I talk a lot to people who are deciding between startups and established companies. They’re usually early in their careers and have been exclusively affiliated with well-known schools and companies. As a result, they’re accustomed to praise from family and friends. Going to a startup is scary, as Jessica Livingstone, cofounder of Y Combinator, describes:
Everyone you encounter will have doubts about what you’re doing—investors, potential employees, reporters, your family and friends. What you don’t realize until you start a startup is how much external validation you’ve gotten for the conservative choices you’ve made in the past. You go to college and everyone says, “Great!” Then you graduate get a job at Google and everyone says, “Great!”
But optimizing for external validation is a dangerous trap. You’re fighting over a fixed pie against well-credentialed peers. The most likely outcome is a middle management job where you’ll have little impact and never seriously attempt to realize your ambitions. Peter Thiel’s personal experience illustrates this well:
By graduation, students at Stanford Law and other elite law schools have been racking up credentials and awards for well over a dozen years. The pinnacle of post law school credentialism is landing a Supreme Court clerkship. After graduating from SLS in ’92 and clerking for a year on the 11th Circuit, Peter Thiel was one of the small handful of clerks who made it to the interview stage with two of the Justices. That capstone credential was within reach. Peter was so close to winning that last competition. There was a sense that, if only he’d get the nod, he’d be set for life. But he didn’t.
Years later, after Peter built and sold PayPal, he reconnected with an old friend from SLS. The first thing the friend said was, “So, aren’t you glad you didn’t get that Supreme Court clerkship?” It was a funny question. At the time, it seemed much better to be chosen than not chosen. But there are many reasons to doubt whether winning that last competition would have been so good after all. Probably it would have meant a future of more insane competition. And no PayPal. The pithy, wry version of this is the line about Rhodes Scholars: they all had a great future in their past.
Great institutions can prepare you for great things. Credentials can open doors. But don’t let them become an end in themselves.
People blog for all sorts of reasons. For me, it is mostly about learning. This wasn’t my original intention – it evolved over time. Now I see blogging as part of a continuous learning process:
– Start every morning by skimming through news, blogs, articles, etc. Much of this is tech related. I used to get tech news in the newspaper, then in Google Reader, and now mostly from Twitter. If someone I meet mentions something interesting that was published that I didn’t read, I go back and figure out how I missed it and change who I follow on Twitter so it doesn’t happen again.
– Try to meet with interesting people during the week. The reason being up on tech news is important is so that we can get the most out of the meetings. Often we’ll talk about whatever each of us is working on at the time but it’s also good to have news or blog posts as shared reference points. This makes the meetings more interesting for everyone.
– Try to learn at least one interesting thing each week and then blog about it. Then see how people react in comments, on Twitter etc. I guess some bloggers don’t like comments but for me they are the crucial so that I can get feedback on new hypotheses. Blogging new hypotheses also means a decent portion of your blog posts need to be ignored or ridiculed. Otherwise you are playing it too safe.
Angry Birds was Rovio’s 52nd game. They spent eight years and almost went bankrupt before finally creating their massive hit. Pinterest is one of the fastest growing websites in history, but struggled for a long time. Pinterest’s CEO recently said that they had “catastrophically small numbers” in their first year after launch, and that if he had listened to popular startup advice he probably would have quit.
You tend to hear about startups when they are successful but not when they are struggling. This creates a systematically distorted perception that companies succeed overnight. Almost always, when you learn the backstory, you find that behind every “overnight success” is a story of entrepreneurs toiling away for years, with very few people except themselves and perhaps a few friends, users, and investors supporting them.
Startups are hard, but they can also go from difficult to great incredibly quickly. You just need to survive long enough and keep going so you can create your 52nd game.
“Big timing” is a phrase I’ve heard a lot lately which refers to people who are “higher ranking” acting disrespectfully toward people who are “lower ranking”. Example usage: “so and so VC partner big timed my associate,” meaning they talked down to him/her or didn’t meet with him/her or whatever.
Big timing is a huge mistake. Why? 1) big timers vastly underestimate the degree to which senior people trust their junior people, 2) most non-jerks (no matter how successful) interpret big timing to be an insult to their firm and therefore to their senior people, 3) junior people are often far more active and informed than senior people and therefore great people to spend time with.
It would be great to think that in the startup industry, people would realize that today’s junior person could become “big time” tomorrow, and that you should therefore be meritocratic and respectful to everyone. But that’s not my experience.
My most useful career experience was about eight years ago when I was trying to break into the world of VC-backed startups. I applied to hundreds of jobs: low-level VC roles, startups jobs, even to big tech companies. I got rejected from every single one. Big companies rejected me outright or gave me a courtesy interview before rejecting me. VCs told me they wanted someone with VC experience. Startups at the time were laying people off. The economy was bad (particularly where I was looking – consumer internet) and I had a strange resume (computer programmer, small bootstrapped startups, undergrad and masters studying Philosophy/mathematical logic).
The reason this period was so useful was that it helped me develop a really thick skin. I came to realize that employers weren’t really rejecting me as a person or on my potential – they were rejecting a resume. As it became depersonalized, I became bolder in my tactics. I eventually landed a job at Bessemer (thanks to their willingness to take chances and look beyond resumes), which led to getting my first VC-backed startup funded, and things got better from there.
One of the great things about looking for a job is that your “payoff” is almost always a max function (the best of all attempts), not an average. This is also generally true for raising VC financing, doing bizdev partnerships, hiring programmers, finding good advisors/mentors, even blogging and marketing. I probably got rejected by someone once a day last week alone. In one case a friend who tried to help called me to console me. He seemed surprised when I told him: “no worries – this is a daily occurrence – we’ll just keep trying.” If you aren’t getting rejected on a daily basis, your goals aren’t ambitious enough.