I am stuck in a deal. What do I do next?

That is the question driving this episode. And Brian Sutton is uniquely qualified to answer it because he is living it right now as a limited partner in a lot of deals that have gone sideways.

In Episode 12 of Lessons the Hard Way, Brian and Sam sit down for one of the most honest and unexpected conversations the show has had. What started as a tactical breakdown of what to do when you are stuck in a bad real estate deal turned into something more important: a conversation about managing your state, stopping the self-blame, and figuring out how to get your mind unstuck before you can get your money unstuck.

Two Waters Capital is on the other side as an operator. Brian personally is not. And he is not hiding it.

In this episode:

• The stages of grief for a bad real estate deal and how Brian went through all of them

• Why the decisions you made were not bad decisions — the economy hit everyone

• Stop beating yourself up: most of the operators you trusted are great people who got crushed

• Why swearing off real estate and going to Bitcoin or mutual funds is the wrong answer

• Sitting on your hands is not a strategy — every action and inaction has a consequence

• The coin analogy: you have been squashed long enough, it is time to flip to the other side

• How the most successful operators change their state fast and focus on opportunity

• Staying in the eye of the hurricane: the question Brian and his wife ask each other during chaos

• The people piling in last always get hurt worst — and why now is when to pay attention

• Two Waters took a four year hiatus for a reason: they saw the overheating coming

• What happens when you change your state and focus on what is in front of you instead

Subscribe for weekly episodes. New deal autopsies and hard lessons every week.

Two Waters Capital: 2waterscapital.com

#lessonsthehardway #twowaterscapital #realestateinvesting #multifamilyinvesting #realestatelessons #stuckinareal #investormindset #accreditedinvestor #commercialrealestate #realestatepodcast

0:00 Cold open: I am stuck in a deal, what do I do next

0:54 Show intro and welcome back

1:39 Brian's confession: stuck in a lot of deals as a limited partner

2:28 Going through the stages of grief on a bad deal

3:49 Those were not bad decisions — stop beating yourself up

4:43 Why swearing off real estate is the wrong answer

7:01 Sitting on your hands is not a strategy

8:05 The most successful operators change their state fast

9:33 You have been squashed by the coin — time to flip it

11:41 Change your state first, then focus on opportunity

12:58 We only have today: the only real solution is to move forward

14:48 New strategies coming out of the downturn

15:29 Getting investors on the other side of the coin

16:24 People who pile in last get hurt worst — why now is different

17:28 Two Waters took a four year hiatus and why

18:24 Staying in the eye of the hurricane

19:24 Focus on the massive opportunity ahead

20:33 The magic carpet ride: it is never going to be flat

21:19 What can we personally do to get our minds unstuck

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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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Scott Williams finished his partner buyout at 11:59 PM on December 31st, 2025. He headed into 2026 with the biggest pipeline Aline Capital had ever built. Then the Iran conflict broke out and took the 52-week low in interest rates with it.

In this episode of Lessons the Hard Way, Sam sits down with Scott Williams, founder and managing partner of Aline Capital, a commercial real estate advisory firm focused on investment sales and capital markets transactions across the Southeast. Scott has spent the last two years navigating a partner split, a compressed buyout, a frozen transaction market, and a macro environment that kept refusing to cooperate. He is still standing. And he has a lot to say about how.

In this episode:

• The partner split in Q4 2023 and what it meant to go through a tough market without that support

• Completing a five year buyout in two years, entirely out of cash, while transactions fell 40%

• Why survive till 25 never delivered and what 2026 actually looks like on the ground

• We hit the 52 week low on Friday, February 27th. Iran broke out on Saturday the 28th.

• The Gap and the Gain: why driven people should always measure backwards, not forward

• The racehorse principle: treating yourself like a million dollar investment

• Strategic Coach, Dan Sullivan, and planning to live to 137 as a business framework

• The bridge loan debacle, the distressed fund opportunity, and why Brian Sutton had the right idea early

• Tariffs, inflation, a possible rate hike in the futures market, and what Scott actually expects from here

• Why uncertainty is the norm and the only way to underwrite deals right now is a range of outcomes with probability weighting

• Human intuition vs. AI and what separates the best operators in a noise-heavy market

Subscribe for weekly episodes. New deal autopsies and hard lessons every week.

Connect with Scott Williams and Aline Capital: alinecapital.com

Two Waters Capital: 2waterscapital.com

#lessonsthehardway #twowaterscapital #realestatepodcast #realestateinvesting #multifamilyinvesting #capitalmarkets #commercialrealestate #accreditedinvestor #realestatelessons #scottywilliams

0:00 Cold open: the most challenging professional quarter of my life

1:05 Welcome: introducing Scott Williams of Aline Capital

2:09 Setting the stage: 2015 to 2022, easy growth and the Covid faucet

4:19 When things got hard: 2023, rate hikes, and the partner split

5:57 Compressing a five year buyout into two years during a down market

7:15 Survive till 25 never came: the rate cut that kept getting pushed

8:23 Finally feeling relief, then Iran broke out on February 28th

10:07 Managing through it: what Scott is doing differently right now

12:05 Gratitude practice: pulling yourself out of the negativity deliberately

13:49 Writing it down: three ways the day could go better than expected

15:49 The Gap and the Gain: always measure backwards not forward

17:49 Swimming ten miles and looking back at how far you have come

18:35 The physical game: workouts as a non-negotiable in hard seasons

20:11 The racehorse principle: treat yourself like a million dollar investment

21:24 Planning to live to 137: the time extender framework from Dan Sullivan

22:32 Embrace the suck: two years is a blip when you zoom out far enough

24:11 Back to the market: the bridge loan debacle and where distress is headed

25:38 Brian Sutton, Two Waters, and the distressed fund thesis

28:11 Where did all the distress go? The extend and pretend explanation

30:00 Tariffs, Iran, and the inflation shock hitting 2026

36:39 The bond market as the smartest money in the room

37:25 CPI, rate cuts baked out, and a rate hike appearing in the futures market

38:35 Scott's outlook: what needs to happen for 20 to 30 basis points to come out of the curve

40:37 Don't predicate a deal on things getting easier: underwrite what is in front of you

42:17 Human intuition vs. AI in an uncertain market

43:30 How to reach Scott Williams and Aline Capital

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