When Do You Stop Being a Startup?
You’ve succeeded in keeping all those balls in the air for a couple of years. Now it’s time for your next trick.
In the early days of starting a company, every entrepreneur is full of confidence and ignorance in equal measure. We’re all whistling in the dark, unsure of what’s ahead and feeling very lonely. And as we search for some signal in the silence, we all end up at the same place: Quora.
Quora was made for, and by, entrepreneurs. Sure, “Data Visualization,” the first category on my homepage, offers about 14,000 followers. But go to “Startups” and there are 3.5 million. “Entrepreneurship”? You’ll find 4.5 million seekers of wisdom. And 27 million curious folks follow “Business”—and so on.
Quora, it seems, is where we entrepreneurs all go to ask: Where am I? And what should I do?
This thirst for guidance, for something to measure against, to know what the heck other people in my shoes did, is what I remember most about my own early days, when I started Iodine five years ago. I went to Quora for wisdom on corporate structure (C corporation or B Corporation or LLC?), fair equity grants, and 83( b) elections, and for advice on how to turn contract workers into full-timers and—once or twice—how to let someone go. Pretty much any question I had someone on Quora had had before. And if the answers didn’t always put me on autopilot, they usually helped me spot the guardrails.
Those days were filled with exuberance and novelty. I was fueled by a fire to get this thing going. I was eager to build a new company, and Quora was going to fill in the blanks in my experience. The energy was everything.
But five years is a long time. Given today’s typical career trajectory, five years could be one or two jobs. And if you’re leading a startup, five years is a curious, in-between place. You’ve survived a purge or two; you could not have made it this far without some amount of success.
Still, you’re not there yet. So you sit, trying, as ever, to make this business a real one. And you’re far enough along that the early enthusiasms have waned and wandered. You’re in a weird place. And now your questions are a bit more existential than those covered in Quora. They’re more like: How do I keep my team motivated and inspired? How do I revive my mission when the dream I sold my team five years ago is, well, five years old? And how do I keep myself confident enough that I inspire every person on my team at every opportunity, as I did that first day?
If you’re a semi-successful startup, you may be able to throw money at the problem, offering swell perks and extra options. But those aren’t real solutions. Those are largely extrinsic motivations, not intrinsic ones: They depend on external factors like wealth and status to keep people engaged. They don’t tap into the core motivations that most humans, particularly those of us drawn to startups, bring to work every day—things like purpose, meaning, mission. We want to be part of something important. We want to be part of a company that is going places. That’s why we went this startup route in the first place.
So what now?
We were fortunate that Iodine was acquired by GoodRx, about three and a half years in. That event reset our clock and work and expectations. It recalibrated our team to be part of something bigger. For us, the acquisition was the perfect wake-up call at the perfect moment. My sense is that every startup, to be successful, must at some point go through a similar recalibration. After all, the game plan in year 7 or 8 is almost never the same as the one on the first day. And if you’re lucky enough to get there, your hard-won wisdom will almost certainly be more valuable and useful than those early dreams. That’s the stuff that people really want to know from Quora.
By the way: For the founders of startups, Quora isn’t just a reference source of knowledge; it’s a model in and of itself. Quora kicked off in 2009. Nearly 10 years later, it’s still a startup, whatever that means. The company hasn’t had that big exit that allows the team to breathe and the founders to rest on their laurels. Here’s hoping it pulls something off soon—and is willing to tell that story to entrepreneurs.