Real Estate Investing for Cash Flow with Kevin Bupp - podcast cover

Real Estate Investing for Cash Flow with Kevin Bupp

Kevin Buppwww.kevinbupp.com
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 industry experts who will teach you how to take your Real Estate Investing business to the next level. Whether you're a brand new Real Estate investor or someone who's looking to make the transition into bigger and more profitable deals, this is the show for you. This is where the BIG BOY RE Investors come to play...ARE YOU READY? On our show, we'll feature industry experts and discuss topics such as: * Commercial Real Estate Investing * How to get started * Creating Passive Income from CRE * Syndication * Retail Shopping Centers * Mobile Home Parks * Medical Office * Multifamily Apartments * Industrial * Office * Self Storage * Industrial * 1031 exchanges * Development * Investing via your self directed IRA * Private Lending * How to buy your first commercial property * And much, much , more
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Episodes

What $100M Institutional Investors Look for Before Cutting the Check | Ep. 992

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 ...

Jun 15, 202653 minEp. 992

Top U.S. Universities Have a $1T Real Estate “Problem” (And He’s Solving It)

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 ...

Jun 09, 202635 minEp. 991

Real Deals: The Biggest Mobile Home Community We’ve Ever Bought

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 deal...

Jun 01, 202636 minEp. 990

The “Captive Insurance” for Landlords That Pays You to Protect Your Property

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 the...

May 25, 202633 minEp. 989

Don’t Get Wiped Out: The Multifamily Investing Strategy That Beat 3 Downturns | Ep. 988

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 learned to grow and protect his own money first. At just 25 years old , while his peers chased flashy i...

May 18, 202639 minEp. 988

Private Air Travel Is Coming: But the “Smart” Investing Play Is on the Ground | Ep. 987

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 experi...

May 11, 202638 minEp. 987

From Zero to 1,200+ Multifamily Units in 7 Years (Replacing His W2 Income) | Ep. 986

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 invest...

May 04, 202642 minEp. 986

Real Deals: A $10M Win by Taking on This “Complex” Parking Garage Deal

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 st...

Apr 27, 202620 minEp. 985

Developing a $140M “Passion Project” to Turn Dirt Into a Community Dream

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 running her own office in a year , with undeniable success. She built 30 Family Dollar locations in one ...

Apr 20, 202645 minEp. 984

Senior Housing’s Inflection Point: Demand is Quickly Outpacing Supply

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 opportunities not only to make sizable returns but also to provide better lives for their residents ...

Apr 13, 202651 minEp. 983

Operational “Landmines” That Will Wipe Out Your Mobile Home Park Cash Flow

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 fallou...

Apr 06, 202649 minEp. 982

The Passive Investing “Traps” Most Limited Partners Never See Coming

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-...

Mar 30, 202642 minEp. 981

Value-Add Multifamily: Risks, Opportunities, & “Deep” Upgrades That Drive NOI

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...

Mar 23, 202634 minEp. 980

$250,000/Year Cash Flow from One “Small” Commercial Property | Ep. 979

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...

Mar 16, 202648 minEp. 979

What Really Drives Cash Flow in Mobile Home Parks (After $3B in Acquisitions) | Ep. 978

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-...

Mar 09, 202638 minEp. 978

Investing in Parking Lots: Real Estate’s #1 Overlooked Opportunity | Ep. 977

Most people have never met anyone who invests in parking lots , let alone considered buying one themselves. Are investors looking past one of the most misunderstood opportunities of 2026? Yes. Today, I'm making the case for why parking lots deserve a serious look from every real estate investor. Imagine this: day-one cash flow , appreciation in the country’s best locations, dynamic pricing that can maximize revenue minute-by-minute , limited supply , growing demand . That’s the formula that ever...

Mar 02, 202629 minEp. 977

This Is What Makes Your Property Profitable (From Someone Who Owns 1,000+ Units)

Two overlooked “levers” helped Kent Ritter scale past 1,000 multifamily units —and most operators have never even thought of them. One helps you keep tenant turnover low, slashes your CapEx costs by 30% , and keeps your cash flow flowing. The other allows you to build properties for cheaper , do less capital raising, and get on the local government’s good side. Even if you’ve heard of these tactics, you probably haven’t tried them. Today, Kent Ritter from Hudson Investing discusses two strategie...

Feb 23, 202641 minEp. 976

3,500 Mobile Home Units and How to “Manufacture” Cash Flow

With 3,500 mobile home units under management, Andrew Keel is an expert at “forcing” value and “manufacturing” cash flow even from underperforming assets. He’s so dedicated to making each mobile home park investment work that he’s even lived on-site (with his family) to ensure value is being added from the second he closes. Through infill , diligent operations , and crucial fixed-rate debt , Andrew has been able to grow his portfolio at a time when many operators are forced to give up theirs. Th...

Feb 16, 202634 minEp. 975

How to Create Six-Figure Write-Offs on Each New Property (Cost Seg Explained)

This could be one of the highest ROI strategies in real estate , yet most investors ignore it. Imagine getting hundreds of thousands of dollars in write-offs , saving tens of thousands in taxes, all while you own income-producing, equity-building real estate . Most investors think they know what we’re talking about in today’s show, but if they did, they’d be jumping at the chance to use it. It’s no secret— cost segregation studies can become one of the most profitable weapons in your real estate...

Feb 09, 202642 minEp. 974

Buy the Dip (Without Getting Burned): How to Vet Sponsors Before Writing a Check

Everyone plans to “buy the dip” until it’s time to write the check. Multifamily opportunities are rising , and with properties 20%+ off the peak of pricing , investors are getting flooded with “deals.” But, like we learned over the past five years, the wrong sponsor (even with the right deal) can kill your returns and blow up the wealth you spent so long to build. So, how do you spot the opportunities vs. the landmines in multifamily? We brought on fund of funds manager, Lon Welsh , to share his...

Feb 02, 202628 minEp. 973

CRE’s “Buy of the Decade” Is Cheaper Than Ever w/Bull Realty CEO

This could be commercial real estate’s “buy of the decade,” according to a 35-year investing veteran . This asset class is seeing rock-bottom prices, shrinking supply, and acquisitions at a quarter of replacement cost. Everyone says this asset is dead, so why are expert investors, lenders, and brokers betting on it? Michael Bull , founder & CEO of Bull Realty, Inc., has personally overseen over $8 billion in commercial real estate transactions in his 35 years in the industry. He’s seeing sen...

Jan 26, 202636 minEp. 972

The REIT-Ready Blueprint for Building a Class-A (Cash-Flowing) Storage Facility

Just over five years ago, express car washes were peaking. Private equity was getting in, ready to buy up these cash-flowing projects at high prices. At this moment, Ben Salzberg and Bill Kanatas knew it was time to get out and pivot toward an even more durable asset . What did they turn to? Self-storage , and not your average mom-and-pop shop. Class-A, climate-controlled , multi-story facilities that self-storage REITs could easily come in and run . It’s a blueprint that has worked for them for...

Jan 19, 202634 minEp. 971

Hidden NOI: How Design and Data Quietly Add $100K+ to Your Bottom Line

Every multifamily operator wants to know how to increase NOI , but they’re not doing it the right way. Traditional renovations leading to rent increases have been harder to get right in the past few years. But what if there was a “hidden” source of not only higher revenue but also lower expenses —something 99% of operators are unaware of, that could increase NOI by tens of thousands per month. Today, Bill Douglas of OpticWise ( https://www.opticwise.com/ ) and Marcy Sagel of MSA Interiors ( http...

Jan 12, 202649 minEp. 970

Raised in a Trailer Park. Now He Owns Them. w/Brian Spear

What does it take to go from growing up in a mobile home…to owning hundreds of mobile home lots across the country? Today’s guest, my business partner Brian Spear , is living proof that mindset and mission matter more than where you start. In this episode, Brian shares his remarkable journey into mobile home park investing , the lessons from the wealthy that helped him build long-term success, and how we joined forces to build Sunrise Capital Investors —with mobile home park investments totaling...

Jan 05, 202654 minEp. 969

When Deals Fall Apart: CRE’s Go-to Lawyer on Navigating Lender Landmines w/Richard Crouch

More syndications are going sideways . Capital calls have become common. Tensions are rising between operators and investors…but not for all deals. If you had talked to today’s guest before forming your real estate syndication, there’s a good chance you’d already have a battle plan for every potential challenge . Thankfully, today, CRE’s go-to legal advisor is sharing his take for free. Richard Crouch has worked on eight figure commercial real estate deals for over two decades, helping advise on...

Dec 29, 202529 minEp. 968

How We Bought $80M of Real Estate This Year + Huge Announcement

2025 is about to be in the books , and for many real estate investors, it was a challenging year. But at Sunrise Capital , it’s been a year of massive growth , disciplined pivots , and, for me, purpose : my wife and two sons. We’ve acquired $80,000,000 in new assets this year— irreplaceable real estate that we couldn’t pass up. We’ve had to step away from other deals when the numbers didn’t pencil, and in the end, we’re monumentally proud of what we’ve accomplished. So what’s next? I have a big ...

Dec 22, 202525 minEp. 967

The Painful Failure That Pushed Me to Pivot (and Made Me Millions) w/Joe Downs

The fear of failure stops many from ever getting into real estate. But what if it's the failures that actually make you wealthy? Today's guest woke up in his 30s, broke and burned out, having traded years of his life for a business that went belly up. What looked like a failure to everyone else was the start of a multimillion-dollar business empire for Joe Downs. Joe has invested in it all—rental properties, flips, self-storage, mortgage notes, industrial warehouses, and more—but his newest obse...

Dec 15, 202540 minEp. 966

Skip the Sunbelt: Why "Micropolitan" Multifamily Markets are Unbeatable w/Cory Jacobson

While most operators chase the Sunbelt states, one overlooked market type is making small- and mid-sized multifamily investors wealthier. It's got near-zero vacancy, with strong employment anchors, and durable cash flow thanks to consistent demand. They're not big cities; instead, they're what today's guest calls "micropolitan" areas—top multifamily markets even the most experienced investors overlook. While making just $35,000 per year, Cory Jacobson made the best move a small investor can make...

Dec 08, 202548 minEp. 965

The Opportunity You've Never Heard of in CRE ("IOS" Real Estate)

This could be one of the, if not the, most under realized opportunities in commercial real estate. It's a blue ocean market operating in a boring business space that most investors (and service providers) are completely overlooking. But, Jake Guso tapped into what no other real estate investor knew about industrial outdoor storage management, specifically truck parking lot businesses. These mom-and-pop shops are running almost entirely on handwritten notes and Zelle payments and it's an absolute...

Dec 01, 202532 minEp. 964

The Most Underrated Metric in Multifamily (Not Cap Rate/Cash Flow) w/Joe Root

One key metric could tell you immediately whether a multifamily real estate investment is worth buying—but most people ignore it. It's not cash flow, it's not cap rate, and it's probably something you've overlooked dozens of times. Joe Root helped grow his family's multifamily portfolio and manages over 100 properties using this metric. Joe left the glitz of a corporate Wall Street career when he realized his family's apartment portfolio was better than the big city life. Multifamily management ...

Nov 24, 202541 minEp. 963
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