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CRE Deep Dive is a commercial real estate podcast focused on bridging the gap between self-directed retirement capital and real investment opportunities.
Hosted by Dennis Bamford, the show explores how investors, custodians, and advisors are using self-directed IRAs to access and fund commercial real estate deals. Each episode breaks down how capital actually flows: from 401k rollovers into SDIRAs, into real assets like apartment syndications and private placements.
Rather than surface-level education, the conversations focus on real execution: how deals are structured, how investors participate, what custodians require, and where people get stuck or make costly mistakes.
By connecting both sides of the equation, those who control capital and those who deploy it: CRE Deep Dive gives listeners a clear, practical path to putting retirement funds to work in commercial real estate.
This podcast is built for investors, advisors, and professionals who want more control over their capital and a smarter way to participate in real estate beyond traditional markets.
CRE Deep Dive connects self-directed retirement capital with real commercial real estate deals, showing investors how to actually put their money to work.
Episodes
15 hours ago
15 hours ago
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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Wednesday Jun 24, 2026
Wednesday Jun 24, 2026
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.
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Wednesday Jun 17, 2026
Wednesday Jun 17, 2026
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!
Wednesday Jun 10, 2026
Wednesday Jun 10, 2026
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!
Wednesday Jun 03, 2026
Wednesday Jun 03, 2026
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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Wednesday May 20, 2026
Wednesday May 20, 2026
Most people don’t even realize they can invest their retirement funds outside the stock market.
In this episode of CRE Deep Drive, Dennis Bamford sits down with Matt Moore from CamaPlan to break down how self-directed IRAs actually work and how investors are using them to access real estate, private deals, and alternative investments.
From rollovers and funding strategies to IRS rules and prohibited transactions, this conversation gives you a clear, practical understanding of what’s possible (and what to avoid).
What You’ll Learn:
- What a self-directed IRA is and how it works
- How to roll over funds from a 401k or IRA
- The biggest IRS rules and prohibited transactions
- How real estate investing works inside an IRA
- Passive vs active investing strategies
- How fees compare to traditional advisors
Timestamps:
[00:00] Introduction
[02:30] What is a self-directed IRA?
[06:45] How to fund your IRA (rollovers & transfers)
[12:10] IRS rules and penalties explained
[18:20] Can you use loans or cash inside an IRA?
[25:40] Fees and cost structure
[31:15] Prohibited transactions explained
[40:10] Real estate investing inside an IRA
[46:30] Passive vs active investing strategies
[52:00] Final thoughts and resources
CTA:
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