The Diligence Trap Every Angel Falls Into
Originally sent to Play Money subscribers · April 2026
Part of our ongoing Tuesday series on angel investor psychology — conviction, decision-making, and the mental traps that keep good angels from writing great checks.
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💎 My own fundraising has been sucking at my soul a bit. So I took a little work-joy bender. On Friday, I filled my day with customer conversations. Monday I carved out two hours for deep dive diligence with two founders doing wildly hard things.
And I noticed something I had never noticed before.
-- C2K
I love businesses with a bit of complexity. So Monday's pitch day was heaven to me.
One founder is running a circular economy company - essentially three huge standalone businesses tied together. The other is installing urban infrastructure.
Both businesses have rare founders who can make them work.
One could tell you 4 levels of unit economics for the 6 different approaches to the problem she was solving in all 5 cities where her product operates. The other could explain her miles-per-service metric, her route-density economics, and a regulatory sequencing trick that reduces her permitting overhead, in a way that had us all nodding our heads in agreement.
With every answer, the room leaned in deeper.
...and maybe less likely to write a check.
There are a million reasons to say no to investing in any startup. A million!
But the operational strengths needed for success in both businesses weren't moving us closer to a yes.
The details devoured the emotional magic.
My analytical brain turned on, and my imagination turned off. I started the day ready to write checks to both. I left, dragging my feet.
This is a trap (often a gender biased one).
And I don't play the gender card lightly.
If I were a "real VC," I'd spout some blather about "first principles." But thankfully, I am not, so I rolled my own version of my favorite diligence question for startups solving problems I care about.
Elizabeth Yin is the social media sage and General Partner at Hustle Fund. She loves to ask: "What happens if everything goes right?"
My version of that question this week has become: Is this inevitable?
✅ Urban EV charging where people actually park. Inevitable.
✅ Bio Waste recycled into things that replace petrochemicals. Inevitable.
✅ And for Play Money: new private market investors hungry to reshape the future. Inevitable.
Someone will win in these spaces one day. And the raw rub is that the ones most likely to succeed aren't always the ones who can harness the emotional wave needed for early-stage investment.
Balancing the two is really, really hard. I know. I am a founder.
As an investor, I need to avoid falling into the trap.
One person on the call commented:
"If I don't invest and this becomes a huge hit, I'll kick myself because it was obvious. But if I do invest and it's a total failure, I'll kick myself because it was obvious." 🤦🏽♀️
A killer founder brave enough to tackle a complex problem that needs to be solved is never a bad bet. The founders who can both see the big vision and operate in the weeds are the ones who'll still be building when the world catches up.
Write the darn check.
-- C2K
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