What does an angel return calculator leave out?

A calculator cannot account for fees, the chance a company fails, or when an exit actually happens. It also cannot show how deal terms, such as liquidation preferences, change who gets paid first. Use it to understand the mechanics and to compare check sizes, not to predict a specific outcome. The model is only as good as the assumptions you enter.

BlogInvesting

Model Your Angel Returns Before You Write the Check

By Cheryl KellondFounder & CEO

October 19, 2026

Originally sent to Play Money subscribers · May 2025

Part of our ongoing Tuesday series on how angel investing returns are modeled, from check size and dilution to what one check can realistically deliver.

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🤓 Q: How should I think about returns on each of my Angel checks?

I get nervous about sharing "Angel Investment Calculators" because they don't capture the full nuance that comes with early-stage investing.

BUT, a simple investment calculator is the best way to get a feel for:

What different check sizes mean
How time and dilution factor into investing
How to wrap your head around the fees that come with SPV investing

Here is a calculator to help you model individual Angel investment returns that a friend put together (with some of our own spin layered in).

Play with the Calculator

One of the biggest observations I had with the calculator is that, although it's fun to see the impact of a billion dollar exit, if I am allocating a single-digit percentage of my financial portfolio to angel investing (smart) and building a diverse portfolio (smart), the upside from a single angel check is most likely not life-changing (until it is).

And that is ok.

What is truly life-changing is the impact that even small checks, when added together, can have throughout the economy, in our local communities or for historically under-resourced problems and founders, and on our own emotional fulfillment and enrichment.

If you are not the calculator type:

What has also been life-changing are the investments I almost made but didn't. My one that got away story lives rent-free in my mind every day. 🤦🏽‍♀️

And if you want a real-life spin on the calculator, here is a great write-up on how different classes of investors fared when Loom exited in late 2023.

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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Frequently asked questions

Start with your check size, the valuation when you invest, and how many years it may take to reach an exit. A calculator shows how a single check changes across different exit values. The results are rough, though. A billion-dollar exit makes a dramatic chart, but for an investor with a diversified portfolio, one check is unlikely to be life-changing on its own. Most of the value comes from many small checks added together over time.

Dilution lowers your ownership each time a company raises a priced round. Your share count stays the same, but the total number of shares grows, so your percentage shrinks. A calculator that includes dilution shows how much of your stake may remain at exit. Dilution does not always reduce your payout, though. A company that grows in value can still leave you with a larger return, even with a smaller percentage.