I almost made $698,000 — almost. This is how I missed two of the biggest opportunities of my career…
Three years ago, I had the opportunity to be an early investor in two incredible startups: Figure and Anthropic.
I wound up passing on both.
How to Lose $698,000
Today, Figure is valued at $39 billion. Anthropic is valued at a whopping $380 billion.
Both are about 100x higher than when I passed.
At the time, I was writing $5,000 checks (I’ve since doubled that).
Both these opportunities came via syndicates, so I would have lost 20% of any gains. I also would’ve been diluted as they raised more money.
Still, I’d be sitting on paper profits of approximately $698,000 if I’d invested in both. Had I done follow-on, I’d have made even more.
Why I Passed
How did I miss these amazing investments?
Both had valuations far beyond my normal range. My usual entry price is between $10 million and $15 million. Figure was raising at several hundred million. Anthropic was raising at about $4 billion.
Also, both shared very few financials. That’s not uncommon when you’re a small check in a huge round.
Between high entry prices and lack of financials, I decided to pass.
The Importance of Exceptional Founders
What I got wrong was not placing enough weight on the founders’ backgrounds.
Figure founder Brett Adcock previously founded Archer Aviation. Archer is an eVTOL company worth $5 billion on the public markets.
Some people criticize Brett because Archer hasn’t shipped a product yet. But the company is worth billions, completely liquid. Financially, it’s a success.
Dario from Anthropic also had an incredible background. He was Vice President of Research at OpenAI — one of the top executives.
Brett and Dario’s backgrounds alone should have been reason enough to write the checks.
Startups Can Get a Lot Bigger Than You Think
For an investment to make sense for me, it must be able to return at least 300x. I was concerned there wasn’t enough upside with Figure and Anthropic.
But if humanoid robotics works, creating a hundred billion dollar company shouldn’t be a problem. And if you build a highly successful new base model, a trillion dollar company isn’t out of reach.
I underestimated how big these startups could get. Today, they’re well on their way to those lofty valuations.
What I’ll Do Differently Next Time
The next time I see a truly exceptional founder, I’m going to be more flexible on valuation and traction.
Late last year, I paid a higher-than-average price to invest in Cortex AI, which feeds factory data to AI models. The founder, Lucas Ngoo, previously co-founded Carousell, a billion dollar startup backed by Sequoia.
I’ll continue to bend the rules occasionally for the best entrepreneurs. This could help me nail the next Figure or Anthropic.
Wrap-Up
Nobody is in every good deal. Not Sequoia, not Benchmark, nobody.
When we miss great investments, we don’t need to feel bad. But we should take the opportunity to learn.
In the end, everything worked out.
Just a couple of months after I passed on Figure and Anthropic, I invested in a little startup called Micro1. In the last year, they went from $4 million to $200 million ARR.
That’s the beauty of venture capital. You don’t have to be right all the time.
Just once will do.
More on tech:
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Which Accelerators Are Worth Your Time? Here’s How to Find Out.
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