Invest in Startups Through Your Retirement Accounts

In a recent post on X, I wrote that I wish I had started investing in startups through my retirement accounts sooner.

I spent most of my twenties doing what everyone tells you to do: putting my savings into ordinary Roth IRAs and 401(k)s. I did not learn until my late twenties that those same accounts could own startup equity.

Today, I use an Alto IRA Checkbook LLC, a product Alto unfortunately no longer offers for new accounts, for my angel investments. My Roth IRA owns an LLC, and that LLC writes the checks and holds the startup equity.

I also use Rocket Dollar for a Solo Roth 401(k). Because I am self-employed, I can contribute much more than the ordinary IRA limit and direct those funds into alternative investments.

The distinction matters. I do not have to choose between saving for retirement and investing in startups. The same tax-advantaged pool can finance long-duration, high-upside investments, and the proceeds from successful exits can be reinvested without leaving the account.

I wish I had understood this ten years earlier.