was hard to feel like you were actually there. When you witness an event in person, you connect and empathize with those around you. But watching a prerecorded video— or even live television that you cannot interact with—depersonalizes the experience. The Periscope team and I discussed the idea, coupled with the emergence of better bandwidth for mobile devices, and wondered, “As live video becomes more feasible, what kind of social experience would foster truth and empathy?” This crucial question prompted the vision of “teleportation,” where anyone could witness an experience through someone else’s eyes and interact with the broadcaster to influence what they were watching. The notion of teleportation was the moment of clarity that changed the course of the company. Within days, Kayvon and Joe had built a new deck and recruited a video engineer. The team raised a round of funding with this new vision—and the rest is history. For Periscope, their epiphany came from analyzing the market, which led to the right question. As I look back, the ambiguity prior to the team’s pivot was a clue that more discussion and circumspection was needed. When the right question was finally asked, everything became illuminated. Whenever I meet with a team that lacks clarity or feels stuck, their breakthrough often comes from a new question or problem to solve rather than a better answer to the original question. When making a decision with limited time and resources (and stress), we’re liable to accept the original premise and charge ahead to create new products or features without even asking questions—or questioning the problem we’re trying to solve in the first place. Whether you’re an author suffering from writer’s block or a start-up team struggling to satisfy its customers, the solution is to change the question you’re asking. If the original question plaguing you is “Why aren’t people signing up for our product?” maybe the better question is “What kinds of people would benefit most from our product?” When you feel lost in ambiguity, ask a different question. A question informs the answer more than we realize. Watch any great journalist at work—like Tom Brokaw or Katie Couric—and you’ll realize that asking great questions is an art in itself. Avoid questions that already include a possible answer to avoid biasing the discussion. If a question is accusatory, it will trigger defensiveness. A rhetorical question won’t get alternative answers. A yes or no question won’t spark discussion beyond its answer. The perfect question is a key to clarity. It unlocks truth and opens minds. It is distilled by having empathy for your customers’ struggles and ignoring sunk costs and past assumptions to get at the root of a problem. When you’re building something new, focus on asking the right questions instead of having the right answers.

Darviridis commented 9 months ago

Sometimes a reset is the only way forward. When all has gone to shit and morale has suffered, how do you recover? Or if your project has failed or you’ve been fired, how do you turn a new leaf? Before cofounding The Muse, a popular New York–based career website, Kathryn Minshew was fired from another company she had founded previously, Pretty Young Professionals. Working at McKinsey in 2010, Minshew and three colleagues, all young women, cofounded Pretty Young Professionals (PYP), a pink, stiletto-clad women’s networking site. In December 2010, Minshew became the first to quit McKinsey, agreeing to run PYP full-time as an unpaid CEO and editor in chief. Describing this decision in 2010, she told Forbes’s Peter Cohen, “There is huge potential in providing useful, empowering content to young professional women. Smart women have a dearth of smart content choices.” This mission acutely foreshadows The Muse, which now serves fifty million users, more than 65 percent of whom are women. But the path to building PYP was fraught with fits and starts and disputes between its cofounders. The multiple redesigns and disagreements about how to run the company left Minshew with a tough choice less than a year after the company’s founding. As she explained in an interview in Entrepreneur magazine: “I spent three weeks alternating between the fetal position and the whiteboard trying to figure out how strongly I wanted to fight for the existing company versus how prepared I was to strike out and do it over.” Ultimately, the two cofounders with the least equity managed to boot Minshew as CEO, using legal threats. “I was blindsided; it came as a total shock,” Minshew recalled. Then, behind Minshew’s back, they relaunched PYP under a new (and still running) label: Levo League. Minshew could’ve wallowed in self-pity and ditched her dream. Instead, she reset: Just months after being nixed, Minshew launched The Daily Muse (now The Muse), a career website run her way. The PYP staff (most of which Minshew hired) joined her, along with one PYP cofounder. The site drew more visitors in its first month than PYP did at its peak. “It was painful, but being forced to start over was a unique sort of gift, because having been through a lot together, the team comes out of it with the confidence that nothing is going to stop us,” Minshew told Entrepreneur. In November 2011, The Muse was accepted into the Y Combinator accelerator program. Today, The Muse is among the most trusted career platforms for millennials, listing jobs and corporate profiles from hundreds of companies like Goldman Sachs, Wells Fargo, Gap, HBO, Condé Nast, and Bloomberg. “My heroes, in real life, tend to be people who either broke through barriers or overcame tremendous obstacles—not only individually, but people who opened up pathways,” Minshew said in Anthropologie’s “Women of Character” feature. She, undoubtedly, is one of those people. Kathryn’s story is a common one. Conflict prompts disappointment, followed by perspective and self-examination, and ultimately another attempt with a renewed sense of purpose. Leading a reset happens in six phases: feeling anger, removing yourself, dissecting the situation, acknowledging your role, drafting your narrative, and then getting back in the game. Feel the Anger If you’re seething with anger and disappointment, let yourself feel it. The emotion is real, and denying it keeps you angry or, even worse, leaks into other parts of your life. Remove Yourself The second phase is giving yourself space to get some perspective. Something went wrong, you’re angry and upset—but you also have one life to live. While you may feel the urge to jump back in and vindicate yourself, your brain—and judgment—will benefit from a context switch first. It can be hard to remove yourself from the situation you’re in, but when you take a time-out—perhaps a week abroad or simply a trip to the beach—you’ll wonder how you could have recovered without it. You’re free and you’re alive—don’t forget it. Dissect the Situation After the anger has subsided and you’ve put some distance between you and the instigating incident, it is time to dissect the situation with a sound mind and some perspective. What went down? Did you see it coming? Why or why not? Play back lines in your head: Who said what, and why? What other external factors were at play? Also ask your partner, spouse, or close friends for their perspective. Were they surprised? What do they think happened? This is the learning phase. You’re not trying to assign blame: You’re just trying to understand what happened. Think of yourself as an impartial detective pulling apart a crime scene to gather as much data as possible without coming to a conclusion too quickly. Acknowledge Your Role Once you have a full understanding of the situation, own your role in it. What decisions did you make that were, in retrospect, wrong? What did you fail to communicate? Who and what did you underestimate or overestimate? What would you do differently? Make sure the “if-onlys” go both ways—you should not only identify the external factors and people who would have prevented the problem, “if only they had done something different,” but also apply the same scrutiny to yourself: “If only I had . . .” As you absorb the lessons, you optimize your future potential. It is also healthy to close the loop with people you may have wronged. Reach out to colleagues, clients, or investors you may have wounded and share your perspective. If necessary, apologize. This closure is

as much for you as it is for them. You can wipe your slate

clean only when you’ve been held accountable and address loose ends. Without such closure, you will continue to use your psychic energy to process the guilt or anger. Draft Your Narrative Now it’s time to connect your experience with your plans for the future. Start by writing out what happened and what you learned. This narrative is less about crafting your story and more about spending the time to synthesize what happened, what you’ve learned from it, and what you hope to do next. This story line is what you will tell yourself as the next project begins. You’ll also end up sharing a rendition of it with others for years to come as you put your past into context with your future endeavors. Sharing your recovery and the lessons you learned turns failures into opportunities and inspires others while gaining their trust and respect. I always encourage people who are switching careers or dealing with a major setback to draft a blog post or long letter, even if they don’t publish or send it. Get Back in the Game With hard lessons learned and a clear narrative, you need to throw yourself back into action. Remember that you’ll need to take a few steps back to head in a new direction. Sometimes this means reducing the scope of your aspirations, but it is progress nonetheless. So long as you are advancing your genuine interests and feeling utilized, you’re headed in the right direction. When you find your mind drifting to the past and questioning yourself, focus on the fact that you are now more qualified to weath erwhat’s ahead. Every storm better prepares us for the next. Trying again after getting beaten down is never easy—but the important things never are. You will recover and thrive. Do it one step at a time.

Playing the long game requires moves that don’t map to traditional measures of productivity. The human mind is remarkably shortsighted. We’re very good at recognizing cause and effect and projecting the short-term implications of our actions. But we struggle when it comes to chain reactions and laying the groundwork for future opportunities. It takes an entirely different set of measures to engage and endure the long game. The long game requires us to sometimes break the rules of productivity. For instance, do you take meetings that could only yield a possible transaction in the near term, or are you seeking to build relationships that may yield collaborations many years from now? Are you willing to spend time just brainstorming for the sake of brainstorming, even when you’re busy? Do you make time investments only with people who can give you something you want right now, or are you willing to invest in people in whom you believe, even if you think their next project is more likely to succeed than their current one? While many people claim to value long- term moves, few people have the patience. Curiosity is the fuel you need to play the long game. When you’re genuinely curious about something, you’re less likely to measure productivity in traditional ways. Instead, you’re content being in the muck and gain satisfaction from learning something new, not just ticking off to-do items. Rather than seeking a positive outcome, you’re exploring all options to satiate your own interests. The greatest venture investors I know are insanely curious. For instance, over the years that I have known Bill Gurley, the famed investor behind OpenTable, Stitch Fix, Zillow, and Uber, I have always been struck by how deep he’ll explore an interest despite a packed schedule. Whether learning about the transportation industry or oncology and urgent health care, Bill will explore an interest for many months or years without concern for when—or even if—the right investment opportunity will present itself. He’s not racing toward a transaction against a clock; he’s digging to learn. The long game gets even harder when others get involved. If you’re really playing the long game and turning down immediate opportunities, people will probably start scratching their heads. The seeds you’re planting —long-term relationships, curiosity-driven explorations, thought experiments—are less likely to be supported by others both socially and financially. In a talk he gave at the Aspen Institute in 2009, Amazon founder Jeff Bezos, legendary for his long-term vision, reiterated this point. “Invention requires a long-term willingness to be misunderstood,” he said. “When you do something that you genuinely believe in, that you have conviction about, for a long period of time, well-meaning people may criticize that effort.” To sustain yourself over this time, you can’t look for accolades, and you can’t rely on being understood. Playing the long game is a test of your fortitude, your ability to persevere, and just how genuine your interests are.

D Strategy is nourished by patience. There are so many people in the world with ideas to transform industries and build iconic brands. But very few people can stay loyal to a strategy long enough for their vision to materialize. While a great strategy can be conceived quite quickly in a vacuum void of time and reality, it can be executed only over a long period of iteration, agony, and harsh reality (the messy middle!). To allow strategy to unfold, you need to refactor your own expectations and measures of progress while developing a culture and structure that ensures your team has the patience to stick it out with you. Companies are as impatient as people, if not more so. If your project is under the gaze of a large organization, often measured by its quarterly results, it is often exceptionally hard to get the necessary time and space for your bold strategy to materialize. Teams must therefore build systems to nourish patience, culturally or structurally, and you must be willing to defend your long game. CULTURAL SYSTEMS FOR PATIENCE uring Amazon’s first year as a public company in 1997, Jeff Bezos sent a now famous letter to his investors. He started it by outlining his strategy to become a market leader. “Because of our emphasis on the long term,” he wrote, “we may make decisions and weigh tradeoffs differently than some companies. Accordingly, we want to share with you our fundamental management and decision-making approach so that you, our shareholders, may confirm that it is consistent with your investment philosophy.” Bezos then proceeded to outline for his investors and, more important, for his team exactly what this meant. This is a helpful reminder of how a company culture can be crafted to nourish patience with strategy. We will continue to focus relentlessly on our customers. We will continue to make investment decisions in light of long-term market leadership considerations rather than short-term profitability considerations or short-term Wall Street reactions. We will continue to measure our programs and the effectiveness of our investments analytically, to jettison those that do not provide acceptable returns, and to step up our investment in those that work best. We will continue to learn from both our successes and our failures. We will make bold rather than timid investment decisions where we see a sufficient probability of gaining market leadership advantages. Some of these investments will pay off, others will not, and we will have learned another valuable lesson in either case. When forced to choose between optimizing the appearance of our GAAP accounting and maximizing the present value of future cash flows, we’ll take the cash flows. We will share our strategic thought processes with you when we make bold choices (to the extent competitive pressures allow), so that you may evaluate for yourselves whether we are making rational long-term leadership investments. We will work hard to spend wisely and maintain our lean culture. We understand the importance of continually reinforcing a cost-conscious culture, particularly in a business incurring net losses. We will balance our focus on growth with emphasis on long-term profitability and capital management. At this stage, we choose to prioritize growth because we believe that scale is central to achieving the potential of our business model. We will continue to focus on hiring and retaining versatile and talented employees, and continue to weight their compensation to stock options rather than cash. We know our success will be largely affected by our ability to attract and retain a motivated employee base, each of whom must think like, and therefore must actually be, an owner. We aren’t so bold as to claim that the above is the “right” investment philosophy, but it’s ours, and we would be remiss if we weren’t clear in the approach we have taken and will continue to take. Bezos has included this letter as an appendix to every Amazon shareholder letter he has published since. He clearly wants to reiterate these principles to every investor and employee every chance he can. Another story about Bezos addressing his team in the early Amazon days, following an incredible quarter of performance, sticks with me. Bezos congratulated his team but then reminded them, “If we have a good quarter, it is because of the work we did three, four, five years ago, not the work we did this quarter.” There is a huge lag between great innovations and results. A new program takes a ton of refinement and optimization, as well as the natural passage of time, to spread and perform. Amazon is perhaps the greatest corporate example of patiently executing a strategy over time. My friends at Amazon talk about how Bezos’s external emphasis on long-term thinking constantly reinforces the value of taking risk and pursuing a long-term strategy within the company. When something fails, like Amazon’s phone that barely lasted a year, Bezos makes it clear that he anticipates even more—and greater—failures ahead if the company is innovating enough. And when a new technology emerges, like Alexa, the company’s voice-driven user interface, it is allowed to evolve without being immediately subjected to measures of profit or utilization. So long as the team has conviction for the long-term strategy, judgment is kept in check. By nourishing strategy and patience throughout S Amazon’s culture, Bezos has overhauled the natural human desires for immediate returns and near-term measures of progress. STRUCTURAL SYSTEMS FOR PATIENCE ome companies, like Google, nourish patience with strategy structurally. As a large company generating more than 90 percent of its revenue from advertising, the company has taken drastic steps to separate bold new initiatives from the gravity of its core business. The historic decision in 2015 to rename the entire company “Alphabet” and treat Google itself as just one of many companies in the holding company was an effort to structurally protect new projects with longtime horizons as independent companies outside of Google’s operating business. As a result, you get companies like Waymo pursuing autonomous- vehicle technology. These portfolio companies are liberated from the need to add near-term value and rationalize their existence on a quarterly basis. On a smaller scale, some companies will separate certain teams in terms of who they report to, where they are physically located, and how they are measured to provide protection against the quarterly drive for profits and shorter-term impact. Designing the structure of a project or company to foster patience is ultimately an effort to limit our natural tendency to obsess over measuring progress with traditional near-term measures. Patience doesn’t mean tolerating inaction or slower progress: It means allowing alternative forms of measuring the impact of action. Aaron Levie, founder and CEO of enterprise cloud-storage provider Box, said it best on Twitter: “Startups win by being impatient over a long period of time.” Success stories downplay the role of patience. They artificially depict the speed of progress, and believing them makes you liable to give up sooner. For instance, many people look at online streaming service Netflix as an obvious replacement to Blockbuster’s video and DVD rentals, but this seemingly simple process of moving from one trend to the other spanned a decade of persistent execution of a simple strategy: Move the video rental experience online and out of physical stores. The first part of this strategy was to move customers from in-store rentals to DVD-by-mail rentals. After all, in the late 1990s, streaming two- hour-long videos online was a technical nightmare for both providers and consumers. Only with the advent of faster and cheaper broadband did Netflix’s digital subscription service become a viable option on a mass scale. For many years, Netflix was questioned and even mocked by industry analysts. Netflix CEO Reed Hastings even approached Blockbuster CEO John Antioco in 2000, when the company was still focused on DVDs by mail, and reportedly offered to sell him the company for $50 million. According to Variety, Antioco thought Netflix was “a very small niche business” and declined the opportunity. Blockbuster went bankrupt in 2010 and, as I write this, Netflix is now a $150 billion market-cap company. It took nearly two decades for Netflix’s strategy to play out and the tide to turn. Seemingly quick wins have deep roots. You need to set up and provide measures for your team to help them endure long periods of doubt, ambiguity, and being misunderstood. Being able to extend your team’s hunger and drive over a long period of time is the ultimate form of patience. What you give up in near-term measures of productivity must be made up for with an increased near-term focus. Patty Jenkins, director of the recent reboot of Wonder Woman, remarked in a Business Insider interview on the necessity of a tight focus over a multiyear project. “Longevity of focus is, I think, the hardest part,” she said. “To have a vision and then try to hold that vision and not have it change when a million elements around it change every day—like what a shot turned out like . . . or how the story changes subtly—the challenge is trying to hold on to the center.” However you decide to hack the structure of your team to allow for a long-term execution of strategy, you must hold on to the key elements of your vision. THE PERSONAL PURSUIT FOR PATIENCE D A espite how much we intellectually understand the importance of pursuing a strategy with patience, few of us are willing to pay the price of patience. In negotiations, we still seek to optimize for the fastest reward with the least near-term risk. We get impatient with an investment thesis during day-to-day market fluctuations, even if we structurally believe in it over the long term. And we’ll spend a year working on a project and then begin to question it just weeks after launch rather than allow enough time to pass for an idea to become relevant or a brand to become recognizable. Sadly, most people are not patient enough to reap the fruits of their own labor. Great teams gain their strength and resilience while toiling their way through the valleys, not just from relishing the view from the peaks. And yet start-ups lose people when the tough challenges come up. These same challenges will ultimately distinguish you and become your moat of defensibility—if and when they are conquered. Sustained patience and persistence can be such an amazing competitive advantage. Progress takes time, even when you have the very best strategy, people, and resources at your disposal. To foster patience for yourself and those you lead, pick a speed that will get you there, and then pace yourself. Celebrate persistence over time as much as the occasional short-term wins you have along the way. Craft a culture in your project or team that values adherence to a vision and continual progress more than traditional measures of productivity. Establish a structure that allows teams to pursue long-term projects beyond the gravity of day-to-day operations. And remember just how rare it is to stick to a strategy over the long term. This competitive advantage is available to any team, big or small, that is patient enough to stay focused, stick together, and move forward. THE EASY PATH WILL ONLY TAKE YOU TO A CROWDED PLACE s you make decisions with long-term impact, such as selecting the technologies you will use in building your product, keep in mind that whatever is easily accessible to you is just as accessible to others. When I find myself debating a road map with a product team at Adobe, or making decisions about the technical architecture of a product, there is often an “easy option” that provides most of the desired functionality and a “best option” that is inevitably a step function more difficult and costly to achieve. I always prompt the questions: If we take the easy option, how quickly will our competitors be able to catch up? Is this an opportunity for us to make an investment that others cannot make to truly separate ourselves from the rest? If you want to be the industry leader, sometimes you need to take the difficult path. Be wary of the path of least resistance. It may look compelling in the short term but often proves less differentiating and defensible in the long term. Shortcuts tend to be less gratifying over time. The long game is the most difficult one to play and the most bountiful one to win.

Break the long game down into chapters. Most teams just focus on shipping a minimum viable product (MVP). But cofounder and CEO of Pinterest Ben Silberman has been comfortable being underestimated and flying under the radar in an industry where most people judge companies by their latest headlines, flashy keynotes, and the flaunting of their progress. When it came to activating the revenue-generating parts of his business, Ben was also exceptionally (and, for some investors, excruciatingly) patient in waiting for his product and team to be ready. Ben’s patience and discipline come from adopting an atypical timescale compared to the rest of the industry. “Silicon Valley—and the technology industry as a whole—has such a compressed time- scale relative to what I grew up with,” Ben explained to me. “I grew up in a family of doctors where you take seven to twelve years of your life to learn the craft, and then you find yourself as the most junior doctor. So I took this approach to Pinterest. Sure, we value speed, but just because an industry moves fast doesn’t mean we always have to be obsessed with moving fast. I also try to remember, when it comes to best practices for technology companies, that the industry as a whole is still relatively immature. Why conform to the average practices or timescale of the industry? My timescale is longer.” Ben breaks up every period of his company into chapters, each with a beginning, goal, reflection period, and reward. For example, a few years after the business was founded—once Pinterest’s website had a loyal and rapidly growing base of users—the company embarked on a new chapter to “become a mobile service.” At the time, Pinterest was known mostly as a web destination, and Ben believed that the company needed to shift its mind-set to being mobile first. The next chapter at Pinterest was “to become a global service.” Once again, the entire company shifted to make it happen, focusing on certain regions, doing research to develop strategies for serving users in different countries, and making the site available in different languages. And then, a year or so later, the next chapter was “to become a cash- flow positive service,” which meant developing a scalable business model that also enriched the product experience. This chapter ushered in a new set of leaders, partnerships, and changed product priorities. What I like about Ben’s “chapters” approach is that each one applies to everyone in the company and embodies a goal rather than a tactic. Each chapter requires a fresh perspective on the product, renewed empathy with the product’s users, and a candid assessment of the team you have and the team you need. A chapter is a clear goal, underscored by why it is important, and then every team determines its tactics. As a chapter comes to an end, Ben believes teams must be reflective and rewarded. Chapters help break down the long timescale it takes to build something extraordinary. While he doesn’t claim to be an expert, Ben aspires to provide a narrative. “It’s the dream, the drama, the ups and downs—these are the moments and stories that keep us all engaged,” he explained to me. “But you need a mission that can generate the many mini narratives required to carry you through a chapter.” Without a clear mission we’re all liable to get lost.

Darviridis commented 9 months ago

Just stay alive long enough to become an expert. The established paths, tactics, and assumptions relied upon by experts become antiquated. And the more expertise you have, the harder it can be to deviate from established norms. This strong sense of muscle memory held by today’s industry leaders provides an opportunity for you to jump in. The best way for a start-up to “disrupt” an industry is to be a thesis-driven outsider—someone who hasn’t been jaded by the industry but has a strong opinion for what should change. You then just have to stay alive long enough to become an expert so you can compete with the different skills and practices you bring. Some call this “faking it till you make it,” but I think it’s just burgeoning a new path to solve a problem in hopes that it becomes the preferred path. Companies like Airbnb, Uber, and others have done just this. Their founders were outsiders but had a strong opinion or vision about what should change. They then stayed alive long enough to become experts and compete with better technology, a superior path to market, and a lower cost structure. Joe Gebbia, cofounder of Airbnb, knew very little about the hospitality industry when he started the company. “I was so naive. On a scale from one to ten on how prepared I was . . . I was at a three,” he recalls. Joe and his team had the gall to start, but then it took years—and multiple attempts— for them to develop the model that ended up growing into the success we know today. But staying alive isn’t easy. The government’s outdated regulations may try to kill you. Years of anonymity may try to kill you. Insufficient technical skills could make it an uphill battle to survive. When you’re an industry outsider, resiliency is your most critical trait. You and your team need to understand when expertise is an advantage and when it is a disadvantage. This all boils down to the industry norms you’re calling into question and whether or not key dynamics have turned such norms upside down. Rather than believe you can just “do it better” than your incumbents, anchor your thesis on what you believe everyone else is wrong about. More important, your team must value the benefits from sticking together long enough to ramp up expertise, gain velocity, and allow a long-term thesis to play out. As I think back to Behance’s early days, it is striking how underqualified we were. We were all aligned when it came to a mission and what we thought should change in the creative industry, but none of us were creative-industry veterans. We also lacked experiences building online applications at scale. You could argue we succeeded in building Behance into a massive platform despite, not because of, these setbacks. But there were some common practices among the incumbents at the time that ran counter to our ill-informed thesis. For example, most online art showcases at the time, like DeviantArt, Myspace, and Saatchi’s digital community, simply offered online profiles with a collection of images. At the time, this is what the creative web was: lots of images and very little structure. The conventional wisdom was that the more images, the more page views, the more revenue. In contrast, the first version of Behance structured an online portfolio as a series of “projects,” each with its own sequence of images, text, and any other form of media and organized information that would help tell the story behind the work. While our competitors attempted to be online galleries with collections of images, we were trying to help creative professionals tell a series of individual stories about their portfolio of work. Sounds great, but the consequence of this approach was that it was more time-consuming to add an image to Behance than other online portfolio sites. As a result, our user base was low at the start before creatives recognized the benefit the extra effort would bring. If we had known better, we probably would have played it safe. Fortunately, we didn’t know any better, and Behance became known as the more professional and organized platform to showcase and discover creative work. Our inexperienced team stuck together long enough to see our assumptions and plans materialize. In times of extreme uncertainty about the months ahead, we would only question our conviction for the problem and the desired “end state” we wanted to make happen. The long-term conviction never dissipated. We had some near-death experiences that made us smarter and, more important, brought us closer together. Of the first dozen or so people on our team, ten of us were still working together seven years later. The degree of loyalty, tolerance, patience, and shared commitment to a mission was admittedly our team’s only advantage executing in a space that we knew very little about. Cofounder of project management software company Basecamp, Jason Fried, makes the point that the best start-ups are really just “stay-ups.” As he explains it, “Outlasting is one of the best competitive moves you can ever make.”

Do the work regardless of whose work it is. So much of excellence is about just doing the work—even when it’s not yours to do. In big companies, people have a tendency to complain about a strategy they disagree with or a product’s shortcomings instead of their own. In small companies and for freelancers, the tendency is to blame clients or circumstances. So much energy goes into directing blame and expressing disappointment rather than just taking initiative to tackle what you’re criticizing. Everyone has an opinion, but few people are willing to do something about it—especially if it falls outside of their formal job description. Surprising things happen when people take steps beyond their day-to-day role on their own volition. Think your team’s marketing is horrible? Then draft it out, put together a presentation, and share it yourself. Have an insight for how to improve another colleague’s product? Do it yourself, even if someone else ultimately gets the credit (attribution has a way of finding its way over time). Across so many teams I’ve worked with, I’ve marveled at just how quickly an idea takes hold when someone proactively does the underlying work no one else clearly owned. There is rarely a scarcity of process or ideas but there is often a scarcity of people willing to work outside the lines. Those who take initiative to contribute when it wasn’t their job become the leadership team of the newest stuff. There’s a reason so few people do hard work beyond their job description: It’s hard work. You run the risk of expending energy or falling behind in other parts of your life, but these are the costs of playing at the frontier and having the opportunity to lead something new. You’re either a cog in the system or a designer of new and better systems. Of course, if you aspire to transform your industry and leave a valuable mark in your world, you’ll need to challenge every system you find yourself confined by. When you see something wrong, take the initiative to fix it. James Murphy, the founder and front man of LCD Soundsystem, said it well: “The best way to complain is to make things.” When you find yourself frustrated or critical, channel that energy into persistent creation. If it’s not your job, pursue it anyway. Do research, run tests, or draft white papers and presentations to prove your position, even if it’s on your own time. It’ll give you a sense of satisfaction that no amount of preordained tasks will. A shared trait among entrepreneurs and innovators within big companies is defying prescribed roles. The future is drafted by people doing work they don’t have to do. You need to be one of those people—and hire them, too. There is too much wondering and talking, and too little doing. So don’t talk: do. Care indiscriminately. If you’re willing to actually do the work, you’ll have more influence than those who simply do their jobs.

T OPTIMIZE he messy middle isn’t just about enduring the inevitable dips and near disasters. It’s also about leveraging the “highs” of the journey to build momentum and identify and capitalize on whatever seems to be working. If you endure the harsh lessons of the valley, they will help you find the peaks. When something actually works—a new work habit improves your productivity, a key decision improves your team, or a tweak to your product delights your customers—you need to tenaciously evaluate it. Why did that work? How do you do it again? How do you spread it to your team? These positive peaks in the middle of your journey are rarely planned. Planning happens in a vacuum, void of real-world frictions like timing and people. The more you’re trailblazing, the harder it is to anticipate the impact of what you try. Inconsequential changes will prove to be profoundly important while thoroughly deliberated decisions will prove insignificant. You need to be open to surprises, insanely curious about why things happen, and optimize the hell out of everything that gets traction. To make great work tomorrow, you need to have a persistent commitment to outperform today. Every aspect of your product should be far better. Your team should be more capable. The way you market and describe your work should be more compelling. Your work habits and processes should be more efficient. You should be proud of what you’ve accomplished, but never satisfied. Optimization stems from the conviction that you can do better. It’s less about fixing what’s broken and more about improving what works. Look at how Google and other modern web companies pioneered optimization of their products through A/B testing. This is a process by which any webpage or digital experience is improved by comparing the performance of a change (version B) to the previous version (version A). For example, an ecommerce site might change the color of their Buy button for a certain percentage of their customer traffic. If the new version results in more customers making purchases, then they apply the change throughout. If it fails, they abandon the test and revert to the version without the change. So even when something appears to be working just fine, there’s almost always a way to improve it. A/B testing isn’t just for digital buttons—you can use it to advance all areas of your life, from A/B testing your daily habits to how your team functions. A team might change how and when they meet, or an individual may try using a new tool for a week. If it works, the change is made permanent. If it makes things worse, you simply revert to the previous version. The best optimizers are always trying to figure out why something works. Pinterest’s Ben Silberman describes this process as “always reflecting backward and incorporating forward.” As he explains it, “I actually think you learn a lot more from your successes [than your mistakes]. There are a million reasons why something can fail, but usually very few reasons why something can work. When you want to learn to be a great runner—do you study slow people or fast people? I think taking time to understand why things succeed— whether they are your successes or others—is time well spent . . . you learn the most from things that go really well by asking why. Those are the things you want to understand and do more of.” By getting curious about the things that go well, you discover the strengths that are unique to your team and product. This may sound like an obvious practice, but we rarely take the time to improve what already works. Rather than expending almost all energy on problems and putting out fires, you can increase your velocity by optimizing what is already propelling you forward. Industry incumbents lose their position because their success limits their efforts to optimize. Big companies typically spend their time solving problems and sustaining—rather than improving— whatever it is that made them big. As a result, they enter a steady state that may please shareholders in the near term but naturally antiquates over time. “Good enough” is an open invitation for others to create something better than you’ve created. Optimization is most difficult when you have a reliable route that works. Take driving, for instance: Even when you think you’ve worked out the fastest route from A to B, a local cabdriver will always know a way to get you there faster. When you think you already have the answer, you don’t experiment with other options—if only for the sake of efficiency. The problem with large, well-resourced businesses is that they have a well-defined path for everything—and tons of people employed to keep it clear and wide. The probability of discovering a new detour therefore disintegrates with time, as the known path becomes more established. We navigate most of our lives and businesses with cursory knowledge rather than local knowledge. Only when we stick with and deeply explore one area, whether by choice or by accident, do we learn better routes. The section ahead is about celebrating what is working during the messy middle and then capitalizing on it. At first fixing something that isn’t broken will feel uncomfortable, because doing so often requires breaking it. But optimization is the only path to excellence. A journey’s positive slope, where peaks are incrementally higher, is the result of the repeat cycle of evaluating, deconstructing, and building a better team, product, and self. G OPTIMIZING YOUR TEAM reat teams are more than the assembly of great people. On the contrary, great teams are ultimately grown, not gathered. They’re made through endless iteration of roles, cultures, processes, structures, and tackling toxins whenever they emerge. The only way to build a great team is through endless optimization of how a team works together, and clearing their path to solutions. In an entrepreneurial environment, you must prioritize your team over your goals and tend to your team before your product. If your team is not in a good place or your office culture is lacking, your most valuable resources will not be able to make great products or execute well over time. Your team genuinely needs to be as important to you as what you’re making. I have met many founders who obsess over product and steamroll their team. Most of them have failed. Team comes first.

Darviridis commented 9 months ago

Resourcefulness > Resources As your business grows and your plans become more ambitious, you will want to grow your team. When it comes to scaling, the easiest path most leaders default to is to hire. More heads, more hands, more work done. But the best managers know that growing the team is not always the answer. Too many teams hire when they should be optimizing the people they’ve already got. You can always get more resources, but resourcefulness is a competitive advantage. Resources become depleted. Resourcefulness does not. I’ve had experiences on both ends of the spectrum. Bootstrapping a team for five years before raising capital forced me to scale by increasing productivity—even when hiring more people was the right answer. On the other hand, hiring more people was the default for scaling capacity in some of the teams I managed later on at Adobe—and it didn’t always work out. I vividly remember the pain I felt in Behance’s early years when we were trying to balance the need to break even with growing the team. Our engineers had a list of people they “absolutely needed” to hire. But so did our designers and our community management and our support teams. It was a struggle to prioritize new hires (not to mention debating rank). Our head of operations at the time, Will Allen, made a practice of pushing teams to change how they worked before resorting to hiring more people who would work the same way. “Refactor, refactor, then hire,” he’d say. Teams would come into meetings with a list of positions they wanted to hire for but leave the meeting with a list of process improvements they could make with their existing team. Before adding more people to a team, optimize how the team works together. Are there better tools that could be adopted? Can some of the work be automated or outsourced? Are there time-consuming processes that can be killed? Looking back, I am grateful for the years we didn’t have resources. The human resourcefulness that resulted made our team smarter. Every time Will and I ran through this exercise with teams, we would uncover serious inefficiencies and exciting opportunities to boost productivity. We became more efficient before we became bigger. As a by- product of this smooth, satisfying work ethic, we were also able to attract and retain more qualified people. Efficient people want to work in an efficient environment. Resourcefulness also makes you more creative. Any good designer will tell you that creative constraints help the idea-generation process. With fewer resources and options, you become more creative with what you have. One of the best examples of this is Skybox, a company that wanted to drastically reduce the costs of global imaging and other satellite-driven services by creating a cheaper satellite. Prior to Skybox, satellites had cost hundreds of millions (if not billions) of dollars to build, launch, and manage. As a constraint, four Stanford graduate students attempted to build a satellite with off-the-shelf parts. Their first satellite, the SkySat-1, was launched in 2013 and reportedly cost between $2 to $5 million. Their success, largely a product of their self-imposed constraints, ultimately led to their acquisition by Google in 2014 for $500 million. Nothing disrupts resourcefulness more than a sudden infusion of resources. The common debate in the early-stage investor community is how much money is too much money at each stage of a business. This is because there are some serious hidden costs that come along with raising capital. Jessica Livingston, cofounder of Y Combinator, one of the world’s most well-known incubators and start-up investors, talked about the perils of raising too much money too quickly during a talk at one of their annual summits: I’ve seen many startups shift from doing more with less to doing less with more once they’ve raised funding. It’s easy to think money can buy your way out of problems. Don’t like sales and calling users? Hire a salesperson. No one’s using your product? It must be because people don’t know about it—hire an expensive PR firm to get the word out. Those are both not merely lazy, but the wrong thing for a startup to do. . . . When you don’t have enough money, circumstances force you to be virtuous. Once you’ve raised a lot, you have to force yourself to be virtuous. The business of innovation is about a team’s resourcefulness, not just resources. The media’s celebration of financing obscures this fact. The constraints of early-stage business building pave the way for solid operations, healthy margins, and a self-awareness that big companies (and well-funded start-ups) often fail to achieve. These lessons are hard to gain any other way. One of the risks of raising money too early is becoming incentivized to do something you don’t love, and that you don’t truly believe in. Just as you don’t want to have children and commit to being parents together on your first date, wait until you’re committed. Work with a project long enough to fall in love with it, constraints and all, before raising money. You must love your work to survive the journey from start to finish. Resources come and go, but resourcefulness is a muscle that kicks in throughout the life cycle of any business. Without it, capital cannot be used efficiently. Focus on building your team’s resourcefulness.

I Initiative > Experience As you assemble your team, look for people with excitement about the idea, ability to contribute right away, and the potential to learn. What your team lacks in experience they can make up for with initiative. One common principle successful founders swear by is hiring for initiative over experience. It is tempting to be a résumé snob and favor people with industry pedigree, but the unique chemistry of an early-stage venture thrives from a team with hustle and a willingness to learn anything and apply it quickly. DOES INITIATIVE REALLY TRUMP EXPERIENCE? nexperienced yet smart people with initiative will almost always exceed your expectations. But when you’re super experienced, it is harder to bypass assumptions and learn new things. Instead of helping reframe the question and finding new solutions, experts try to use the same answer that worked last time. But in a team that has been gathered together because of their initiative rather than experience, you are fueled by curiosity. A lack of mastery is usually accompanied by the lack of conventional wisdom, which helps you think differently. When you do hire experts, make sure their motivation is more a product of their desire to learn than their desire to provide the fastest answers. Initiative is contagious, expertise is not. For example, one of my favorite junior hires during my days leading Behance was Malcolm Jones. At first, Malcolm became known across the team for his deep laugh, P incredibly wide and constant smile, and can-do attitude. He had only a small amount of engineering experience before he joined us, but the team fell for him after his very first interview. Malcolm joined us as the third member of our dev-ops team, which is a group of engineers dedicated to the infrastructure, stability, and security of Behance’s platform. The dev-ops team is at the front line of every nightmare situation: spam problems, security breaches, latency in the speed of millions of portfolios loading for millions of visitors every day, and, when the site goes down, the dev-ops team diagnoses the problem and fixes it. Putting out fires all day—and trying to make the company flame retardant—is a stressful job, compounded by the constant battery of questions and concerns coming from all corners. On paper, Malcolm wasn’t the perfect fit for the job based on his past experience. But his level of enthusiasm and willingness to take on any responsibility and master it helped him not only succeed but also elevate the dev-ops culture more broadly. Malcolm transformed the team and became a leader we all admired. Skills may be shared, but sheer initiative (and the energy and enthusiasm that comes along with it) helps the culture and spreads like wildfire—the good kind of fire. HOW DO YOU HIRE FOR INITIATIVE? ast initiative is the best indicator of future initiative. Look beyond the formal résumé and ask candidates about their interests and what they have done to pursue them. It doesn’t matter what the interests are—bonsai cultivation, writing poetry, whatever! Instead, gauge whether the candidate has a history of being proactive in advancing their interests. Initiative comes from obsession. The more infatuated you are with something, the more likely you are to know (or want to find out) more about it. The greatest disruptions of industries are facilitated by relative outsiders, obsessed with the industry, who find a way to survive long enough to become an expert and then leverage new techniques to change the game. While expertise qualifies you, obsession mobilizes you in a way that runs circles around the experts.

Diversity drives differentiation. Your product’s unique attributes distinguish you from the competition. These attributes are conceived through clashes of opinion and methods of thinking that diverge from the norm. As every market naturally regresses to the mean, averaging out until it becomes a set of widely established best practices, the best way to drive and sustain differentiation is to diversify your team. The greatest teams I have met over the years are composed of extraordinarily different extraordinary people. The more different your team, the more different and innovative your product. Rational thinking is driven by what we’ve seen and done before. It keeps us where we’ve been. But the greatest products that change our lives are made by teams willing to consider old problems in new, seemingly irrational ways. When someone on your team shares an idea or perspective that, at first, seems completely irrational but then gradually becomes the breakthrough solution, you know you’ve got a team of people with enough “difference.” Innovation happens at the edge of reason, and you can’t reach the edge with a team of similar people. The shortcut to differentiation of thought is diversity in the form of different personalities, genders, ethnicities, nationalities, backgrounds, and kinds of education and experience represented at the table to extend the surface area of possible solutions for every problem you face. We spend too much time considering our own creativity and too little effort on setting up a team that allows creativity to take hold. In an interview with John Maeda on his blog, technologist Nicholas Negroponte said it best: “Where do new ideas come from? The answer is simple: differences. Creativity comes from unlikely juxtapositions.” Maeda goes on to say, “It’s a simple idea really. Yet it embodies everything that I believe—that when you have people who come from different backgrounds together, then the outcome is something that is difficult to expect. By all parties involved. And an unexpected outcome lies at the basis of what creativity is all about.” This is the competitive advantage of diversity. A lack of diversity is a classic flaw of many venture capital firms. A 2015 study by venture capital firm Social Capital found that 92 percent of senior investment professionals at top firms were men, and 78 percent of senior investment professionals were white. Such homogeny, coupled with the plague of groupthink, is a major disadvantage when it comes to discovering something at the edge of reason that the world has never seen. This is the same reason I dislike angel groups, which are groups of people who come together to hear start-up pitches, discuss, and invest as a group. What a horrible model. Groups make us too rational, especially when the constituents are too similar. Groups are even more destructive to innovation —and investing in innovation—when they require consensus to proceed. Diversity in gender, race, sexual orientation, and political views are necessary to form a strong team that covers the maximum possible terrain of perspectives, But don’t stop there; consider the other, less obvious factors —like the languages your team speaks. Gabrielle Hogan-Brun is a research fellow in language studies at the University of Bristol and the author of Linguanomics: What Is the Market Potential of Multilingualism? Her main research focus is on multilingualism’s effect on the brain, and a multilingual person’s subsequent effect on teams. She points out how multiple studies have shown that monolingual brains are structured differently to bilingual brains. For example, bilingual brains have a denser left inferior parietal cortex, which is the part of the brain used in abstract thinking, and they also have more gray matter. Having a different lexicon to draw from can also allow your employees to approach problems in slightly different ways. In Quartz, Hogan-Brun provides this example: In the German mind, the English word “put” conjures up different images: “legen” means to lie horizontally, “setzen” to make something sit, and “stellen” to stand something vertically. Each of these meanings automatically gives the German speaker access to new ways of approaching a practical problem. In this way, using different languages in collaboration may lead to new connections being made, especially when dealing with complex tasks. And it’s not all just physiological and teamwork benefits—there are obvious business benefits, too. Hogan-Brun quotes economist Larry Summers in her article in The Conversation, “Why Multilingualism Is Good for Economic Growth”: “If your strategy is to trade only with people that speak English that’s going to be a poor strategy.” Hiring multilingual people also instantly opens up the potential practical reach of your organization twofold. According to research by Bern University, the economic value of Switzerland’s multilingual advantage generates one-tenth of their GDP. Likewise, in another article, Hogan-Brun cites a survey by the Economist that surveyed 572 international company executives, two-thirds of whom said their teams’ potential for innovation was increased by their multiculturalism. Learning a second language is generally always good for your brain, but there are also different types of bilingualism. For example, growing up in a household that speaks a language different from the one you speak at school is very different from learning a second language at that same school; likewise, speaking two languages fluently from birth has a different effect on the brain than moving to a foreign country and becoming fluent in a second language later in life. But no matter the differences, seeking out people who think in different words from your own is a strength. In her essay for Aeon, “The Bilingual Brain: Why One Size Doesn’t Fit All,” Pennsylvania State University’s Angela Grant argues that though some of the biological benefits of bilingualism can sometimes be overemphasized, “it’s worth remembering that regardless of proclaimed cognitive or anatomical advantages, bilinguals have twice as many communities to interact with, cultures to experience, and newspapers to read. And if that isn’t an advantage, what is?” My cofounder for Behance, Matias Corea, is from Barcelona and primarily spoke Spanish until he moved to the United States as a young adult. Others on our early team were also native Spanish or French speakers, so I experienced some of these benefits firsthand. Our design aesthetic, our ability to engage international communities from the very beginning of our business—which made us look bigger than we were—as well as building a rich, multilingual culture all helped make Behance what it is. Though it is tempting to rope in friends and “people like you” during the early stages of ventures, defy the tendency to be lazy and just hire those in your vicinity. The people who are circumstantially in your everyday life are more liable to look like you, think like you, and have similar skill sets as you. Hiring them will feel safe and easy, but it will handicap your efforts to differentiate your product. By surrounding yourself with people who are different from you, your baseline of adaptability is higher than that of teams who look and think the same. A diverse team can tolerate a greater spectrum of options and circumstances by working alongside people who have endured different conditions and experienced a wider range of challenges. How will your product be perceived by different demographics? What cultural tendencies can be leveraged—or sensitivities considered—in your marketing efforts? A diverse team is more likely to come up with the contrarian’s view alongside new perspectives from different vantage points. When you are hiring, identify your unconscious bias. Don’t accept quick conclusions like “not a culture fit” without digging further to understand what, exactly, isn’t a “fit.” It’s helpful to standardize the early part of your hiring process so it is less vulnerable to biases and more about building a pipeline of qualified candidates who deserve serious consideration despite how “familiar” they seem. Set goals and push your team to widely accept them. As you enrich your team with different kinds of people, it will become easier to do so over time. Familiarity breeds acceptance. When you become more accustomed to working with people far younger or older than you, come from different places, speak with different accents, your mind and hiring practices become more open to the possibilities.

Hire people who have endured adversity. Diversity includes people’s past experiences, so look to build a team of people who have endured adversity and overcome substantial challenges in their own lives. This will bring strength and tolerance to the team’s DNA. In a conversation with Tristan Walker, CEO and founder of Walker & Company Brands, he talked about the role his upbringing added to the culture of his company. “Courage is our first value. The reason I have courage as a first value is because without courage, you can’t practice any other value consistently. My version of courage is that I grew up in the Jamaica and Flushing, Queens, projects. I saw people get murdered, seeing people get shot. All that stuff. My worst case scenario is going back to that, and I survived it. So people are like, ‘Shit—Tristan’s willing to go to the depths of hell to make this thing survive.’ That’s an inspiring thing. I knew what it took to actually get out of that shit, and just having that context made people think about how I make my decisions differently.” When I think about what experiences have matured me the most, they are less university degrees and tenure at esteemed companies and more about the challenges I have faced in my personal life. One of my lifelong challenges has been my relationship with my sister, Julie. She was born with a lack of oxygen reaching her brain, which resulted in severe brain damage at birth. As a child, Julie required years of special education to develop speech and basic social functioning skills. Throughout her childhood, she required a lot of support and patience throughout bouts of behavioral issues. While Julie’s life is complicated to be sure, a childhood with a disabled sibling also comes with a set of complications. On one hand, I felt immeasurable guilt. My possibilities and potential seemed endless compared to Julie’s, and the opportunities and fanfare I received from family always carried a sense of sadness and inequality with it. On the other hand, while I might not like to admit it, I was angry. By no fault of her own, Julie had robbed me of normalcy. Looking back on my childhood and a lifetime of reconciling my relationship with Julie, I recognize how that combustive mixture of guilt and anger motivated me, made me self-reliant, and influenced how I work with and lead others. No doubt, adversity matures you. Traits such as courage, a tolerance for ambiguity, self-reliance, and an urge to prove oneself are more powerful drivers of performance than a couple more years holding a particular job title. Age or accolades have never mattered to me when it comes to hiring or investing in talent: What matters to me is maturity and perspective. As you build your team, seek people who have endured adversity. Ask prospective team members about their most defining challenges. Life matures you a lot faster than time, and a lot of life can happen in a very short amount of time.

Darviridis commented 9 months ago

Seek people with whom discussions evolve by a step function. In a world of pithy sound bites and smooth pitches, aim to work with people who are always building on your ideas and inviting you to build on their own. Your second conversation with a potential hire should feel a lot more interesting than your first. First impressions count for a lot, but if you can’t continually build on that energy, the relationship isn’t likely to have legs beyond the initial spark. I call this kind of fire-starting ability aligned dynamism, which is when ideas vary but energy levels and a value for the mission align; this is the source of the embers that will keep burning long after the initial flint. My friendship with Garrett Camp, the cofounder of StumbleUpon, Uber, and Expa, has always felt this way; same with Ben Silberman before I invested in Pinterest and Kayvon and Joe before I got involved with Periscope. In each of these cases, every conversation felt more interesting than the one before. This stands in stark contrast to most entrepreneurs I meet with, who tend to come at you in a fireball that quickly extinguishes when you meet again or present the tiniest douse of doubt. Whether you’re selecting people to join your founding team or evaluating people you may want to work for or invest in, dynamism is a great litmus test. The best team players will be the ones who are as willing to throw around their own nascent ideas as they are helping build upon others. People who shut down new notions in favor of wanting to advance their own may be heralded as creative firecrackers, but they do not make for good team players in the long term. In the stand-up comedy world, this is known as the “Yes! And . . . ” principle. Charlie Todd, founder of the New York improv comedy group Improv Everywhere, once explained it to me like this: “When you’re vulnerable onstage and throwing out ideas, the last thing you want is to be shut down publicly. Not only does this bring a swift end to the skit, but it’s also devastatingly humiliating. Instead, you should always accept whatever dilemma or circumstances an actor presents to you, and then add to it. You respond with a ‘Yes! And . . .’ rather than a no or some other form of shutting down a conversation.” Of course, to build upon ideas, everyone must understand them. Seek people who make the impossible-to-understand more accessible. One of the greater challenges leaders face on the hiring front is evaluating people with a different technical expertise. For example, how do you evaluate the skills of a cryptocurrency expert or a data scientist if you have no expertise in either one? Sure, you can get third-party opinions from others in the industry, but sometimes recruitment is confidential and your candidates have jobs elsewhere, which restricts how many people you can involve in the recruitment process. But all skills, no matter how scientific, can be explained in layman’s terms—it’s just extremely hard to do it. Despite appearances, simplicity takes deep understanding and synthesis. The greatest thinkers in any field can explain problems and advocate for solutions in clear and simple ways. They use analogies, teach others, and make technical concepts relatable. Genius is making the complicated simple and relatable. Build a team of people dynamic enough to make every conversation a step function that is more interesting than the one before it, and smart enough to make the complicated simple and accessible to everyone.

Darviridis commented 9 months ago

If you avoid folks who are polarizing, you avoid bold outcomes. Creating something from nothing is a contact sport. The endless debates you endure iron out your team’s preconceived notions, and your vehement disagreements force you to explore unpopular options. But debates and disagreements are fruitful only if your colleagues are determined enough to ruthlessly fight it out with you, with one another, and without apathy. The more you challenge one another, the more you will uncover. Not only does a strong culture tolerate some necessary ruckus, it gains its edge from it. People disagree and fight for their beliefs only when they are engaged enough to care. Those who are especially argumentative, opinionated, and polarizing therefore play an important role in your company, as they prevent you from settling for the familiar or easy solution and keep you questioning your norms. So long as they share your mission, these instigators are your greatest protection from groupthink and harmful compromise. Learn to tolerate the people you struggle with. There are many people I have hired over the years whose references included some warnings. While I never compromised on ethics or integrity, I also didn’t aspire to assemble a team of peacemakers. Great creative minds have their demons. After all, if creativity is born from struggle, you must be willing to tolerate the residue. In my experience, some degree of stubbornness and frustration are common attributes of technical geniuses; people who are ahead of their time are intolerant of business practices behind the times. There are a few people I hired over the years at Behance and Adobe who were particularly difficult. But they broke through walls like nobody else. They also pissed off a lot of people, and part of my job was to blunt the pain they inflicted without blunting their impact. Fighting for bold solutions to old problems, especially within a larger company, requires a willingness to defy the typical process. In this way, being a little aggressive is a feature, not a bug. When you find yourself working alongside polarizing people, try to appreciate the role they play and the origin of their struggle. Aspire to turn your disdain into empathy. I’ve always ascribed to the philosophy, often attributed to Carl Jung, that “everything that irritates us about others can lead us to an understanding of ourselves.” Chances are your reaction to others is as much about you as it is about them. The easiest way to deal with people who make you uncomfortable is to find fault with them; judging others is an easier and more cowardly path than reconciling yourself. Instead, to build your tolerance of those you struggle with, ask yourself what it is about their behavior that scares you. How might you possess or fear the same characteristics you are resenting in the other person? If you’re looking for fault or someone to blame, you’re obstructing the lessons you can learn. But if you find ways to accept and empathize with difficult people, your culture will become more tolerant and your product will have more edge. As you’re building or investing in teams, don’t try to keep the chemistry too clean. Teach your team to value conflict and develop a tolerance for passionate and respectful disagreement. When hiring, fight the tendency of your teammates to seek people they “really get along with.” A better hiring criterion is, “Will they challenge us? Are they likely to bring a different point of view?” And then, when sparks start to fly (within healthy boundaries), remind your team that they’re making progress.

Cultivate your team’s immune system, and occasionally suppress it. Like the human body, every team has a natural immune system that serves multiple purposes. The most important part of a team’s immune system helps quickly identify and reject infections. Without a strong response to knowing when something isn’t quite right, small issues can quickly escalate into bigger ones before you have time to snuff them out. In every team I have led over the years, I have noticed that the more attuned and aligned they are, the more quickly a problem rises to the surface. Whether it was a misalignment in priorities, a bad decision, or a bad hire, I was impressed by how quickly it became clear that something was wrong and had to be addressed. But a healthy immune system can also backfire when you are, in fact, trying to change the chemistry of the team. I recall one of the most important hires we ever made at Behance. For years, I had been trying to recruit Will Allen, who had previously run partnerships and helped develop the web offering at TED, to be our chief operating officer. Finally, in late 2011, Will agreed to join us. We were growing fast, and I desperately needed a partner to help manage the operations of our business, including financials, legal work, managing the development schedule, and keeping teams on track. I was certain that Will had the sophistication, values, and management experience to add tremendous value to the company. The team generously welcomed him and Will sprinted out of the gates, joining product reviews, engineering planning meetings, and taking over some functions that I had led for many years. But just a few weeks in, the team’s immune system started to act up. Given his seniority and experience, Will was speaking up and making changes. He started tweaking processes that needed updating and pointing out inefficiencies in our most beloved processes. He changed a dynamic that my design team and I had been accustomed to for years. After just a few weeks, I had a queue of employees requesting time with me to share their concerns. No doubt, Will was a new organ that was required to keep the body alive—but he was also being rejected by a strong and expedient immune system. At first, I started to worry. But as I looked beyond the inflammation Will was causing, I realized that these were merely symptoms of a new and unfamiliar leader digging in, asking questions, and influencing areas that had never been touched. I quickly got that my job was to temporarily suppress the tight-knit team’s immune system. I used the one-on-ones with concerned team members to help them understand the value of the perceived interruptions and, more important, to lower their guard. Immune systems act up in different ways. Sometimes the response is a string of complaints to management. Other times it’s through active disagreement or passive resistance. Or sometimes it comes across as humor. While I was getting my MBA at Harvard Business School, there was a long-standing tradition in every ninety-student section called “sky decks.” At the end of every week, the whole group would come together for announcements, followed by a skit performed by a rotating group of students who poked fun at the week’s events. The skits often involved reenacting an altercation between one of us and a professor, a funny behavior one of us had exhibited during a case discussion, or some other quirk that stood out. It was a good way to make fun of ourselves and let off the steam from a busy week. But a subtler and perhaps subconscious purpose of sky decks was to call out excessive behaviors, like someone talking too much during a case or raising his or her hand too frequently rather than letting other classmates chime in. Since the section had no leader, sky decks served as a natural part of the immune system to foster a healthy and balanced group dynamic. While everyone laughed, everyone also got the message. Sometimes direct confrontation with colleagues is the best path, and other times there are more subtle, comfortable mechanisms to hone a team’s chemistry. The other role of a team’s immune system is to kill off foreign and risky ideas that are liable to take the team off track. Without a strong immune system, deadlines would never be met, and whatever is new and shiny would subsume attention and energy. Typically, the type A “doers” on the team are the powerful antibodies that extinguish new ideas that put time lines and budgets at risk. In contrast, the wide-eyed “dreamers” are the foreign bodies that infect a team with new ideas that challenge the status quo. Most of the time, the immune system (the doers) needs to be strong enough to hold the foreign germs (the dreamers) at bay so we can stay productive and on track. But every now and then, teams need to suppress the immune system so that the dreamers—or any new leader with new ideas —can give the team an organ transplant in the form of fresh ideas, and fundamentally change a process or a product. Much like the Behance team initially struggled with Will, the new organ. When building a team, hire both doers and dreamers in relatively equal proportions. You also need to empower them at the right times. During day- to-day operations, doers must be positioned to question new ideas and keep creative whims in check to ensure progress on the biggest ideas that will make the greatest impact. But when a new problem emerges or a brainstorm begins, doers—and their tendencies—need to be suppressed so the dreamers can do their thing. Of course, many of us have doer and dreamer tendencies that come to the surface at different times. The best teams optimize for a mix of both. If you’re more of a dreamer, be sure to hire doers, even though they may not seem as fun and flexible as you are. They will be the core of your company’s immune system, and without them, you’re liable to get off track. I often see this problem in creative agencies and start-ups founded by visionary types. They seek to hire people like them and believe that a creative company is made up of creative people. On the contrary, successful creative companies have a bold vision and creative leaders who help set it, but are often managed by more pragmatic and progress-oriented doers. You need to hire and empower people who default to the opposite tendency to your own, even if it makes you feel uncomfortable. With every new hire, and in every cycle of innovation and execution, be mindful of your team’s immune system. Let it do its thing, but in times of critical change, take the necessary steps to suppress it.