Angel Investing in an AI World: Why Your Own Conviction Matters More Than Ever
Originally sent to Play Money subscribers · April 2026
Part of our ongoing Tuesday series on building your own angel investing thesis — conviction, frameworks, and how to think independently in a fast-changing market.
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🤔 Two years ago, I invested in a later-stage SaaS company. Fast-growing. Profitable on a dime. Clear exit path. A fund I really respect was doubling down.
I wanted to add some late-stage exposure to my portfolio to create a closer-term liquidity event. I didn’t think deeply about the company. SaaS infrastructure is outside of my rubric for “things I care about.” I just saw “smart money” moving and called it good enough.
That was a mistake.
AI changes everything and nothing all at once
Fast forward 24 months and AI has changed the math on everything. The company is scrambling to pivot. And I don’t feel great about the bet.
But the problem isn’t the deal. The problem is, I never built my own view on it.
I outsourced my conviction to someone else.
And that signal I used to trust, a respected fund doubling down, doesn’t carry the same weight anymore.
Fund managers are drinking from the same fire hose. Everything is moving so fast.
We’re almost on a level playing field.
And honestly? That’s the exciting part.
Whole new categories are being created right now. Whole new businesses that couldn’t have existed two years ago are happening. Founders solving problems the gatekeepers have been blind to, are finally able to build on their own terms.
I’m watching what AI is doing to my own company and I am giddy. 🚀
But I know angels who were writing checks two years ago who’ve completely stopped. Everything is moving so fast it feels easier to sit it out.
👉🏼 You do not want to be on the sidelines for this.
Don’t give away your gut
The fix? Build your own point of view.
Some parts of that POV shouldn’t change, like:
“Do I care about this problem space?”
“Does this solution, product, or brand excite me?”
Notice how I ignored that with this investment. 🤦🏽♀️
But one has to change. Right now, every POV needs to expand to include AI.
The great part? You don’t need to be an AI expert or be able to predict the future. Just ask:
- WWCD: Could Claude just do what this company does?
- Does the company sit on its own proprietary data (or even better) its own evolving data model that Claude could never know?
That’s it.
The basic understanding of the business gives you the answer. No expertise required. That’s your permission to write your next (or first) check.
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Pro tip: I ran my existing portfolio through those two questions. I felt better about some bets and worse about others. Both were useful.
And that late-stage SaaS company? It was a no-code website builder. 🫣
I ran it through those two questions. And for the first time, I actually have my own view on how I feel about this investment.
No regrets.
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