My Anti-Portfolio + Philosophy.

Answering a question I get a lot about my misses.

I have now been in Venture Capital long enough to have missed MANY great investments. I’ll talk about a few here, but before I do I wanted to give new VCs a mental philosophy around missed investments. This isn’t something I stress about too much, and I think a lot of people live with regrets here, so I figured why not write a post.

First I want to articulate how I think about missed opportunities in venture capital:

1. Missing that deal, led me to saying yes to another great deal.

2. It wasn’t a part of my story.

3. If it’s truly a regret, you can always pay a higher price, because the greatest companies compound.

I’ve been investing early for 16+ years now, and I have financially missed some huge opportunities, here are some of the big ones:

1. Ethereum’s initial token auction - 2000 ETH for every Bitcoin you put in. Our entire office, which was full of Bitcoin founders, were buzzing with excitement. I was stubborn and thought that Bitcoin needed to work, before there was some form of alternative. This would have been one of the financially best opportunities to participate in.

2. Lyft, Founded by Logan Green and John Zimmer - In 2011 I met Logan Green at a party. He was then the founder of Zimride. He spent our conversation telling me about this product he was excited to launch called “Lyft” that was a peer to peer ride service. He was raising $1m at a very fair valuation to launch it. I just didn’t push to invest - I believe I could have. I invited him to speak at Boost VC later on, and he crashed my drone. :)

3. Honey, founded by Ryan Hudson and George Ruan - this deal had been referred to me by Brian Armstrong. Honey was a digital coupon company that followed you around the internet giving you deals on everything. The company eventually got bought by Paypal for $4B. My reason for passing was “There is no way that Bitcoin will be incorporated into this yet.”

4. Anduril — There are so many ways we should have invested in Anduril. Boost VC had been investing in VR for ages, so we ran into Palmer Luckey and had been following Palmer for ages. In 2019, I wrote a blog saying that the five prime contractors would become 500 $1B startups. After Anduril’s fundraise at a $1B valuation, I reached out to invest and Palmer said “We would love to have you” and I waited too long to follow up to the follow up.

In this business if you aren’t missing big, you aren’t around in the right markets or around the right founders.

My Dad who has been an investor for 40 years missed Google, Facebook, and Netflix. And I would argue is still the greatest early stage investor of all time.