Founder & CEO at Play Money

I sat on the sidelines for six months before I wrote my first check. I was sure I didn't have the knowledge or the money to be an angel investor.
I was wrong on both.
Uber. Poppi. Airbnb. The investors who made the most money got in before the acquisitions and IPOs. You don't need a secret handshake, a giant windfall, or a finance degree to do the same.
When you write that first check, you decide what problems get solved and who gets to solve them. Your fingerprints are on the future.
In six weeks, you'll trust the investing instincts you already have, get the frameworks to back them up, and be excited to write your next check — whether it's your first or your fifteenth.
Go from curious → capable → confident. You'll leave with your first angel check written and a plan for the next.
Every career move you've made, every person you've hired, every product you've loved early. These are the instincts great angels use.
SPVs, SAFEs, K-1s, markups, exits -- we walk through every term in plain English, so the language never gets in the way of the decision.
Learn how successful angels and VCs evaluate deals. Then build your own framework for what makes you say "I'm in!" or "I'll pass."
The math to set your check size and build a portfolio that works like an asset class, not a handful of lottery tickets.
How to turn your 401(k), IRA, or donor-advised fund into angel capital hiding in plain sight.
From the moment you click invest through tax time and exits, we walk through every step so nothing catches you off guard.
What separates a good angel from a great one isn't the check. It's the intro, the advice, and knowing when to lean in. We show you how.

3x Founder. Active angel for 50+ companies. Ex VP at Yahoo, Mentor at Techstars.
You've been angel-curious (maybe even taken a class), but still figured it was for people in tech or finance, so you haven't taken the leap.
You've backed products you loved before they got big. You just didn't get paid for your taste, and you're ready to start.
You've got money sitting in a 401(k), IRA, or DAF that you know could be doing more, but no one has shown you how to activate it for angel.
Lifetime access
Go back to course content and recordings whenever you need to.
Community of peers
Stay accountable and share insights with like-minded professionals.
Certificate of completion
Share your new skills with your employer or on LinkedIn.
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6 live sessions • 34 lessons • 6 projects
Oct
5
Oct
12
You inspired me to take the plunge and make my first investment! Seeing this company, in particular, helped me to clarify for myself the kind of change I want to be a part of.

Holly Schneider Brown
This has been the clearest and most approachable venture education I have ever experienced. I say that after being a part of a bootcamp that gave many of these terms without the background. Please continue to empower us.

Jacalyn Chapman
You showed a visual of your portfolio. It was about 30 companies over three years, a mix of $1,500 and $2,500 checks. And the image of it, I was like, yes, I'm doing that. It has really made decision-making so much easier for me.

Diana Ecker
Cheryl taught one of our new investor WAVE seminars. Amazing! She was down-to-earth, spoke in a language our angels could understand. Passionate. Educated. And just darn cool.

Jennifer Jeronimo
I’ve been angel investing for over 20 years and, without fail, always learn something from time with Cheryl!

Pam Scott
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