The Capital Shift

If your W-2 is doing well, the tax bill that comes with it probably doesn’t feel like a reward. In this episode of The Capital Shift, Roger sits down with Greg Herlean — founder of Horizon Trust Company, a self-directed IRA custodian with 9,000+ clients and over $2 billion in assets under administration — to break open a strategy that’s been legal since the 1970s but that almost nobody’s advisor mentions: using your retirement funds to invest in what you actually understand. Greg explains how a self-directed IRA lets you move retirement money into real estate, lending, fix-and-flips, and private deals — growing it tax-deferred, or completely tax-free inside a Roth. He and Roger also dig into the quieter opportunity hiding in plain sight: the 18+ million dormant retirement accounts left behind at old employers, and why there’s a real chance you (or your spouse) are sitting on one without knowing it. Inside the conversation: the two biggest reasons people never do this (and who genuinely shouldn’t), why 80% of Greg’s clients invest passively as lenders and fund partners rather than operators, Horizon’s cost structure, the “disqualified persons” rules that keep you out of trouble with the IRS, traditional vs. Roth in plain English, and how pooling IRAs with a partner can unlock deals you couldn’t do alone. This one pairs directly with the RealWise Collective: take the Capital Readiness Index, find your number, and find the Stewarts whose numbers complement yours. This episode is educational and not tax, legal, or investment advice. Rules and outcomes depend on your individual situation — talk to your CPA or advisor before acting. Roger is a client of Horizon Trust.

You think you know what loan product you need. A professional lender, informed by current market conditions, your specific situation, and real deal experience, might suggest something different. The difference between listening to that informed guidance before you're locked in versus after could be six figures and a blown closing. The Before You're Committed series is about the professional team that informs every decision a successful real estate investor makes. Taylor Sherman isn't just a lender—he's a real estate investor himself, closing deals weekly while navigating the gap between what forums say works and what actually does. In this conversation, we explore current market conditions, why your strategy needs to adapt without changing your goals, and why talking to someone who informs rather than dictates is the fastest way to protect your capital and keep deals on track. Your team is your entire advantage. Let's start with the lender.

You've heard which asset classes reduce taxes. You've read the marketing. You've seen which syndication sponsors emphasize depreciation and cost segregation. But what if the real story—the one that emerges from actually examining the data—is different from what everyone's selling? Jeff Hiatt isn't an operator. He's a diagnostician. Since 1996, his firm has completed 28,000 cost segregation studies across every major real estate asset class. That means he's examined multifamily, self-storage, commercial, industrial, hospitality, short-term rentals, triple net leases—thousands of deals, the actual numbers, the real tax implications. In this episode, Jeff brings The Capital Shift Compass into his office and diagnoses each asset class through the lens of tax efficiency—his specialty. But here's the tension: tax efficiency doesn't exist in a vacuum. It comes with tradeoffs. Some asset classes that promise the biggest depreciation benefits require operational complexity. Others deliver reliable tax shelter but sacrifice equity leverage. And some, frankly, are traps disguised as opportunities. This isn't about which asset class wins. It's about understanding what the data actually shows when you strip away the marketing and examine the mechanics. If you've been making deployment decisions based on social media advice or FOMO, this conversation is a course correction. Sometimes the best investment decision isn't choosing the highest-tax-benefit asset. It's understanding what that tax benefit actually costs you in other dimensions.

Everybody was chasing the same $100/door multifamily deal. Tim Woodbridge made a hard left turn - from bedside nurse to mobile home park operator with 30 communities, 1,400 pads, and $55M AUM. This week, that contrarian bet spins the Compass. Tim didn't run a hundred spreadsheets. He heard Frank Rolfe on a podcast, found a park an hour outside Charleston, and took it down to "figure it out." His line: "I'm not smarter than anyone - I'm just braver." We run mobile home parks through all four points of the Capital Shift Compass - one of the rare asset classes that carries real weight in every direction: Cashflow Creation: Monthly distributions starting month 3. Never missed one. Capital Velocity: 5 to 7 year hold, with a refi window underwritten conservatively. Equity Leverage: Target minimum 2x equity multiple; typically 16 to 20% IRR. Tax Efficiency: Cost segregation on every deal - roughly a $150K negative K-1 on a $100K investment in year one. (An honest word on depreciation recapture too - talk to your CPA; not investment advice.) But Tim charts highest on purpose: affordable housing done like a professional, not a slumlord - gradual rent, real improvements, dignified living - and a mission to end homelessness in the U.S. by 2050. Stick around for the Voyagers bonus: 5+ years clean and sober, the mindset that rebuilt his life, and what the Boardroom mastermind has meant to his business. In this episode: (00:00) Record stores, Fender bass, and 80s industrial - two music nerds warm up (05:00) From nurse to real estate: chasing growth, not comfort (11:00) The inflection point - if someone else did it, I can too (15:00) Why mobile home parks (Frank Rolfe plants the seed) (17:00) Take action first: buying the first park near Charleston (21:00) The portfolio today - 30 parks, 1,400 pads, $55M AUM (22:00) The thesis: lot rent, NOI, and raising rent the right way (28:40) Spinning the Compass: cashflow, velocity, equity multiple (34:00) The clincher - cost seg, the $150K K-1, and depreciation recapture (42:00) Who the ideal WCG investor really is (50:25) Bonus (Voyagers): sobriety, the five D's, and the Boardroom (1:02:24) The big audacious vision - ending homelessness by 2050 Connect with Tim & WCG Investments: book a call or join the deal list at wcginvestments.com The Capital Shift Podcast helps you develop the identity, standards, and decision-making to responsibly move capital from abstract markets into real, governed assets. Every operator gets run through the Compass - Tax Efficiency, Equity Leverage, Capital Velocity, and Cashflow Creation. Companion scoring episode with Jeff Hyatt drops the following week.

SteelPoint Capital was built on a simple premise: real estate investors need fast, reliable financing. Traditional lenders take weeks or months and come with red tape. Hard money lenders understand the asset and the operator. Here's what that means in practice: 10-12% fixed returns paid monthly (or compounded), 24-48 hour underwriting, first lien position on every deal, and a lender who's actually a real estate investor themselves. After six years and zero defaults, SteelPoint's model works because TJ and his partners won't lend on a deal they wouldn't take over if the borrower defaulted. But there's a deeper story here about why discipline, transparency, and a belief in something bigger than yourself actually compounds into better business. This episode covers both the mechanics of deploying capital into hard money funds and the character required to do it with integrity.