10 Surprises of a First-Time Entrepreneur


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!

6. Chit-chat is necessary. I am blunt. I am focused. I am efficient. I measure opportunity cost every minute. To this day, “the schmooze” is one of my weakest skills. But I work on it, and it has mattered a lot. My closest advisor wanted me to meet someone who had no connection to anything Piazza does. I put off the meeting because at a busy moment it seemed like random chit-chatting. But the guy turned out to have insights that have been invaluable to us. And also, we’re now married!

7. People want to help. The number of truly helpful people in the world is small, but it’s way bigger than I thought, and it doesn’t take that many. One of our biggest breaks came when a celebrated instructor from Berkeley sent an e-mail to hundreds of people telling them how awesome our product is. He didn’t have to do that, but as Guy Kawasaki would put it, hes a mensch. I always want to find mensches (menschen? Work with me here; I’m Indian)—but I’ve found that the best way is to try to be as helpful as I can to others.

8. Silicon Valley is a state of mind. The nature of our business is such that I’ve traveled to a lot of places in North America that are geographically and culturally distant from here. But everywhere I go, there’s a little bit of Silicon Valley, and people who want to be a part of it. One of our early engineers is actually still a college student, and he hails from a one-stop-light town in the Midwest. But he’s a Valley guy to the core. So I actually flew to Illinois one day to convince his parents that it would be okay for him to take a term off from school and work here. And they were great, too!

9. Myopia > Vertigo. If I had contemplated two years ago all of the things I’d have to do to get Piazza as far as it has come, I would have collapsed into madness like Jimmy Stewart in that Alfred Hitchcock movie. So instead I’ve cultivated and embraced myopia. Every day I try to clear my head of the “big picture” issues and focus on what I can get done today. Now I’m getting to the point where I can think about the very big picture and what I have to do today, while delegating that vertigo-inducing middle area to talented people.

10. Being an introvert can help. I’ve already mentioned that chit-chat doesn’t come naturally to me. Nothing exhausts me like a day spent talking to strangers. But introversion has been an advantage in two ways. First, I was the only person in the world who cared about Piazza for months, and I survived that.  Secondly, when I go out and talk about Piazza, people can tell that I’m not a natural saleswoman, and I’ve heard that my earnestness makes the pitch more effective.

I think Piazza is the only thing in the world I could actually go out and sell. I don’t have kids yet, but I know you’re not supposed to brag about your children no matter how cute and brilliant they are. Starting a company, I’ve had a unique opportunity to be out there talking about something I created that I truly love.

Pooja (Nath) Sankar is the founder and CEO of Piazza, a social platform for students and teachers. Follow @

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13 responses to “10 Surprises of a First-Time Entrepreneur”

  1. John says:

    wow, smart and beautiful. great article. unibomber joke made me laugh.

  2. Great article and very candid. An enjoyable read, thank you for sharing your story and inspiration.

  3. Great post, you hit the nail right on the head with your 10 tips, tip 4 was sweet and funny it pays to act dumb” one thing about being an entrepreneur you do not have to go to school for 4 or 8 years to be successful at it.

    I start in the 6th grade selling candy, it just takes focus and a desire to win great post.

    To The Top

  4. Michael says:

    You’re way too young to have learned all that; it took me 60 years & multiple companies. Excellent advice, yet, I cringed at the nonchalance of failures – especially marriage.

    Best wishes, Mike

  5. Kashif says:

    Great article. Very proud and happy to see someone originally from Bihar make it.

  6. Dr.A.Jagadeesh says:

    Excellent article. Your experience should serve as model for young entrepreneures.

    Dr.A.Jagadeesh Nellore(AP),India
    E-mail: [email protected]

  7. Excellent posting. These are truths that often come from years of experience. Life is often the best teacher. You may be introverted, but you are a very quick learner, and I predict will go far with your business.
    Michael Langhout

  8. bc german says:

    i wod like to know abaut any tips of knowlge