I just missed out on $157,000. Last year, I passed on a startup that is now raising at 25x the valuation. Here’s how I blew this deal, and what I’ll be doing differently next time…

Why I Passed 

We’ll call this startup Supercorp. In April 2025, I had an opportunity to invest in their seed round.

They had solid growth of 3.5x year over year. The founder had a good technical background, and tthey were nearing $2 million ARR.

What worried me was the market. Their segment had fewer than 2,000 potential customers, according to my research. 

Even at Supercorp’s healthy ACV, that produced a TAM of just $500 million. What’s more, their growth was a little below what I was seeing in some other startups.

What I Missed

The biggest thing I missed here: focusing too much on their initial customer segment.

They soon expanded way beyond it. Now they’re building for many industries, shipping new products, and massively expanding their TAM.

I also didn’t pay enough attention to the founder’s background. His decades of experience in the market he’s serving gave him a huge advantage. 

Unconscious Bias?

There may be another reason I missed Supercorp. The team doesn’t look like your typical startup.

They’re not 22. They don’t live in San Francisco or New York.

Did that bias me unconsciously? Hard to say. 

But it’s possible. When I meet less traditional teams in the future, I’ll have to look at them extra closely.

What This Miss Cost Me

The seed stage deal was done around $20 million. Now, they’re raising at $500 million. 

This was a syndicate deal, and it had some significant fees on it. But after fees and dilution, my typical $10,000 check would still be worth $157,000. That’s a 16x return in 14 months.

Instead, I made nothing. Yeah, it sucks.

Wrap-Up

In the end, I got hung up on TAM math. What I didn’t see was a strong team with a great product who’d find someone to buy it. 

Every investor misses deals. This one stings, but there’s always another. 

Hopefully I’ll nail the next winner.

I’m off to the woods for a camping trip. ⛺ Have a great weekend, everybody!

More on tech: 

38 Words Got This Founder on My Calendar — Here’s the Cold Email Formula That Wins

Fundraising Friction is Killing Your Round – Here’s How to Remove It

Meet My Latest Investment: Perfectly

Save Money on Stuff I Use:

Fundrise

This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

More on Fundrise in this post.

If you decide to invest in Fundrise, you can use this link to get $100 in free bonus shares!

Wispr Flow

I used this app every single day to dictate to my computer, I’m even dictating this text using Wispr Flow! It’s way better than Apple’s native dictation.

My productivity is up about 25% since I started dictating rather than typing. I’m also less tired and stressed.

Get a free month of Wispr Flow Pro here!