As a young entrepreneur, I cannot overstate the importance of serendipity. I don’t know whether I’ll ultimately be successful or not, but the success I’ve had so far has been 10 percent inspiration, 90 percent perspiration, and 50 percent surprises. And if you’re saying that this adds up to 150 percent—you’re catching on to my first lesson, which is that it will surprise you how much more it is than you thought: more work, more fun, more pain, more whatever. Your mileage will vary, but here are some of the surprises that I encountered along the way:
1. People love failure. I haven’t failed (yet) as an entrepreneur, but I failed a class in entrepreneurship at Stanford business school because I was too busy working on Piazza. People love the story, and not just for the irony. If you’re relatively smart and you talk about how you failed at something, it makes people think there must be a story there, and it humanizes you. I used to be sheepish about admitting to any failures, but I’m out and proud now. Failed classes, failed marriages—it’s all good.
2. Café > Garage. Naturally introverted and determined to live the Silicon Valley experience to its fullest, I set up in a garage for a while. This turned out to be a bad move for me. Hewlett had Packard, Jobs had Wozniak, Page had Brin, I had … nobody! The good garage stories all have two people, because one person alone in a garage can get kind of Unabombery. On the other hand, when I started working in cafes, I started running into random people. And one of the people I ran into helped me get my first funding and is now on the board of Piazza. Not bad for the cost of a cup of coffee.
3. People will work for free. Despite the ferocious competition for talent in Silicon Valley that famously drives up compensation levels at established companies, there is also a vast informal economy of passionate, entrepreneurial people who get excited about an idea and want to make an early contribution. They won’t work for free forever (and equity is surely part of the mix), but a few times in the past two years, I’ve pinched myself at the quality of work we got without spending any cash at all.
4. It pays to act dumb. I had always assumed that entrepreneurship required a Steve-Jobsian certainty that you knew how everything was going to work. That’s a myth, and an unfortunate one. For Piazza, at least, the greatest advances have come from my saying to someone—truthfully or not—“I don’t know the first thing about X. Teach me.” It’s disarming! And you meet really good people and get really good advice when you “play dumb.” And pretty soon you realize that you actually were kind of dumb, but by that time you’ve learned a ton.
5. Efficiency is not a luxury. When I thought about entrepreneurship, particularly as a person self-funding a company that had no employees, I thought romantically about doing everything myself. I’ll design. I’ll keep the books. I’ll take out the trash. But one thing I learned soon after I had two dimes to rub together was to spend money on my own personal efficiency. For example, the first time I booked a car service instead of renting a car, I closed two important deals balancing my laptop on my knees in the back seat. There’s a reason the division of labor is so successful!
