Seven things I learned in venture

Sam Gerstenzang
2 min readMar 4, 2015

--

I left Andreessen Horowitz 5 months ago to join Imgur. Below are seven things I learned in venture that have been useful.

  1. The winners always have something that looks hugely wrong with them. Like spectacularly wrong. That’s why no one else has invested/hired/built this opportunity. But you can. Value strength over lack of weakness.
  2. Venture (and everything else) is a service business. That means you need to sell yourself to your customers (entrepreneurs, potential employees, partners) all day long. Everyone you talk to, especially the people you turn down, should walk away wanting to work with you even more than they did before.
  3. The best way to become quickly knowledgeable is to find the right people and talk to them. Of course, do your homework first. But there isn’t a substitute to finding the three people in the world who know best and triangulating their answers.
  4. Managing a portfolio as a collection of risk-reward ratios leads to superior returns. Make sure to have a mixture of low reward, low risk and high reward, high risk projects at work and in life.
  5. There is no template for success, and no one knows what works. Everyone is winging it, so make sure you take apart advice to understand why it worked once, for that one person, in that one situation.
  6. Big things growing really fast get really big, really fast. Bettings on these things when they seem large but are still growing is a good bet. Counter: make sure you understand why they’re growing, because there is real growth and then there is sugar growth. Sugar growth is fast but stops abruptly.
  7. There is a huge advantage to being right early on. In venture, in each new job and in your career, those attached to winners are associated with success. If you have great investments early, the results can snowball.

Shoutout to Sarah Tavel’s great post on 3 skills you’ll learn from venture. You should read it.

--

--

Sam Gerstenzang

Building @askumbrella. Previously building products, teams, and companies at @sidewalklabs & @imgur, investing at @a16z http://samgerstenzang.com