Episode 11

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Published on:

10th Jun 2026

How to Invest Your Retirement Account in Real Estate

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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About the Podcast

Lessons The Hard Way
Real estate investing and life under pressure — the unfiltered truth about what really happens inside the deals.
Welcome to Lessons the Hard Way: Real Estate Investing and Life Under Pressure.
This channel is for serious real estate investors, accredited investors, and operators who want the truth about what actually happens inside real estate deals.
Most real estate content online celebrates the wins - the equity multiples, the exits, and the highlight reels.
But the most valuable lessons in investing usually come from the moments when things didn’t go according to plan.
On this podcast, we sit down with real estate operators, lenders, investors, brokers, and builders to unpack the deals that went sideways, the pressure that followed, and the lessons learned in hindsight.
Hosted by seasoned real estate professionals Brian Sutton and Sam Chillingworth, each episode breaks down:
Real estate deals that went wrong
Market cycles and investment risk
Asset management challenges
Raising capital and investor relations
Tactical lessons learned from failed or difficult investments
How experienced operators navigate pressure and come back stronger
This is not a podcast about flashy lifestyles and overnight success.
It’s a podcast about discipline, resilience, and building long-term wealth through real estate investing.
If you’re an accredited investor, real estate sponsor, syndicator, or serious wealth builder, you’ll gain practical insights from people who have already learned these lessons the hard way.
New episodes every week.
Subscribe to hear real conversations about real estate investing, risk, failure, recovery, and long-term wealth building.

Hosted by Brian Sutton, founder of Two Waters Capital.