Digests of Jessica Livingston's


Subtle Mid Stage Startup Pitfalls

  • If you find yourself feeling you can relax, that means you’re overlooking something, because the one thing all the most successful founders we’ve funded agree on is that it never gets any easier.

  • The more successful you are, the harder the job gets.

  • When you don’t have enough money, circumstances force you to be virtuous. Once you’ve raised a lot, you have to force yourself to be virtuous.

  • The sooner you acknowledge that growth is flat, for example, the more time you’ll have left to fix it.

  • It’s the idea that as soon as you hire a single mediocre person your startup is in danger of being infested by mediocrity.

  • The most common mistake YC dinner speakers say they’ve made is waiting too long to fire people.

  • They learned how to manage by watching people they were supposedly managing!

  • Another technique that several mentioned was getting together regularly with other CEOs in the same situation to talk about their problems.

  • In the seed round investors are betting on the vision, but in the A round, they need to see results.

  • One simple but effective piece of advice for dealing with investors is one I learned from Ron Conway: over-communicate with your investors and confirm things in writing.

  • Another advantage of being profitable, in addition to making yourself appealing to investors, is that you can walk away from any deal.

  • In fact, in the first year or two, founders should not deal with acquirers, period.

  • Once you let yourself think about the possibility of getting a big chunk of money and not bearing the burden of running a company anymore, you may start to lean toward selling.

  • And be very careful about what you say, both as a company and as individuals, even in what might seem like private conversations.

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