Scott Kupor

Supported by Greenhaven Road Capital, finding value off the beaten path.

Author of the 2019 book, Secrets of Sand Hill Road, Scott Kupor spoke at Berkeley about being a venture capitalist, the two most important things for a VC investment, and the role of luck.

Education. Kupor wanted to be a lawyer until he worked as one. His first summer internship showed that practicing was quite different from studying. He’d seen this before. As an undergraduate he’d transferred from Wharton to Stanford and “The best thing was that at Stanford I was kind of forced to, because of the general curriculum, to do some stuff in other areas. I took a religious studies class and I took some philosophy classes for the first time.”

Kupor, like a lot of young people, overindexed on certain parts of education.

  • Learning is good, to a point, and then doing is better.
  • Focus is good, to a point, and then broadening is better.

Tyler Willis saw this too, noting that he became a wiser person when, “I became a fairly voracious reader. I read a lot of nonfiction to understand different people’s opinions about different things. I read history, biographies, a lot of varied topics.”

Kupor agrees, “If I could do it (school) all over again, the extra hour I’d might have spent at the library invested in relationship development.” School is great for the things you’ll know, the people you’ll meet, and the access you’ll have.

Luck. Kupor was lucky. “The only reason I got introduced to (Marc Andreessen and Ben Horowitz) is because I knew somebody who took a job who said, ‘Hey these are interesting folks, you ought to meet them.'”

How to get an investment from a16z. We’ve covered founders Marc Andreessen and Ben Horowitz quite a bit on the blog but Kupor gives a nice overview. First, entrepreneurs should consider if they want an investment. Money is fungible so what else does a company bring? “There’s a lot of places you can get money (so) at some point you wanna be able to say, ‘Look, I’ve seen the company building process through my own eyes and how I can be valuable to you as a new CEO.'” Contrary to Kupor, David Heinemeier Hansson provides a different perspetive on the value of venture.

If a16z is the right place, entrepreneurs should prepare three things.

  1. The idea maze. Andreessen told Barry Ritholtz that “It’s this incredibly deep and elaborate process of thinking,” and the best entrepreneurs get frustrated with VC’s questions because they’ve already figured that part out.
  2. The market size. “A cardinal mistake is investing in something that turns out to be a good business in a small market.” Another mistake is when “you intuit from your own experiences.” Kupor and co. missed investing in AirBnb’s ‘A’ round because they thought the market was small, college kids on couches.
  3. Customer acquisition costs. “The major conundrum with consumer companies today,” said Kupor. Though fellow a16zer Alex Rampell has spoken at lengths about approaches to this issue.

Intellectual humility. “Your job is to know what’s happening day-to-day in your business…but I think it’s perfectly reasonable to say, ‘I’m not sure if now is the right time to bring on a head of sales or upgrade from my buddy running engineering to someone with more skill in that area.'”

In marketing there’s the expression, half of my marketing is wasteful but I don’t know which half. In decision making there should be an acceptance of the corollary, half of what I know is wrong but I don’t know which half.

No one expects you to know everything, Kupor explains, but you should know the difference between the things you should and don’t.

Thanks for reading.

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