Learn on someone else’s dime

Fortune favors the prepared mind. – Louis Pasteur

Startups are hard. Long hours, anxiety over whether you’re wasting your time and savings, the rollercoaster of doubt, hope, crushing disappointment, and incredible possibility. The worst of it is feeling that you’re unprepared, that you’re wasting time on technical (or business) decisions that turn out to be wrong – not when there was no way to know, but when someone should have known.

You’re taking a risk, and the stakes are real – time, money, career progress, relationships, experiences. You want to give yourself the best possible chance of success. Part of this is a matter of picking your battles and trying to limit technical risk. Part of it is being prepared, usually by having done something wrong a half dozen times already, and knowing where the pitfalls lie. Part is being able to find great co-founders – both business and technical. Part of it is understanding the industry and market you’re attacking.

Learn on someone else’s dime. Serve your apprenticeship – get the experience, skills, and connections you need to be successful, while building up runway for your eventual leap into the startup world, by working for someone else.

More School

By all means, go to graduate school if you’re passionate about a particular topic, or you’re trying to qualify for a faster green card process. Otherwise, you’re paying (in time, money, and opportunity cost) for some letters after your name that won’t significantly impact your career.


YCombinator, TechStars, Betaspring, etc. are great opportunities for taking a quick run at an idea. But building a company isn’t about taking a quick run – it’s about sticking it out, for years if necessary, to make it happen. Once the summer is over, it’s going to be hard. You’re going to hate it, more often than you’d like. You’re going to feel a lot of pressure to give up and get a safe job with a nice salary.

Knowledge is power – understanding the industry, market, and technology will give you confidence that you’re doing the right thing, or that you can pivot to do something better. Money is power – having cash in the bank will get you through bad times when everything is going against you. Connections are power – having people to call for advice, leads, and, yes, money, will give you a better chance for success.

Incubators try to get you to a baseline on all of these. You get a minimal amount of money, mentors and a community to ask questions of, and connections mediated through the incubator leadership. These are all great, especially the mentoring and connections, and you want to be in a position to take maximum advantage of the opportunity. Even if you make it into the incubator, being a fresh grad without much understanding of “how the system works” (important for knowing which rules to obey and which to break) is going to put you at a huge disadvantage.

So sorry

This post isn’t cool. It isn’t the hip thing to say. A lot of people on teh Internets are going to tell you to ignore the old guy and just jump in – Bill Gates and Mark Zuckerberg dropped out of Harvard, man! If you aren’t throwing away your savings on a crazy idea despite a questionable grasp of how to identify a market, build a usable product, build a team, or make a cold call, then you’re clearly a super-conservative mouth-breathing waste of space!

Or not.

Peter Thiel famously paid twenty kids $100k to drop out of school to pursue startup ideas. If they win, he wins. And if they lose… They’re out of luck, no college diploma, and he’s still a billionaire.

According to Paul Graham, “The total value of the companies we’ve funded is around 10 billion, give or take a few. But just two companies, Dropbox and Airbnb, account for about three quarters of it.” That’s a pretty sharp power function. Go ahead and believe that your idea is going to be in that category, but give it the chance it deserves. Work in a great company that will teach you how to scale. Work at a startup to see how the game is played. Build your connections. Pay off some student loans. For God’s sake, finish school. Then go for it, and don’t give yourself an excuse for why it was ok for you to fail.

2 thoughts on “Learn on someone else’s dime

    • Don’t I know it! (he says while rocking a sniffly baby) Don’t wait too long, or get too comfortable while “getting ready.”

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