Jason Shah

What I Learned About Failing Fast and Winning in the Startup World

Tomorrow will mark one year from my college graduation. The first year after graduating from college is a uniquely challenging time. You are no longer constantly surrounded by friends. You lose control of your schedule to some employer or the demands of your startup. And chances are that you became a ‘regular person’ – even if you’re in the startup world.

Last year I graduated from Harvard with a degree in sociology and computer science. I had built and sold a company during college. I wanted to do it again – at a much bigger scale and it seemed like there was no better time.

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So I moved out to SF in June, set up shop in a sublet in The Sunset, and started coding a product that I thought would be the company that made me. In the year that has followed, I ended up abandoning that idea, moving onto something else that proved to be entirely unprofitable the more it scaled, learned why you should leave your apartment at least once a week, considered doing consulting on the side, and now am a Product Manager at Yammer.

I didn’t expect to be here 12 months ago. If you’re graduating and thinking about joining or launching a startup, there are some non-obvious things to know. Here they are:

Learn the fundamentals, and don’t act like you know them.

In college, mistakes weren’t cumulative. A paper gets a grade. A semester ends. And you graduate. There are fresh starts all the time. But now the game is different. You will accumulate life debt the more you try to bullshit your way through. The embarrassment you think you will experience is nothing compared to outsized intellectual and experiential debt.

If you don’t know how to sell, learn. Now. If you think you can ship buggy code forever, you’re wrong. You need to realize that there is no more “Oh, I’ll learn that later.” Later is now, so stop procrastinating. This means asking questions and letting yourself be wrong until you finally understand. Even when someone says, “So you get how this works, right?”, do not nod your head unless you really truly get it. Because class is over, and now is the time to learn.

Experience really does matter, but only if you pursue it aggressively and build cumulatively.

I used to think everyone who touted the benefits of working at another startup to gain experience was just bullshitting me. I thought they didn’t have the guts to go do their own thing and were just rationalizing cowardice. Since joining Yammer, my understanding of data-driven product decisions, the ins and outs of an acquisition, and how to build a meritocratic culture makes me laugh at my former self. Sure, I could have figured those things along the way; many entrepreneurs do. But learning these sort of things is not binary: it’s not an “either you get it or you don’t.” thing. This learning is cumulative, and no one ever has life or entrepreneurship nailed down pat. It’s not that simple. Instead, you need some mix of good intuition and useful experience to navigate any given situation in the best manner possible. We get better at exercising these skills with more experience, so ensure that you pursue a wide range of experiences aggressively and build on top of previous experiences. When you don’t build on previous experiences, you end up repeating learning processes.

Time is finite, so experiencing the same things means you’re occupying time that could otherwise be useful for learning new things. Failing to learn cumulatively means wasting time. Wasted time means time not spent growing. You need to grow to compete well. Remember to reflect and connect the dots every few months.

Your relationships will determine whether you see some doors open or not, and networks aren’t built overnight.

When you are working somewhere, it becomes easy to forget the rest of the world. When you’re doing your own startup, it seems like any time that is not building or selling is a waste. But you never know where that random connection at a Hackers and Founders lunch may lead. And you never know which other engineer sitting across the room that you might end up starting a company with eight years from now when the Valley is back on the rise yet again.

But then again, you don’t want to waste your time at the wrong events. You will never be perfect at guessing what you should or shouldn’t go to. I would say to do your best to investigate: look at the speakers, look at the guestlist, look at the sponsors. If an event is only sponsored by law firms, run. They are there to develop relationships; you don’t get as much out of them. If it is a panel, check the moderator out on Twitter. Do they ask insightful questions? And what is the title of the event? This actually is half the battle. If it is “Finding a Co-Founder 101” - run. You can get this from blog posts in half the time. If you’re going to hear entrepreneurs speak, to try to get a sense for whether they will be sharing unique personal stories vs. giving condescending boiler-plate advice.

Keep in touch with your college friends, go to events that aren’t bullshit, and keep meeting interesting people.

Do not let your age help you rationalize a lack of responsibility. Make impact always.

You’re an adult. You have been for years, so act like one. If you start saying, “Oh, I’m the youngest guy here. I’ll pay my dues for a couple years, and then they’ll let me be in the driver’s seat.” Wrong. Think like that, and you’ll always be in the backseat. Don’t settle for pushing widgets around or some ridiculous investor terms because you’re “an inexperienced founder.” Listen to what your investors are saying are weaknesses or what your company’s problems are, and solve them. Logic will trump seniority if you’re good at what you do, and conduct yourself respectfully.

Your time is the most abundant that it has ever been. But it’s also the most expensive.

When you’re 21, it feels like you have all the time in the world. I remember thinking “Oh, I have 3 shots at this before I’ll probably be married and can’t roll the dice in the same ways I can now.” Time feels abundant when you’re 20 something. No matter how busy you are, a vast and potentially awesome future lies ahead. But that time is more expensive with every day that passes. You don’t know what will come up that will stop you from starting a company next year. You don’t know whether equity at a startup or perks at a place like Google will make you never want to leave. So treat your time to build a company like the precious asset it is, because starting a company may not always be an option.

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Joining a company and building a company are vastly different. But certain tenets hold true when you’re young and excited to make a mark on the world regardless of where you end up in the startup world. So fail fast and learn with an open mind. It’s a long game. Don’t expect to win after the first inning, but play as if you can.

Thanks to Dan Shipper, Chris McCann, Brandon Liu, Peter Boyce, Vinay Trivedi, Ben Lang, and Jason Freedman for reading drafts of this post and sharing insightful feedback.

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