How AI Is Changing Angel Investing (And Why It Matters)
Originally sent to Play Money subscribers · September 2025
Part of our ongoing work to make angel investing more structured, human, and scalable.
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💎 I’m supposed to be yapping about investing and product features.
But I need a minute.
Most of you haven’t met Tina. She’s our Head of Founder Success & Deal Flow. She joined Play Money a couple of weeks after launch and has put her heart and soul into this business as a true founding partner.
This week I met her real heart and soul — her new husband (who I see on Zoom every day) and their tight-knit families I’ve heard so much about.
In a world that feels increasingly un-human, there is something powerful about investing in hope.
Backing a founder.
Building infrastructure.
Or even slowing down long enough to celebrate what matters.
Pinch me.
Now let’s talk about the other kind of team member.
Why Angel Investing Feels Overwhelming
If you’ve ever made an angel investment, you know this part.
Deal memo.
Pitch deck.
Founder video.
Q&A thread.
Investor POV.
Term sheet.
SPV docs.
Every deal structure is different:
- Convertible notes
- Priced rounds
- Revenue or dividend hybrids
- SAFEs
- Cap tables that make your eyes cross
Angel investing isn’t hard because founders aren’t interesting.
It’s hard because information is fragmented.
You’re stitching together context manually every time.
And most angels are doing this at 10pm after their day job.
AI for Angel Investors: Meet Casey AI
Over the past six months, Casey quietly became the backbone of our back office.
SPV updates.
Founder questions.
Closing logistics.
Wire confirmations.
Casey made everything easier.
Now we’ve taken that same “make everything easier” magic and turned it outward.
Meet Casey AI.
A built-in assistant designed to help you understand a deal faster and more clearly.
You can ask anything about a deal memo — from the pitch deck to founder videos (transcripts included), Q&As, and investor commentary.
Instead of piecing everything together yourself, Casey synthesizes it.
It’s like having a smart co-investor who:
- Read every line
- Watched every clip
- Modeled every term
- Remembered every detail
So you don’t have to.
Available now on all open deals.
How AI Improves Angel Deal Evaluation
This isn’t about adding chat bubbles to a website.
It’s about lowering the cognitive barrier to thoughtful capital allocation.
Angel investing shouldn’t require:
- Perfect memory
- Financial modeling fluency
- Or 45 spare minutes per memo
If we want more people to participate in private markets thoughtfully, we need tools that reduce friction without reducing rigor.
That’s what we’re building.
How Are You Using AI in Angel Investing?
How are you using AI in your angel investing?
Are you:
- Stress-testing valuation assumptions?
- Comparing deal structures?
- Summarizing diligence threads?
- Modeling scenarios?
Tell us.
We’ll share the best prompts and insights from the community — and it will shape where we take Casey next.
Without stepping into hallucinations or investment advice, of course 😉
— C2K
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Play Money makes angel investing accessible by helping everyday angels build diversified startup portfolios without turning it into a full-time job.
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