CRE Deep Dive

Trevor's LinkedIn

https://www.linkedin.com/in/ktrevorthompson/

Trevor's Email

KTTProperties@gmail.com

Massive Capital

https://massive.capital/

From iFLY VP to CRE Syndications: Trevor Thompson on Due Diligence, Sponsors & Buying in Today’s Market In this CRE Deep Dive episode, Trevor Thompson shares his path from attraction and indoor skydiving operations to commercial real estate investing, including helping open 90 iFLY locations and completing 48 syndications as both a limited and general partner. He explains what syndications are, how he overcame fears of single-family “toilets, tenants, and trash,” and lessons from his first passive deal, including the importance of property-level due diligence and COVID-era rent challenges. Trevor outlines how LPs can evaluate sponsors, spot unrealistic underwriting and return promises, and why education, transparency, and accessibility matter. He discusses recent acquisitions, including a Texas multifamily deal and a 32-bed assisted living project, plus how underwriting has shifted toward stable, fixed-rate debt and stronger risk controls. He emphasizes compounding, avoiding “get rich quick” expectations, and taking action to overcome analysis paralysis.

00:00 Meet Trevor Thompson

01:32 Real Estate Leap

02:15 Syndications Explained

03:19 Creative Deal Lessons

04:32 First Investment Mistakes

06:34 Choosing Great Sponsors

08:39 Property Tours Value Add

11:31 Deal Deck Red Flags

13:35 When To Walk Away

15:10 Buying In Todays Market

16:18 Assisted Living Expansion

17:05 Passion-Driven Operators

17:40 Underwriting in High Rates

19:04 Walking Away From Risk

20:06 Honesty Builds Trust

21:31 Setting Return Expectations

23:33 Investor Community in Action

25:11 Real Estate Is Rich Slow

27:07 Impacting 100000 Lives

29:39 Beating Analysis Paralysis

30:58 First Steps With 50000

32:01 How to Reach Trevor

https://directedira.com/ IRA LLCs for Real Estate: Privacy, Prohibited Transactions, Depreciation, and UBTI/UDFI Explained

Dennis interviews Lindsay Mersino on using IRA LLCs for real estate investing, clarifying that an LLC—especially a single-member LLC—doesn’t automatically create tax benefits. They cover why investors use IRA LLCs for privacy (investing under the LLC name), speed (checkbook control vs. custodian processing), and saving transaction fees for active investors. Lindsay explains fix-and-flip activity limits as a passive-versus-active issue, with a conservative safe zone of two to three flips per year. She outlines depreciation rules (generally irrelevant unless UBIT/UDFI applies), defines prohibited transactions (credit extension, certain asset classes, and disqualified parties), and describes structuring personal funds alongside IRA funds via an ab initio multi-member IRA LLC with fixed ownership percentages. Finally, she explains UBTI for operating businesses and UDFI for debt-financed deals, noting trust tax brackets and that UDFI often compares favorably to investing outside an IRA.

00:00 How to use IRA LLC with Directed IRA

01:27 Tax Benefits & IRA LLC Basics

10:14 Prohibited Transactions

12:49 Partnering Personal Funds with IRA

17:59 UBTI & UDFI Explained

Directed IRA website

https://directedira.com/

Odin Capital Group Website 

https://odincapgroup.com/odin-capital-group-home

Self-Directed IRAs Explained: Rollovers, Fees, Real Estate Investing & Non-Recourse Loans (Inspira Financial)

In this CRE Deep Dive episode, Dennis interviews Chris Barnett of Inspira Financial about how to open and fund a self-directed IRA and use it to invest in real estate and other alternatives while still having access to traditional public securities in the same account. Chris explains the three-step process (open the account, move funds via rollover or transfer, then invest), typical timelines, and Inspira’s flat annual fee structure, including a $100 discount for Oden Capital investors, per-asset pricing with a cap, and limited additional wire fees. They cover rolling over TSP funds, partial rollovers, annual contribution limits, how the IRA is vested as the buyer and pays expenses through a portal, non-recourse loan rules, and how UBIT/UDFI can apply to debt-financed profits. The conversation also compares standard custody to checkbook-control IRA LLCs and solo 401(k)s.

00:00 How to get a Self-Directed IRA with Inspira Financial

00:27 Introduction

02:24 Opening an Account

04:05 Fee Structure

11:02 Buying Real Estate in an IRA

15:09 Non-Recourse Loans & UBIT

19:01 LLC & Solo 401k Options

Insipra Financial website https://inspirafinancial.com/

Chris Barnette

Business Development Manager

P: 630-348-8943

chris.barnette@inspirafinancial.com

ODIN CAPITAL GROUP WEBSITE

https://odincapgroup.com/odin-capital-group-home

Most investors think their retirement account is limited to stocks, bonds, and mutual funds.

What if your IRA could invest in real estate, private lending, syndications, private equity, and other alternative assets?

In this episode of CRE Deep Dive, Dennis Bamford sits down with Mandy Drysdale of IRA Club to discuss how self-directed retirement accounts work, what investors need to know about rollovers, Roth conversions, HSAs, checkbook IRAs, and the hidden opportunities available inside retirement plans.

Mandy shares practical insights on fee transparency, retirement account flexibility, investor education, and common misconceptions surrounding self-directed investing.

What You'll Learn

• What a self-directed IRA actually is
• How 401(k) rollovers work
• Traditional vs Roth IRA strategies
• How HSAs can become powerful investing vehicles
• The truth about checkbook IRAs
• Non-recourse loans explained
• Self-directed investing opportunities in real estate
• Common mistakes investors make

Chapters

[00:00] Introduction
[02:15] Mandy's background and journey
[07:45] What is a self-directed IRA?
[14:10] Old 401(k)s vs current employer plans
[22:05] Contribution limits and rollover rules
[28:30] Understanding IRA Club fees
[39:20] iFlip AI investing platform
[46:00] Retirement account options and HSAs
[53:15] Roth strategies and youth Roth IRAs
[57:00] Checkbook IRAs and compliance
[59:00] Final thoughts and special offer

Guest Spotlight

Mandy Drysdale combines a background in financial advising and education to help investors better understand retirement account strategies through IRA Club.

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Most investors think retirement accounts are limited to stocks, bonds, and mutual funds.

But what if your IRA could own real estate?

In this episode of CRE Deep Dive, Dennis Bamford sits down with Michelle Thomas of CNB Custody, one of the longest-standing alternative asset custodians in the country, to discuss how self-directed IRAs can be used for real estate investing.

Michelle shares how CNB Custody helps investors navigate self-directed retirement accounts, explains common compliance mistakes, and breaks down the rules surrounding prohibited transactions, checkbook LLCs, funding strategies, and non-recourse lending.

If you're interested in using retirement funds to invest in real estate, this episode provides a practical roadmap to understanding the opportunities and the pitfalls.

What You'll Learn

• What a self-directed IRA is
• How CNB Custody works with alternative assets
• Direct real estate ownership inside an IRA
• Checkbook LLC structures explained
• Common prohibited transactions
• SEP IRA contribution opportunities
• TSP and 401(k) rollover strategies
• Partnering multiple IRAs on one property
• Non-recourse loans and UDFI considerations

Chapters

[00:00] Introduction

[02:12] Michelle Thomas' Background

[04:30] The History of CNB Custody

[07:05] How CNB Custody Differs from Other Custodians

[09:00] Custody Fees Explained

[12:05] Funding a Self-Directed IRA

[15:30] SEP IRAs, TSPs & Rollovers

[18:00] Real Estate Investing Inside an IRA

[20:20] Prohibited Transactions Explained

[23:15] Checkbook LLC Structures

[25:50] Partnering Multiple IRAs

[27:00] Non-Recourse Loans & UDFI

[28:00] Final Advice for Investors

About CNB Custody

CNB Custody is a division of Community National Bank and has been providing alternative asset custody services for more than four decades. Their team specializes in helping investors hold alternative assets, including real estate, inside retirement accounts while maintaining compliance with IRS regulations.

Visit CNB Custody here: Click me!

Apply to Be a Guest

Booking Link here: Click me!

Most people don’t realize they can use retirement funds to invest in real estate, precious metals, and other alternative assets through a self-directed IRA.

In this episode of CRE Deep Dive, Dennis Bamford sits down with Brianna Mares from Gold Star Trust Company to break down how self-directed IRAs actually work, how rollovers happen, common fees, and what investors should know before getting started.

Whether you’re exploring retirement diversification, alternative investments, or simply trying to understand your options beyond traditional retirement accounts, this episode delivers a practical introduction to the world of SDIRAs.

What You’ll Learn

• How to roll over a 401(k) into a self-directed IRA
• The difference between standard and precious metals IRAs
• Real estate IRA basics
• Common self-directed IRA fees
• What prohibited transactions are
• How Gold Star Trust Company handles customer support
• Why investor education matters in alternative investing

Chapters

[00:00] Introduction
[00:42] What Is a Self-Directed IRA?
[02:01] How IRA Rollovers Work
[03:12] 401(k) Loans & Eligibility Questions
[04:40] Real Estate IRAs vs Checkbook LLCs
[06:05] Self-Directed IRA Fee Breakdown
[09:02] Precious Metals IRA Explained
[11:01] Investor Education & Due Diligence
[13:12] Customer Service & Account Support
[15:45] Final Thoughts

Want to share your side of the story? Book a Call here!

What if your retirement account could invest in real estate instead of just stocks and mutual funds?

In this episode of CRE Deep Dive, Dennis Bamford sits down with Paul Herbes from Equity Institutional Services to break down how self-directed IRAs, solo 401(k)s, HSAs, and other retirement vehicles can be used for alternative investments like real estate syndications, private equity, and direct property ownership.

Paul explains how investors are using retirement funds to diversify beyond traditional Wall Street products while maintaining tax advantages and long-term growth potential.

What you'll learn

• How self-directed IRAs actually work
• What investments are allowed (and prohibited)
• Checkbook IRAs and LLC structures
• HSA and education account investing
• Solo 401(k) contribution advantages
• Real estate investing timelines and funding mechanics
• IRA rollover strategies
• Custodian fees and investor support

Chapters

[00:00] Introduction to Self-Directed IRAs
[01:40] Why Most Investors Don’t Know This Exists
[04:10] What You Can and Cannot Invest In
[07:15] How Rollovers and Transfers Work
[10:20] Using HSAs and Education Accounts
[13:05] In-Service Rollovers Explained
[15:40] Real Estate Investing Timelines and Funding
[18:55] Checkbook IRAs and LLC Structures
[22:10] Solo 401(k)s and Contribution Limits
[24:00] Fee Structures and Investor Support
[25:35] Midland Trust and Final Thoughts

If you’ve ever wondered whether your retirement account could do more than sit in the stock market, this episode is a must-watch.

Apply to be a guest here: Click me!

What if your retirement account could invest in real estate instead of just stocks and mutual funds?

In this episode of CRE Deep Dive, Dennis Bamford sits down with Lindsay Merino from Directed IRA to break down how self-directed IRAs actually work for real estate investors.

They cover rollover timelines, IRA LLC structures, checkbook control, prohibited transactions, property management logistics, fees, and the biggest mistakes investors make when using retirement funds for alternative investments.

If you’ve heard terms like “IRA LLC,” “checkbook IRA,” or “self-directed Roth IRA” but never fully understood how they work, this episode gives a practical beginner-friendly overview.

What You’ll Learn:

• How long IRA rollovers actually take
• The difference between an IRA and IRA LLC structure
• How rental income flows through a self-directed IRA
• What prohibited transactions are
• Which family members your IRA cannot transact with
• How investors use retirement accounts for real estate
• Why education is critical when self-directing retirement funds

Chapters

[00:00] Intro to Self-Directed IRAs
[00:42] Rollover Timelines Explained
[03:02] IRA LLC vs Standard IRA Structure
[05:12] How Rental Income Flows Through an IRA LLC
[07:15] Directed IRA Fee Structure
[10:08] Setting Up an IRA LLC
[12:05] Foreign Investments & Cannabis Investments
[14:03] Prohibited Transactions Explained
[18:45] Directed IRA Education Resources
[20:15] Final Thoughts & Wrap Up

Special Guest:

Lindsay Merino at Directed IRA

Special Shoutout

Shoutout to Direct IRA for helping educate investors on self-directed retirement strategies.

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