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PODCAST

Real Estate Investing for Cash Flow with Kevin Bupp

There are a lot of real estate podcasts out there, most of which focusing on the residential fix and flips or wholesaling, but Kevin Bupp believes there"s a smarter way to build long term cash flow and generational wealth. On the Real Estate Investing For Cash Flow podcast, you"ll learn firsthand how the most successful commercial real estate investors in the world have learned to leverage their multifamily and commercial properties to create a steady stream of passive income. We"ll spend time with

business investing

All Episodes

31:09

Real Deals: We Created $15M in Value on This...

Real Estate Investing for Cash Flow with Kevin Bupp ·

2026/10/05

Some commercial real estate investments don’t look like obvious winners on the surface. Complexity, uncertainty, and unanswered questions scare many investors away, but they can also lead to some of the best opportunities. That was certainly the case with the deal I’m about to show you: a great asset, in a great location, with more than a few hurdles along the way.Today’s Sunrise Capital Investors case study involves a $33.2 million parking garage in Clearwater Beach, Florida. This was one of

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52:04

When We Say “No” to a Great Deal (Even If It Fits Our...

Real Estate Investing for Cash Flow with Kevin Bupp ·

2026/09/29

Commercial real estate acquisitions doesn't simply mean finding a deal, underwriting it, and hoping for the best. Often, having the discipline to act on what you find will make you wealthier than even the greatest properties you could buy. Every investment has skeletons in the closet, and even if the problems you inevitably uncover are fixable, some just aren’t worth fixing. So when do you draw the line even after you’ve fallen in love with the deal?Today, I’m speaking to my partner and CEO of

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41:30

These “Durable” Commercial Real Estate Investments...

Real Estate Investing for Cash Flow with Kevin Bupp ·

2026/09/21

What separates a piece of commercial real estate that doesn’t survive from one that endures for decades—and through multiple market cycles? It’s a question Ed Pitoniak, founder and CEO of VICI Properties, has spent the last several years working to answer.Today, Ed leads one of the nation’s largest owners of experiential commercial real estate. But he took an unconventional path to get there, starting at a ski publication before moving into hospitality and, eventually, real estate. Along the way,

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51:18

He Walked Away Mid-Deal. It Cost Him $100,000 (But...

Real Estate Investing for Cash Flow with Kevin Bupp ·

2026/09/14

Real estate investing demands conviction, but when market conditions shift—sometimes even mid-deal—do you stick to your guns or walk away?August Biniaz, CIO and co-founder of CPI Capital, found himself toeing this exact line shortly after underwriting and raising capital for a large, build-to-rent community in Tucson, Arizona. When interest rates spiked, the deal no longer penciled, but exiting meant sacrificing significant time and over $100,000 in sweat equity. On the other hand, moving

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45:09

99% Passed on These Commercial Properties. They Made...

Real Estate Investing for Cash Flow with Kevin Bupp ·

2026/09/07

After more than 50 years in commercial real estate, Bill Cummings has built an 11-million-square-foot portfolio spanning 12 communities around Greater Boston. But he did so by ignoring many of the conventional rules of real estate investing.When his peers suggested he explore new markets, he stayed local. When others urged him to sell, he continued to hold for decades. And when other developers steered clear of neglected buildings, Bill saw opportunity, transforming overlooked properties for

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56:08

He Tripled His Cash Flow by Doing What Most...

Real Estate Investing for Cash Flow with Kevin Bupp ·

2026/08/31

Early on, most real estate investors are chasing the same thing: more. More properties. More units. More cash flow. But eventually, “more” becomes a trap.Every acquisition brings new challenges and risks. At some point, the smartest move isn’t buying more. It’s pruning. Chris Lopez, co-founder of Property Llama and host of the PassivePockets podcast, argues that investors should act more like fund managers by routinely reassessing, rebalancing, and reprioritizing their investments. Because

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51:40

How to Earn a 13%-18% Average Annual Return in 2026...

Real Estate Investing for Cash Flow with Kevin Bupp ·

2026/08/24

Tax liens are often pitched as a passive way to earn double-digit returns from investments that are backed by real estate.This is only half true. While these investments average 13%-18% annual returns, they may actually be one of the least passive investing strategies. With roughly 20 years of experience as a real estate investor, attorney, and title professional, Stephen Morel understands all that this strategy entails better than most. The truth is that most investors are thinking

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23:27

Real Deals: 15% Above Projections on a “Risky” Deal...

Real Estate Investing for Cash Flow with Kevin Bupp ·

2026/07/27

One of the biggest mistakes investors make is confusing uncertainty with risk. When a deal looks “messy,” most operators walk away. They treat temporary problems as if they’re permanent and, in the process, overlook some of the greatest investing opportunities.Today, I’m bringing you another Sunrise Capital Investors case study: the Meadows of North Lewisburg and South Towne Meadows, a pair of manufactured housing communities roughly 30 minutes outside downtown Columbus, Ohio. On the surface, this

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52:43

What $100M Institutional Investors Look for Before...

Real Estate Investing for Cash Flow with Kevin Bupp ·

2026/06/15

Many real estate operators assume institutional capital is simply retail capital at a larger scale: fewer investors, bigger checks.It’s not. What they’re missing is that institutional capital often requires you to build more infrastructure, create tighter procedures, and relinquish some control of the asset itself. The question is: Is the consolidation you get from institutional capital worth all the extra effort? If you ask John Azar, founder and CEO at Peak 15 Capital, it depends. For the

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35:22

Top U.S. Universities Have a $1T Real Estate...

Real Estate Investing for Cash Flow with Kevin Bupp ·

2026/06/09

Most investors chase opportunities in familiar asset classes like multifamily, self-storage, or mobile home parks, but today’s guest has carved out a narrow lane within the industry: university-aligned real estate investing.America’s top universities are facing a $1 trillion infrastructure problem over the next decade, and to continue attracting top talent, they need upgraded facilities and amenities. Josh Parker, founder, chairman, and CEO of Ancora, has built a business that collaborates with

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36:10

Real Deals: The Biggest Mobile Home Community We’ve...

Real Estate Investing for Cash Flow with Kevin Bupp ·

2026/06/01

No matter how much you underwrite, budget, plan, and strategize, nothing ever goes exactly to plan. On our biggest mobile home park investment yet (700+ lots), we thought we had accounted for every obstacle that could have been thrown our way—boy, were we wrong. But with the right team, tactics, and pivots, we turned what many would have given up on into a property with close to $3M in annual NOI—and even more room to grow.Welcome back to another case study episode, where I’m sharing real

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32:50

The “Captive Insurance” for Landlords That Pays You...

Real Estate Investing for Cash Flow with Kevin Bupp ·

2026/05/25

Landlord insurance has slowly become a major cost for many operators. After 2020, insurance prices began to rise rapidly, and making a claim became even harder when disaster struck. For many operators, it feels like throwing tens of thousands, if not hundreds of thousands of dollars, into the furnace every year, for a benefit you’ll rarely use. And who stands to profit from it? Insurance companies. But an overlooked insurance structure is becoming increasingly common among operators, saving them

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38:06

Private Air Travel Is Coming: But the “Smart”...

Real Estate Investing for Cash Flow with Kevin Bupp ·

2026/05/11

When new technology emerges, the biggest winners aren’t the headline watchers or the reluctant investors. Rather, it’s those who already control the infrastructure when that technology becomes mainstream who profit most.The next major infrastructure wave? Advanced air mobility. It’s not a matter of if, but when private aircraft become the next popular mode of travel in the United States, and Lisa Wright, founder of Landings, will be waiting at the runway when it arrives. With decades of

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41:40

From Zero to 1,200+ Multifamily Units in 7 Years...

Real Estate Investing for Cash Flow with Kevin Bupp ·

2026/05/04

Many investors talk about financial freedom, but few ever scale to the point where they can leave their W-2 jobs and live off the cash flow from their real estate investments.Jason Kenney did it. Completely burned out after two decades of climbing the corporate ladder, Jason and his wife started allocating their W-2 income to real estate assets with the goal of buying back their time. Within only a few years, Jason was able to quit his W-2 job and replace his income with cash-flowing

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20:21

Real Deals: A $10M Win by Taking on This “Complex”...

Real Estate Investing for Cash Flow with Kevin Bupp ·

2026/04/27

This single property created more than $10M in value, but it was the most complex real estate deal we’ve ever done. We had to put a million dollars at risk to even start the transaction—and it was non-refundable. Multiple buyers, a cross-collateralized property in receivership with a parking lot, a hotel, and office space. This wasn’t going to be easy, but it definitely paid off. Today, I’m peeling back the curtain, showing you the full numbers and story of this commercial real estate case

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49:28

Operational “Landmines” That Will Wipe Out Your...

Real Estate Investing for Cash Flow with Kevin Bupp ·

2026/04/06

Mobile home parks are often labeled “recession-proof,” and it’s largely true. They were some of the most resilient assets throughout the Great Financial Crisis, when single-family homes, multifamily apartments, and most other asset classes saw deep distress.But what is it about mobile home parks that make them seemingly “safe,” and is there a catch? Jack Martin, co-founder and CIO of 52TEN, was investing in real estate before, during, and after the 2008 housing market crash, and the fallout

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41:43

The Passive Investing “Traps” Most Limited Partners...

Real Estate Investing for Cash Flow with Kevin Bupp ·

2026/03/30

Over the last few years, many real estate investors learned a painful lesson: a polished pitch deck and impressive projections don’t guarantee a “safe” investment. Deals went south, capital got stuck, and naturally, passive investors are now far more cautious about where they deploy their hard-earned money.Sarah Miskelly, founder of Hylee Capital, has witnessed this shift firsthand. Today, smart limited partners are no longer chasing flashy pro formas. They want risk-mitigated, institutional-grade

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33:39

Value-Add Multifamily: Risks, Opportunities, & “Deep”...

Real Estate Investing for Cash Flow with Kevin Bupp ·

2026/03/23

In multifamily real estate, it used to be that “a rising tide lifts all boats.” In this market cycle, that’s no longer the case. Apartment deals aren’t profitable by luck. They’re run by disciplined operators who understand the difference between surface-level updates and deep, value-add strategies that drive tenant retention, rent growth, and higher returns.After starting his career as an architect, Mark Shuler transitioned into ownership and development, and today, he leads a private equity firm

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48:29

$250,000/Year Cash Flow from One “Small” Commercial...

Real Estate Investing for Cash Flow with Kevin Bupp ·

2026/03/16

Imagine replacing an entire rental property portfolio with just one “small” commercial asset. You can either manage 80+ rental units or just one building, with a fraction of the tenants, turnover, and headaches.Saul Zenkevicius did just that. He netted $250,000/year in cash flow from one small bay industrial real estate deal which quickly replaced the entire cash flow from a rental property portfolio he’d built over the years. These small bay properties still have strong demand in most markets,

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37:55

What Really Drives Cash Flow in Mobile Home Parks...

Real Estate Investing for Cash Flow with Kevin Bupp ·

2026/03/09

Building wealth through mobile home park investing is much less about timing the market or finding the “perfect” deal and far more about operating with precision, discipline, and a long-term vision. Too often, solid acquisitions are undermined by a series of avoidable missteps, not because the opportunity was flawed, but because operations were.Few understand this better than Brad Johnson, co-founder of Vintage Capital, who has closed more than $3 billion in acquisitions to date. Across 20-plus

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