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Real Estate Investing for Cash Flow with Kevin Bupp

Real Estate Investing for Cash Flow with Kevin Bupp

Kevin Bupp 998 Episodes Jun 15, 2026

This podcast focuses on commercial real estate investing for cash flow and generational wealth, moving beyond residential fix-and-flips. Host Kevin Bupp interviews industry experts on topics like multifamily apartments, syndication, and passive income. The show aims to help both new and experienced investors scale their real estate businesses.

Episodes

What $100M Institutional Investors Look for Before Cutting the Check | Ep. 992 Jun 15, 2026 3163 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
Top U.S. Universities Have a $1T Real Estate “Problem” (And He’s Solving It) Jun 9, 2026 2122 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 amen
Real Deals: The Biggest Mobile Home Community We’ve Ever Bought Jun 1, 2026 2170 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—
The “Captive Insurance” for Landlords That Pays You to Protect Your Property May 25, 2026 1970 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
Don’t Get Wiped Out: The Multifamily Investing Strategy That Beat 3 Downturns | Ep. 988 May 18, 2026 2334 What do the 2000 dot-com crash, the 2008 Great Financial Crisis, and the 2022 interest rate shock have in common? They wiped many multifamily operators out. Dwight Dunton survived all three. As founder and CEO of Bonaventure, Dwight and his team are responsible for $2.8 billion in assets under management (AUM). But Dwight didn’t start a fund, raise capital, and figure it out as he went. He learn
Private Air Travel Is Coming: But the “Smart” Investing Play Is on the Ground | Ep. 987 May 11, 2026 2286 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 Lis
From Zero to 1,200+ Multifamily Units in 7 Years (Replacing His W2 Income) | Ep. 986 May 4, 2026 2500 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 onl
Real Deals: A $10M Win by Taking on This “Complex” Parking Garage Deal Apr 27, 2026 1221 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 p
Developing a $140M “Passion Project” to Turn Dirt Into a Community Dream Apr 20, 2026 2708 For many real estate investors, development is the next level of property investing. Instead of renovating, you’re building from the ground up, turning dirt into something hundreds or even thousands of people will use daily. But how do you start, get in good graces with the local government, and build projects you can be truly proud of? Kristi Kandel went from zero development experience to ru
Senior Housing’s Inflection Point: Demand is Quickly Outpacing Supply Apr 13, 2026 3030 Senior living investments are at a critical inflection point. Demand is sharply rising as the Baby Boomer generation ages, but supply hasn’t kept pace. The “silver tsunami” is starting to send waves our way, and skilled operators are already taking advantage. Value-add senior living investments, like the example shared by today’s guest, are seeing values multiply—and diligent operators have huge o
Operational “Landmines” That Will Wipe Out Your Mobile Home Park Cash Flow Apr 6, 2026 2968 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
The Passive Investing “Traps” Most Limited Partners Never See Coming Mar 30, 2026 2503 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

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