Cash Flow Connections - Real Estate Podcast

Latest Episodes:

Leveraging Preferred Equity for Smarter Deals - E1127 - RMR Aug 29, 2025

Show notes

In today’s RaiseMasters Radio episode, Adam is joined by Jeff Flynn of Aspen Ridge Capital to discuss his journey from Navy service to building a portfolio of mobile home parks across the Southeast.

We dive into his creative approach to capital raising, including how he turned sellers into investors, and the lessons he’s applying to scale his business.

Tune in to hear how Jeff is structuring deals, growing his investor base, and building communities through mobile home park investing.

Resources mentioned in the episode:

Jeff Flynn

Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge.

Learn more here: https://raisingcapital.com/cre

How Obsession Turned Hunter Thompson Into A Capital-Raising POWERHOUSE - E1126 - CFC Aug 28, 2025

Show notes

Most people are scared of obsession…
But for me, it’s been the single greatest driver of success.

In this special episode—originally recorded with Ben Reinberg on his show I Own It—I unpack how obsession with my mission reshaped my life, business, and wealth.

We talk about everything:

What really fuels confidence when raising equity
How a poker boom shaped my capital-raising philosophy
Why your story is the most powerful tool you’ve got
The secret mental shift that helped one of my students raise millions
And how to build investor trust—without a “perfect” background

If you’ve ever struggled with self-doubt, imposter syndrome, or the fear of calling your shot…
This one’s for you.

Talk soon,
Hunter Thompson

Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge.

Learn more here: https://raisingcapital.com/cre

From The Archive: Navigating Distress: Opportunities in Multifamily and the Road Ahead - E1125 - TT Aug 26, 2025

Show notes

In this Topical Tuesday episode, I spoke with Brian Burke who is the President & CEO of Praxis Capital, Inc. Brian has acquired over 800 million dollars’ worth of real estate over a 30-year career including over 4,000 multifamily units and more than 700 single-family homes. He is also the author of “The Hands-Off Investor: An Insider’s Guide to Investing in Passive Real Estate Syndications”.

Be sure to tune in if you’re interested in learning about:

The rise in distress across different lending sectors, with CMBS loans seeing notable increases.
Regional multifamily opportunities, highlighting short-term potential in the Midwest and long-term value in the Sunbelt.
The challenges and evolving strategies in value-add multifamily investing.
Insights on vertical integration in property management and its complexities.

To your success,

Tyler Lyons

Resources mentioned in the episode:

Brian Burke

Website

Instagram

Book

Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge.

Learn more here: https://raisingcapital.com/cre

One Way To Provide More Cash Flow To Multifamily Investors - E1124 - MM Aug 25, 2025

Show notes

In today’s Monday Minutes episode, I break down the reality of cash flow in today’s private equity and multifamily markets, and share how we’re structuring deals to compete with bonds yielding over 4%.

I also walk through a new share class we’ve introduced at Asym Capital that offers an 8% current pay with a 5% kicker on the backend—an approach designed to meet investor cash flow needs while still keeping the upside.

Tune in to hear how this structure works and how you might apply it to your own deals.

Resources mentioned in the episode:

Asym Capital

Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge.

Learn more here: https://raisingcapital.com/cre

Why Partnerships Are Key to Capital Raising Success - E1123 - RMR Aug 22, 2025

Show notes

In today’s RaiseMasters Radio episode, Adam is joined by Lee Yoder to talk about his journey from physical therapist to managing nearly 900 units in the Midwest.

They dive into his recent $8.25M raise for a 415-unit portfolio, the role of partnerships in scaling quickly, and why focusing on tertiary markets has been a game-changer.

Tune in to hear how Lee is building cash flow, momentum, and lasting investor relationships.

Resources mentioned in the episode:

Lee Yoder

Website

Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge.

Learn more here: https://raisingcapital.com/cre

How To Structure TOUGH Deals - E1122 - CFC Aug 21, 2025

Show notes

Most investors say they want “complex deals with upside.”

But the truth is…

When things really get messy—most people run.

That’s why I sat down with Kevin Bupp, co-founder of Sunrise Capital Investors, who’s made a career out of structuring deals that others wouldn’t even touch.

I’m talking about:

Cross-collateralized assets in special servicing
Simultaneous closings across parking, office, and hotels
Carving out value in the middle of institutional chaos

In today’s episode, Kevin reveals the exact playbook he used to pull off one of the most complex deals I’ve ever seen… and how that one deal opened the door to institutional partnerships that changed everything.

We break down:

Why complex = high ROI (if you have the right team)
How to buy from institutions—even if you’re a small firm
Why boring assets like parking
lots are actually cash flow gold
How to turn distress into massive opportunity

If you want to learn how the best operators actually structure tough deals…

Listen to the episode now.

Take Control,
Hunter Thompson

Resources mentioned in the episode:

Kevin Bupp

Website

Podcast

Instagram

Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge.

Learn more here: https://raisingcapital.com/cre

Building Smarter LP Strategies - E1121 - TT Aug 19, 2025

Show notes

In this Topical Tuesday episode, I spoke with Leyla Kunimoto who is the co-founder of Accredited Investor Insights, which is a platform created to bridge the information gap for high net worth investors. She's focused on delivering objective education and insights to help accredited investors make more informed decisions across both private and public markets.

Be sure to tune in if you’re interested in learning about:

Leyla’s journey from finance and consulting to becoming a full-time LP investor.
Practical tips on vetting sponsors and deals—what green flags to look for and the red flags that save time early.
The real work behind “passive” investing, misconceptions LPs often face, and why diversification is trickier than it seems.
How AI tools can sharpen due diligence, generate better questions, and help investors avoid costly mistakes.

To your success,

Tyler Lyons

Resources mentioned in the episode:

Leyla Kunimoto

Substack

Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge.

Learn more here: https://raisingcapital.com/cre

When Should You FIRE A Fund Manager? - E1120 - MM Aug 18, 2025

Show notes

In today’s Monday Minutes episode, I dive into the rise of Fund of Funds structures in real estate—and the challenges operators face when partnering with inexperienced fund managers.

From compliance risks to brand protection, I share strategies for navigating these relationships without losing your edge.

Tune in to learn how to maximize the upside while avoiding costly mistakes.

Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge.

Learn more here: https://raisingcapital.com/cre

How to Keep Investors Engaged in Any Market Cycle - E1119 - RMR Aug 15, 2025

Show notes

In today’s RaiseMasters Radio episode, Adam is joined by Stewart Heath to discuss his journey from CPA and C-level executive to raising capital for “boring” but powerful cash-flowing commercial real estate deals.

We talk about the importance of consistent investor communication, lessons learned during challenging capital-raising periods, and how to build a strong portfolio foundation with stabilized assets.

Tune in to hear how Stuart is helping investors generate reliable income while creating opportunities for collaboration within the RaiseMasters community.

Resources mentioned in the episode:

Stewart Heath

Website

Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge.

Learn more here: https://raisingcapital.com/cre

Important Updates With Self-Directed Retirement Accounts - E1118 - CFC Aug 14, 2025

Show notes

Most investors know what an IRA is…

But almost no one knows what it can really do.

In fact, there’s a little-known type of retirement account that’s been legal for 50 years…

…yet most investors still don’t even realize it exists.

Today, I sat down with Kaaren Hall — founder of UDirect IRA and author of The BiggerPockets Guide to Self-Directed IRA Investing, to set the record straight.

She explains how this one strategy can unlock trillions in sidelined capital…

And help you raise money for your next deal — without Wall Street.

In today’s interview, she breaks down:

Why 50 years of misinformation has kept investors in the dark
The SECURE Act 2.0 rule that could let you contribute $70,000 after-tax into a Roth-style account
Why syndications are the #1 asset self-directed IRAs invest in
The one mistake that can make your self-directed IRA taxable
What the “25% ERISA Rule” means for fund-of-fund managers
How to avoid UDFI with the right structure
The rising trend of crypto in retirement accounts

Plus, we cover exactly how capital calls work inside IRAs, how the rules change once you hire employees, and why more 401k plans may soon include alternative assets…

If you want to tap into the $14 trillion IRA market and protect your investors from painful tax mistakes…

Listen to the episode now.

Take Control,
Hunter Thompson

Resources mentioned in the episode: