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How to Use Your 401(k) or IRA to Invest in Opportunities That Aren't Traditional Stock

By Harry Shurek · Originally published June 29, 2020 · Updated July 30, 2026 · 3 min read

The self-directed option

Most retirement accounts sit in funds because that is all the custodian offers — not because the law requires it. A self-directed IRA (and in some cases a solo 401(k)) can hold real estate, private company interests, notes, and other alternative assets, opening retirement capital to opportunities the brokerage menu never shows.

The rules that actually bite

Prohibited-transaction rules are the minefield: no self-dealing, no transactions with disqualified persons (you, close family, entities you control), no personal use of account assets. Violations can disqualify the entire account and trigger tax on all of it. Certain income inside the account can also generate UBIT. None of this is fatal — all of it demands professional guidance before the first dollar moves.

The cannabis wrinkle

Cannabis-adjacent investment through retirement accounts adds federal-illegality questions on top of the usual rules, and custodians differ sharply on what they will hold. Real estate leased to operators and ancillary businesses are the common lanes. This is precisely the kind of decision to model with someone who knows both the retirement rules and this industry — talk to us before acting, not after.

Talk to a cannabis accountant, not a generalist

MCA has served licensed operators exclusively since 2015 — 100+ businesses across 30+ states. Free consultation; bring your last return and current P&L.

Related: Individual Tax Planning · Investment Due Diligence

This article is general information, not tax advice.