Exploring Alternative Investments & Self-Directed IRAs

There’s a tax strategy we keep coming back to in conversations with investors this year, and the current market is what makes it timely.

Crypto is well off its late-2025 highs. Most investors read that as a reason to wait. But for anyone holding a Traditional IRA, a drawdown is precisely when a Roth conversion gets interesting: you convert at today’s depressed valuations, pay tax on the smaller number, and every dollar of the eventual recovery compounds tax-free. The volatility that makes this asset class uncomfortable in a taxable account is exactly what makes it powerful inside a Roth.

The mechanics matter, though — what a self-directed IRA can actually hold, how money moves between custodians without triggering tax, when a conversion makes sense and when it doesn’t, and where alternatives fit in a portfolio built for real financial goals rather than headlines.

In this webinar, we cover all of it. I joined a panel alongside three people who each own a piece of this puzzle:

• Tia Henderson (Forge Trust) — the self-directed IRA custodian’s view: what’s permissible and how it works

• Robert Mowry (Del Mar Life Sciences) — the tax strategist’s view: moving retirement money tax-free, and the Roth conversion decision

• Andy Chong, CFA, CEPA (Highline Wealth Partners) — the wealth manager’s view: where alternatives belong in portfolio construction

• And I’ll cover the digital asset case — why this asset class, and why this entry point

Thursday, July 30 · 11:30 AM PT / 2:30 PM ET