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 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

[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

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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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 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

[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

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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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.

• 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

[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

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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.

• 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

[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.

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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.

• 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

[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

Lindsay Merino at Directed IRA

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

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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

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