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How to Invest Your Retirement Account in Real Estate
Episode 1110th June 2026 • Lessons The Hard Way • Brian Sutton
00:00:00 00:35:23

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You can use your retirement account to invest in real estate. Most people have no idea.

In this episode of Lessons the Hard Way, Sam sits down with Kelsey Dineen, 16-year veteran and senior member of the self-directed IRA and 1031 exchange team at Equity Trust, founded in 1974. Kelsey breaks down exactly how accredited investors are using retirement accounts to invest in real estate syndications, funds, and alternative assets in a tax-sheltered environment and why it is simpler than most people think.

Two Waters Capital investors have used Equity Trust to invest in Two Waters syndications and funds. This is the inside conversation on how that actually works.

In this episode:

• What a self-directed IRA actually is and what it is not

• The top three reasons sophisticated investors move down this road

• Diversification beyond publicly traded assets into off-market opportunities

• How to use retirement funds in a tax-sheltered environment to amplify wealth

• The step-by-step setup process at Equity Trust and how long it actually takes

• Penalties, taxes, and what investors need to know before making the move

• How depreciation is affected when investing through a retirement account

• What account types can be rolled in: 401K, Roth IRA, SEP IRA, and more

• Can you use just a portion of your retirement account? Yes — here is how

• Real success stories from investors who were reluctant and then moved forward

• How to get in touch with Kelsey and get started with Equity Trust

Ready to open an IRA? Online application link is https://apply.midlandtrust.com/Welcome

Referral/Group Code to open your IRA for free ($50 setup fee waived) is "coverfullamount"

Link for a FREE consultation call with Kelsey Dineen, CISP: https://calendly.com/k-dineen-trustetc/30min

Two Waters Capital: 2waterscapital.com

#lessonsthehardway #twowaterscapital #selfdirectedira #equitytrust #realestateinvesting #multifamilyinvesting #retirementinvesting #accreditedinvestor #realestatepodcast #taxsheltered

0:00 Cold open: we don't vet, we don't do due diligence

1:09 Welcome: introducing Kelsey Dineen of Equity Trust

1:58 Kelsey's story and how she helps investors

6:14 What kind of investors end up working with Equity Trust

8:52 What a self-directed IRA is and what it is not

10:33 The top three reasons investors move down this road

12:22 Diversification: getting off publicly traded markets

15:22 The three reasons revisited: diversification, tax sheltering, and structure

18:01 Penalties and taxes: what investors need to know

21:05 How depreciation works inside a retirement account

23:27 What account types can be rolled in

26:08 Can you use just a portion of your retirement account

28:27 The setup process: step by step with Equity Trust

30:41 Success stories from reluctant investors who moved forward

32:52 What question did we not ask

33:49 What Kelsey is excited about moving forward

34:06 How to reach Kelsey and get started

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