Never underestimate your first idea

Over the last year, I’ve had the chance to sit down with dozens of founders as host of the Masters of Scale podcast. Through these conversations I’ve honed my theories on what allows companies to scale spectacularly, and how these individuals realize their visions.

For this week’s show, I had a very free-flowing conversation with Ev Williams, who founded (in order) Blogger, Twitter and Medium. His career has had such an over-arching impact on how we communicate online that it’s like a history of the entire medium (no pun intended). Any time you share an idea online, chances are Ev helped you express it.

Ev and I have a lot in common. We’re both serial entrepreneurs who’ve paradoxically spent our careers in an almost single-minded pursuit of a single idea. When you look at the companies we’ve founded or invested in, it’s clear that both of us have a fundamental question we’re trying to answer. For Ev, it’s: “How do we connect all the world’s brains into one idea-sharing machine?” For me, it’s: “How do you build social and professional networks that enable us to help each other?”

If you ask this type of sweeping question at the beginning of your career — and if you happen to be riding a wave of massive social and technological change — you’d be surprised by just how long you can keep riding it, without ever getting bored.

If you’re this type of entrepreneur — who’s devoted to a vision and persistent enough to pursue it through multiple companies over the course of a lifetime — I have a few pieces of advice for you, which Ev and I dig into for this week’s episode of Masters of Scale:

1. Bet on the way the world is moving. If you can spot a profound, transformative change that’s happening in the world, bet on it. Play the possibilities forward in your mind, and keep moving along that path. Ev’s first project was a VHS tape that taught people to use the Internet in the early 90s. His first company was Blogger, the tool for self-publishing in the early 2000s. The world wasn’t ready yet for Twitter or Medium — but it would be. The more people came online, and the more accustomed they got to expressing and consuming ideas, the bigger the solution Ev could build.
2. Start from where you are. The challenge of a big, over-arching vision is that it’s hard to know where to start. And your biggest opportunity will change from year to year. Technology changes. Competition changes. You change. My advice: Just start. Find a single unmet need that nudges the world closer to where you believe it’s going. And if you hit a dead end, pivot. Not many people know this, but Twitter was born out of one of Ev’s failed ventures: an early podcasting company called Odeo. Before it even launched, Apple expanded iTunes into podcasts and wiped out their business model. Twitter was conceived at an Odeo hackathon to answer the question: What now?
3. Don’t worry about a wipeout. When you’re riding a wave of massive change, the journey is unpredictable. You may surf gloriously on a seemingly endless swell, or you may end up beached at low tide. That wipeout may only be one chapter in your scale story — and the lessons you learn from failure can help ensure it’s not your last chapter. No one introduces Ev as the founder of Odeo. But Twitter wouldn’t exist if Odeo hadn’t failed. And no one introduces me as the founder of SocialNet. In fact, almost no one’s heard of SocialNet, my first startup. But that failed website taught me how to spot the investment opportunities in Facebook and Airbnb, and how to make LinkedIn a success.
4. Persevere. And position yourself for luck. There’s a myth of entrepreneurship that says successful startups were just in the right place at the right time. Timing is linked to success, no doubt. But passion and persistence are also paths to scale. And when you’re working toward an overarching vision that you personally believe in, this actually gives you the basic ingredients of grit (The awesome psychologist Angela Duckworth explains this in the episode). When Blogger ran out of money, and the rest of his staff left, this is what propelled Ev to continue working on it, alone, in his apartment, with no salary — for two years. His timing was right, but he wouldn’t have succeeded without grit.
5. Don’t derail your own destiny. Our culture lionizes entrepreneurs who navigate daring switchbacks in their career. Steve Jobs was admired not just for Apple, but also his detour to found Pixar. Elon Musk is revered for helming Tesla AND SpaceX. But don’t be distracted by other people’s winding paths. I believe you should celebrate your single-mindedness, and stick to your own overarching idea — for as long as it holds your own fascination. In my experience, that could last your entire career.