How I’m Investing at Reasonable Valuations In the Hottest Market Ever

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Investors blow themselves up in red hot markets like today’s. So I’m watching my entry price like a hawk. Here’s what I’m paying so far in 2026…

Inside My Angel Portfolio

Here are my median pre-money valuations, year by year:

2026: $18.5 million

2025: $19.3 million

2024: $8 million

2023: $13 million

2022: $12.5 million

2021: $10 million

My median entry price has jumped substantially over the last two years.

Adjusting for inflation, my $10 million entry price in 2021 would be about $12 million now. So in real terms, my entry price has jumped 50%.

It’s taken all my efforts just to keep it that low!

Tons of pre-seed companies are raising at $50 million, $100 million, or even more. It’s becoming normal.

And just like in 2021, it will not end well.

Paying More, Getting More

My entry price is definitely up. However, the companies I’m investing in today also tend to have more traction.

AI is helping some startups pass $1 million ARR in a few weeks. That didn’t happen in 2021.

When a company has that kind of growth, it’s worth paying more.

Scouring The Planet for Unloved Startups

Startups coming out of top accelerators are priced sky high these days.

I still do those deals when I see something exceptional. But increasingly, I’m trying to find startups other people aren’t looking at.

I’m using OpenVC to meet founders who haven’t caught on with investors yet. In January, I met Kai, founder of Cryopets.

He’s freezing dogs and cats so we can revive them when veterinary medicine improves. I was able to invest at a much more reasonable valuation than the typical hot AI agent startup in SF.

I’m also going to Japan to meet amazing founders with little access to capital. When I put money where it’s most needed, returns should be higher.

My Strategy for The Rest of 2026

I want to keep my median entry price below $20 million. This means that to get my 4x fund, I need an outcome around $6 billion.

Difficult, but doable.

I expect to do most deals between $10-20 million. Then, I’ll do a handful at higher prices if the founders are exceptional.

I want to keep my entry point reasonable. But I also don’t want to lock myself out of the next great startup.

This is why I focus on median price rather than a hard limit.

Wrap-Up

In the midst of this AI mania, it’s temping to throw money at everything that moves.

I’ve seen all this before in 2021. Everyone was convinced that SaaS was headed to the moon. Why not pay a hundred times revenues?

I refused to do that. Five years later, I’m very happy with that decision.

I always want to back awesome founders. But not at any price.

If that leads me to miss a few deals, so be it.

How I’m Investing at Reasonable Valuations In the Hottest Market Ever

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