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The Angel Investor Playbook
How smart angels find better deals, think sharper, and keep more of what they earn

I’ve been speaking a lot more with people in the startup ecosystem. As an angel investor, I wanted to share some of the best insights and resources I’ve found to help people make more money, faster.
This week at a glance:
💡 Deal Flow: How I find great start up deals (and you can to!)
📚 Analyzing Deals: Zero to One – A great resource for any angel, new or old
📉 Financial Wizardry: Keep more of your own money
Where the Good Deals Come From
Hint: not your DMs

This image is AI-generated. Any names or messages shown are entirely fictional and not based on real individuals or communications.
I get startup pitches in my LinkedIn inbox all the time.
I still take the calls — not because I think the idea is great, but because I like meeting founders. It’s a good way to stay connected to the game.
But here’s the truth:
I’ve never found a great deal from a cold DM.
The best startups I’ve seen?
They came through a friend.
Or a founder I already trusted.
Or another investor who’d done some vetting.
Why?
Warm intros come with built-in signal.
If someone I respect shares a deal, I already know it cleared their bar. That’s a huge shortcut.
So if you’re just starting out: Focus on building relationships before trying to pick winners.
The higher quality your network, the better the deals you’ll see.
Speaking of networks…
Know a startup that needs funding? Thinking about angel investing?
I’m always looking to connect with smart people building or backing big ideas.
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Zero to One
How Peter Thiel reverse-engineers billion-dollar startups
Before he co-founded PayPal, funded Facebook, or launched Palantir, Peter Thiel was a contrarian thinker with a clear thesis:
“Competition is for losers.”
In Zero to One, Thiel argues that the best startups don’t enter crowded markets — they create new ones. They go from 0 to 1.
As an angel investor, this book changes how you evaluate deals.
Instead of asking, “Is this a big market?” You start asking:
Can this founder own a niche?
Is this 10x better — or just 10% different?
What secret are they building on?
In Chapter 13, Thiel even gives you a 7-question framework to vet billion-dollar potential.
If you're thinking about writing your first check — or your tenth — this is the book to read.
👉 Grab Zero to One here (affiliate link — supports the newsletter!)
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Angel Tax Credits
A Hidden Edge for Startup Investors

Who doesn’t like more money?
Boost returns, de-risk deals, and support the startup ecosystem…
Sounds too good to be true, right?
If you’ve never heard of Angel Tax Credits, you’re not alone — but they might be the most underrated tool in early-stage investing.
Here’s how they work:
Many states offer tax credits to investors who back startups based in that state. These credits can be used to reduce your state tax bill — or even sold to other taxpayers for cash.
It’s a win-win-win:
Investors get a boost to their returns and downside protection
Startups become more attractive to capital
States drive job creation and innovation
The catch? Every state program is different — and most people don’t know how to access them.
That’s where ATC (Angel Tax Credit Co.) comes in.
They’re the leading facilitator of angel tax credit transfers in the U.S., and they’ve built a simple marketplace where:
✅ Investors can buy credits to reduce taxes
✅ Founders can offer credits to attract capital
✅ Sellers can monetize an otherwise illiquid asset
If you’re an investor looking to improve your after-tax returns…
Or a founder raising money in a qualifying state…
Believe it or not, I’m not an affiliate for Angel Tax Credit Co. I just think they’re solving a real pain point for investors and founders.
(But hey ATC, if you’re reading this — call me 😉)