Angel Investing Through a Roth IRA (The Tax-Free Sniper Rifle)

How to turn long-term retirement dollars into asymmetric startup returns.

November 21, 2025

If Part 1 was the wake-up call, Part 2 is the first major unlock.

Because today we break down how angel investors legally invest in startups through a Roth IRA.

Roth IRAs are misunderstood.
People think they’re for index funds and retirement calculators.

But that’s not the full story.

Inside the tax code, the Roth IRA is the ultimate vehicle for asymmetric bets.

You put in after-tax dollars.
You take out every penny of growth:

That’s why Peter Thiel’s $5B Roth IRA was possible.
And why it’s still legal today.

Let’s walk through exactly how it works.

A Roth IRA is simple:

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