Real Estate Investing for Cash Flow with Kevin Bupp

The real estate investors who are thriving in today’s market are the ones who ignored the pressure to buy questionable deals during the boom years. While many operators fell for floating-rate debt, banked on unrealistic rent growth, and underwrote for best-case scenarios, a more “patient” group focused on the fundamentals. Hannah Hammond, founder and CEO of the capital advisory firm and commercial...

Real estate has arguably been the largest wealth generator in history, but for many years, most opportunities have been out of reach for those without large bank accounts. Alex Blackwood is on a mission to change that with fractional real estate. While working at Goldman Sachs’ private equity group and delivering 15%-20% annual returns to investors, he started dreaming of a company that would lowe...

Industrial real estate might look simple from the outside. You buy a large box, lease it out, and collect rent. But like with any asset, you can lose your shirt just as easily as you can make a fortune. Joel Friedland, founder of Brit Properties, understands this better than most. Two years ago, he and his team were bracing for another industry lull, largely driven by high interest rates and slugg...

Before you check out episode 993, get up to speed with Building a Resilient Industrial Portfolio: Lessons from Joel Friedland. In this episode, Joel Friedland, founder of Brit Properties and seasoned industrial real estate operator, shares his journey of transforming his investment philosophy after the lessons learned from the 2008 financial crisis. Discover how a focus on risk control, no debt st...

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...

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 ameni...

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—...

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...

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...

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...

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...

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 peeli...

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 runnin...

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...

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 i...

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...

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 archit...

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 portf...

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-fou...

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...

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,...

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...

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 s...

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 opportunit...

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 b...