Emotional Armor When the Zeros Hit
Originally sent to Play Money subscribers · May 2026
Part of our ongoing Tuesday series on building your angel investing thesis — frameworks, personal conviction, proxied diligence, and why writing checks teaches you more than any checklist.
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💎 The best part of being a founder is that every customer conversation is a treasure chest. We brought Angel 101 back for the summer (on the first Wednesday of every month). May’s was magnificent.
The question that kicked us off: “Do you need a thesis?”
The newsletter basically wrote itself.
-- C2K
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Invest in what you know.
Have a thesis.
Do your own diligence.
Wah Wah-Wah Wah Wah.
If you are a VC, all of this advice makes sense. I mean, you are investing and trying to attract OPM (other people’s money). You have to let them know your rules for making money.
But angels? We are not small VCs.
It’s our money, our rules.
And sometimes the best way to figure out your own rules is the flip of what you think: Write the checks, figure out the rules as you go.
Here are my four favorite stories from this month’s session:
🏤 One person started with pages of diligence questions. 30 checks later, she’s boiled most of it down to a single request: “Send me your last three stakeholder updates.”
If they hem and haw, she’s out.
By writing a few checks, she found her shortcut to assess execution, clarity of thought, and communication. A whole investing thesis in one sentence. 😈
♻️ Another focused on “health and happiness of women, mothers, families.” Broad enough to cross CPG, childcare, and tech but also targeted enough to filter out the noise. As she talked, it was clear that she had dug deep into the science behind clean ingredients and materials and had a sophisticated POV on the next-gen consumer.
I left convinced that her personal passions had given her a better frame for the future of CPG than 3 of the last 4 VCs raising funds in this space I’ve talked to.
🤖 A third had a robo-advisor buying her defense-tech and private-prison stocks when she wasn’t looking. After her new wealth manager untangled this “Naughty List”, she sold her positions and donated the proceeds to her DAF.
Her “Palantir Payout” is now funding female founders on Play Money. 🔥
Your thesis is what your money says about you when you’re not in the room.
She found what her money had been saying about her...and ran the other direction.
For me, I’m a baby check writer. But I have an endometriosis biotech company in my portfolio with a check 5x my typical size.
I pulled from my investment and charity budgets. My money, my rules, right?
I can’t diligence a biotech myself, but that shouldn’t keep me out. We trust proxies all the time. Yelp reviews, IG influencers, our best friends. On this one, I proxied my diligence to Portfolia and a biotech deal lead I went to grad school with, and then jumped in!
But what if that conviction-based proxied-diligence bet goes south?
One of the experienced investors on the call summed it up best:
My thesis isn’t just a filter. It’s emotional armor when the zeros hit.
Chances are you’ll back that founder again. 😉
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