Real Estate Investing for Cash Flow with Kevin Bupp

Providing affordable housing and making a profit don’t have to be mutually exclusive. One small real estate business has found a way to deliver brand-new homes in a lower price range and generate sizable margins.

Using land home packages, Chris Gavre and his partner build and sell roughly 50-60 homes per year while also addressing the affordable housing problem in his market of Greenville, South Carolina. The strategy is simple: buy and prepare an empty lot, install a manufactured house, and sell it for a sizable profit. Despite each project taking only 45-60 days to...

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 the most complex projects we’ve ever taken on, but through conservat...

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 Sunrise Capital Investors, Brian Spear. We sta...

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, he forged the skills and perspective needed to navigat...

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 forward meant potentially putting investor capital, and their reputation, at risk.

Rather than ra...

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 enormous profits.

This contrarian approach hasn’t just helped shape the culture at Cummings Properties; it’s also c...

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 the “buy and hold” strategy has a potentially dangerous blind spot: not enough investors consider the exit, or wheth...

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 about these investments the wrong way. Tax liens aren’t a sho...

America’s affordable housing crisis is well documented. We’re currently short millions of homes, and the number doesn’t seem to be going down.

The problem is more complicated, but more solvable, than it appears. Factory-built housing—such as manufactured and mobile homes—has helped fill the gap for decades, and the capacity to build substantially more already exists.

Now, new products are entering the market. Galiano Tiramani, co-founder and CEO of modular home manufacturer BOXABL, is spearheading the effort to produce their own model of affordable housing at scale.

But as you’re abo...

Real estate investors spend years mastering skills like analyzing deals, raising capital, and improving operations, but far less time thinking about one of the most important decisions they’ll ever make: the exit.

Mike Hart, chief financial officer here at Sunrise Capital Investors, believes you should start planning your exit roughly a year prior to the actual sale, as this affects when you’ll pay taxes, what you’ll pay, and depending on the strategy, if you’ll pay at all.

With over 30 years of commercial real estate experience, Mike has helped countless investors make smarter...

Many get into real estate with the goal of scaling a massive portfolio. Not enough stop to ask whether they should. The truth is that success doesn’t come from chasing every last opportunity. It’s about identifying where you have an edge, choosing your partners carefully, and having the discipline to walk away when a deal doesn’t quite fit.

John McNellis is the founder of McNellis Partners and author of the commercial real estate classic, Making It in Real Estate. Over the course of a 50-year career, he’s completed roughly 100 real estate deals—most of which h...

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 323-unit portfolio looked like a complicated deal with questionable management and an inflated asking price. Not to mention, most of...

Imagine owning a property with enormous upside, but one that’s operationally complex and requires hundreds of thousands or even millions in capital improvements. What do you do? Selling leaves value on the table. A joint venture dilutes control and introduces unnecessary risk. So what’s the alternative?

One of commercial real estate’s most underutilized capital structures: the ground lease.

Danielle Ash, partner and co-chair of the ground lease practice at Adler & Stachenfeld, has helped countless investors generate predictable cash flow, preserve long-term ownership, and even unlock trapped equity with this often-overlooked strategy.

She...

When investors hear the term USDA loan, they tend to picture small towns, farmland, and niche financing. In reality, they may be overlooking one of the best—and least understood—government-backed loan programs available for commercial real estate.

In many cases, the USDA loan is an even better option than both the SBA loan and conventional financing. To explain why, we’re joined by Jordan Blanchard, commercial lending expert and co-founder of X-Caliber Rural Capital. With more than 30 years of banking and lending experience, Jordan has built a career out of helping investors unlock borrowing opportunities—like USDA fin...

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 mortgage brokerage HB Capital, has a unique vantage point on this dynamic. Through thousands of relationships with operators and lenders nationwide, she sits at the intersection of capital markets and commercial real estate investing. Not to...

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 lower the barrier to entry and bring these opportunities down to the average person.

In 2022, that dream became a reality when he launched Mogul, a real estate investing platform that allows us...

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 sluggish rent growth.

In the industrial space, the opposite happened.

As new construction came to a screeching halt in many of Joel’s ma...

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 strategy, and deep tenant relationships have shaped his resilient approach to real estate investing.

Joel's early entrepreneurial start and entry into industrial real estate

The lessons learned from the 2008...

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 operator who’s growing steadily, tackling smaller multifamily deals, and having no troubl...

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 these anchor institutions to breathe new life into college towns throughout the U.S.

By creating strong ties with premier universities and form...

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 deals we’ve taken down at...

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 20% on their premium costs and sometimes even making them a profit on insuring their properties. 

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 internet stocks, Dwight acquired a 378-unit apartment community. He was stepping in...

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 experience as a commercial real estate architect, Lisa is asking the question most people aren’t...

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 investments.

Now, as the founder of Novo Capital Management...

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 study that proves if you put in the wo...

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 of the hardest markets in America—California. But that’s not all—sh...

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.

Lynn Jerath, founder of Citrine Investment Group, has a battle-tested background in REIT investing, hospitality, multifamil...

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 caused him to reconsider where he wanted to invest for the next 10, 20, or 30 years.

In this ep...

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 opportunities that once felt out of reach for everyday investors. At the same time, there’s been a growing shift toward debt investments, many of...

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 that delivers sizable returns to passive investors through value-add multifamily properties. Mark has overseen thousands of apartment units and...

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, with limited supply, and durable cash flow potential that institutional investors are finally starting to recogni...

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 years of commercial real estate investing experience, Brad has had to wear several hats. Today, he primarily focuses on curating portfolios of c...

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 every investor would gladly pull the trigger on. But most investors overlook the opportunity directly in front of them—parking lots.<...

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 strategies most operators overlook: in-house property management and public-private partnerships (P3s).

First, Kent...

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. This wasn’t by luck, but by design, and Andrew’s advice can help any investor, whether...

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 investing arsenal. If you think your property is too small...

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 sponsor-vetting checklist. 

With decades of experience i...

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 sentiment shift toward one forgotten asset class office space investing. Office investments are seeing supply get actively demolish...

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 five years plan, consult, construct, and let the 3rd-party self-storage management team take care of...