Real Estate Investing for Cash Flow with Kevin Bupp

Episodios

• 
  He Walked Away Mid-Deal. It Cost Him $100,000 (But Saved His Investors) 14.09.2026 51m

  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 rationalizing what had become a “bad” deal, August and his team made the difficult decision to change course and abandon the deal. Had they not, the fund would likely have been wiped out. Instead, CPI Capital has grown to well over $225 million in value-add multifamily and built-to-rent, single-family assets under management in the last several years.   In today’s conversation, August shares how these early lessons shaped the way they approach risk and opened the door for even greater investing opportunities. Insights from today’s episode: When to walk away from a deal when the numbers no longer work Why August and his team opted for a co-GP approach on their first few deals How to stay competitive in large markets as a middle-market operator How to properly structure a cross-border investment The main differences between built-to-rent tenants and other renters — CPI Capital   Connect with August on LinkedIn Recommended Resources: If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, click here for opportunities to invest in real estate projects alongside Kevin and his team.  Accredited Investors, you’re invited to Join the Cash Flow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club! Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com.  Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast. Chapters:  00:00 Intro 00:47 Pivoting to US Real Estate 10:20 Cross-Border Complexity 15:05 The Co-GP Approach 19:37 Finding Opportunity in Big Markets 25:25 How to Stay Competitive 28:37 The Build-to-Rent Model 34:17 Walking Away (And Losing $100K) 41:41 Advice for New Investors 46:57 What Has Changed? Disclaimer: This podcast is for educational purposes only and does not constitute financial, tax, or legal advice. Consult with a qualified professional before making any investment decisions.
• 
  99% Passed on These Commercial Properties. They Made Him a Fortune. 07.09.2026 45m

  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 caused Bill to rethink his entire philosophy about business and wealth. Having arrived at his own definition of “enough” long ago, Bill has since turned his attention to a much bigger purpose: the Cummings Foundation, which has awarded over $650 million in grants to nonprofits throughout the suburbs of Boston and beyond. But to understand how Bill built an empire, we have to go back to the beginning. In this episode, he shares the early successes, failures, and the simple conversations with his father that influenced his views on price, value, opportunity, and what actually makes a great investment. Insights from today’s episode: Why Bill repeatedly buys properties most developers pass up The $500,000 commercial property no one wanted (that made a fortune) The key to maintaining high occupancy in commercial real estate The one type of commercial building Bill refuses to buy How to define “enough,” and what to do once you reach it — Cummings Properties Cummings Foundation Starting Small and Making It Big Recommended Resources: If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, click here for opportunities to invest in real estate projects alongside Kevin and his team.  Accredited Investors, you’re invited to Join the Cash Flow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club! Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com.  Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast. Disclaimer: This podcast is for educational purposes only and does not constitute financial, tax, or legal advice. Consult with a qualified professional before making any investment decisions. 00:00 Lessons from 50+ Years in Real Estate 05:43 Local, Buy-and-Hold Investing 12:01 Building Strong Culture 16:18 The Property "No One Wanted" 25:59 Bill's Recent Deal 31:14 How to Improve Occupancy 33:13 Property Red Flags 36:20 What Is "Enough"? 40:11 The Cummings Foundation 43:24 Connect with Bill!
• 
  He Tripled His Cash Flow by Doing What Most Buy-and-Hold Investors Won’t | Ep. 1003 31.08.2026 56m

  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 whether an investment is still the best use of their capital, time, and energy.   Chris learned this lesson when he decided to finally cut ties with rental properties that no longer aligned with his long-term goals. After selling multiple rental properties and moving much of his capital into more hassle-free, passive real estate investments, he had just one regret: not doing it sooner. Chris shares exactly what prompted the pivot toward passive investments, what he looks for when evaluating sponsors, and how to curate an investment portfolio that helps you build wealth without losing sight of your end goal. Insights from today’s episode: How Chris tripled his cash flow by moving from “headache” rentals into passive investments How to offset your capital gains taxes with the “lazy” 1031 exchange Why “passive” investing isn’t nearly as hands-off as many assume The biggest red flags to avoid when vetting a sponsor A cautionary tale for investors banking on future rent growth Real estate’s biggest investing advantages over stocks and bonds — Connect with Chris on LinkedIn Property Llama PassivePockets Recommended Resources: If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, click here for opportunities to invest in real estate projects alongside Kevin and his team.  Accredited Investors, you’re invited to Join the Cash Flow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club! Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com.  Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast. Disclaimer: This podcast is for educational purposes only and does not constitute financial, tax, or legal advice. Consult with a qualified professional before making any investment decisions.
• 
  How to Earn a 13%-18% Average Annual Return in 2026 (Tax Lien Investing 101) | Ep. 1002 24.08.2026 51m

  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 shortcut to acquiring cheap properties. In fact, only 1% of these properties ever get foreclosed on. Rather, tax lien investing is a yield play. Unfortunately, due to the complexity surrounding these investments, institutional investors with access to large amounts of capital have long had a stranglehold on this industry. Stephen is on a mission to change that. Through his tech startup, JurisDeed, he’s breaking down barriers and finally bringing these strong returns down to the level of the “small” investor. Today, he shares exactly how he and his team are simplifying the entire process—from acquisition to liquidity. Insights from today’s episode: How to make double-digit returns in 2026 by investing in tax liens Tax lien investing explained and how the auction process works The two phases of due diligence for every tax lien deal Why institutional investors have long dominated the tax lien marketplace How Stephen is bringing new investing opportunities down to “small” investors — Connect with Stephen on LinkedIn JurisDeed Recommended Resources: If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, click here for opportunities to invest in real estate projects alongside Kevin and his team.  Accredited Investors, you’re invited to Join the Cash Flow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club! Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com.  Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast. Disclaimer: This podcast is for educational purposes only and does not constitute financial, tax, or legal advice. Consult with a qualified professional before making any investment decisions.
• 
  The State of Affordable Housing in 2026 w/ BOXABL CEO Galiano Tiramani | Ep. 1001 17.08.2026 22m

  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 about to hear, the greatest obstacle isn’t manufacturing, construction, supply, or even shipping. The real constraint is regulatory. Zoning restrictions, entitlement delays, and density limitations continue to determine where—and how—homes can be built. Unless these outdated policies evolve, we’ll be discussing the same housing shortage five, 10, or even 20 years from now. The technology exists, the capacity exists, and the demand is undeniable. The future of affordable housing is here; now we need to make room for it. Insights from today’s episode: The state of affordable housing in 2026 (and why it’s still an issue) Why innovation alone won’t solve the affordable housing crisis The model BOXABL is using to bring mass-produced modular homes to the market The different types of factory-built housing solutions (and how they work) How regulatory constraints have created an affordable housing bottleneck — Connect with Galiano on LinkedIn   BOXABL Recommended Resources: If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, click here for opportunities to invest in real estate projects alongside Kevin and his team.  Accredited Investors, you’re invited to Join the Cash Flow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club! Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com.  Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast. Disclaimer: This podcast is for educational purposes only and does not constitute financial, tax, or legal advice. Consult with a qualified professional before making any investment decisions.
• 
  The Keys to a Tax-Efficient Real Estate Exit (1031 Exchanges, DSTs, & More) | Ep. 1000 10.08.2026 40m

  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 capital allocation and tax-efficient investing decisions. In this conversation, he unpacks some of the best real estate tax strategies used to defer capital gains tax and depreciation recapture, starting with the well-known 1031 exchange. He also breaks down some lesser-known alternatives, including Delaware Statutory Trusts (DSTs), and explains how they can help investors transition from active property management to passive ownership while continuing to defer taxes. Whether you’re looking to peel back from being a hands-on operator or preserve your wealth, this discussion will help you think more strategically about your next sale. Insights from today’s episode: The best strategies for deferring capital gains taxes and depreciation recapture The number one mistake real estate investors make when planning their exit strategy How to pivot from active owner to passive investor with a Delaware Statutory Trust (DST) Key rules and deadlines to be aware of before doing a 1031 exchange How to perform due diligence on a DST trustee before committing capital — Connect with Mike on LinkedIn Recommended Resources: If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, click here for opportunities to invest in real estate projects alongside Kevin and his team.  Accredited Investors, you’re invited to Join the Cash Flow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club! Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com.  Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast. Disclaimer: This podcast is for educational purposes only and does not constitute financial, tax, or legal advice. Consult with a qualified professional before making any investment decisions.
• 
  50 Years and 100+ Real Estate Development Deals: What I’ve Learned | Ep 999 03.08.2026 50m

  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 have been ground-up commercial development projects. Through thick and thin, John has stuck with retail real estate—even while others were predicting its downfall—and the asset class has made him very wealthy. But stay in real estate for long enough, and you’re bound to lose money. John opens up about the disastrous deal that nearly wiped him out, the three critical mistakes that caused it, and why he no longer works with big financial partners on his development deals. He also discusses the biggest mistakes new real estate developers make early in their careers and the million-dollar question every investor is trying to answer: what is “enough”? Insights from today’s episode: How John scaled a large commercial real estate portfolio through strategic partnerships Crucial lessons learned across a 50-year real estate development career When to stop accumulating assets and start pruning your portfolio How retail real estate has evolved over the last few decades What to know before structuring an investing partnership The three most common mistakes made on commercial development deals — Making It in Real Estate Connect with John on LinkedIn McNellis Partners Recommended Resources: If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, click here for opportunities to invest in real estate projects alongside Kevin and his team.  Accredited Investors, you’re invited to Join the Cash Flow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club! Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com.  Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast. Disclaimer: This podcast is for educational purposes only and does not constitute financial, tax, or legal advice. Consult with a qualified professional before making any investment decisions.
• 
  Real Deals: 15% Above Projections on a “Risky” Deal Everyone Else Passed Up 27.07.2026 23m

  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 these sites were park-owned homes, something that would usually fall outside our buy box. But rather than writing the property off, we identified its biggest “weakness” as a potential value-add opportunity. When other investors passed on this $20,000,000 deal due to its perceived risk, we trusted our numbers, backed in our leadership, and got to work. Nearly three years later, these two communities have already become some of our portfolio’s strongest performers, with NOI, occupancy, collections, and rents all outperforming our initial projections. But we didn’t get lucky. I’m sharing exactly how our team pulled this off, the biggest hurdles we had to overcome along the way, and what far too many operators get wrong: that strategy without execution is just theory. Insights from today’s episode: Case study: our $20 million manufactured housing deal in Columbus, Ohio Why these communities are performing 15% above projections The one thing you can’t fix about a property after purchasing it How to mitigate perceived risk with “conservative” deal analysis Turning an asset’s “weakness” into its biggest value-add opportunity — Ridgebrook Hills MHP Case Study Real Deals: The Biggest Mobile Home Community We’ve Ever Bought | Ep. 990
• 
  How to Lock in 99 Years of Cash Flow (Today) with Commercial Ground Leases | Ep. 997 20.07.2026 42m

  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 unpacks the three main “buckets” of ground leases, along with the sale-leaseback option that allows owner-operators to create liquidity for other projects. Danielle also shares a real-world case study involving a New York City property with massive potential and a $200 million renovation, managed and paid for by the lessee.  Whether the goal is to free up capital for future acquisitions or create a long-term passive income stream while benefitting from capital improvements, the ground lease is a powerful tool worth exploring. Insights from today’s episode: How to create long-term cash flow with commercial ground leases A real case study of a New York City ground lease deal involving a $200 million renovation (paid by the lessee!) The biggest risks to consider before entering into a ground lease agreement Why a ground lease is often a win-win for both owner and operator What lenders look for when underwriting ground lease tenants How owner-operators can create liquidity through sale-leasebacks
• 
  How to Fund Your Next Commercial Real Estate Deal with USDA Financing | Ep. 996 13.07.2026 37m

  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 financing—many don’t realize exist. Jordan unpacks the loan’s biggest advantages and trade-offs while dispelling the biggest misconceptions surrounding it. He also shares exactly what investors need to know before applying, as well as how to layer other financing options and tax credits into an efficient capital stack. There’s no sugarcoating it: USDA loans can be difficult to qualify for. But for investors needing large amounts of capital, flexible terms, and a lower-money-down alternative to conventional financing, the payoff is well worth it. Insights from today’s episode: USDA loans—how they work, who they’re for, and common misconceptions How to quickly determine if you’re eligible for a USDA loan USDA versus SBA versus conventional financing (pros and cons) The ideal capital “stack” for funding commercial real estate deals Inside the $185 million deal Jordan and his team recently closed The five most common reasons why operators default on commercial loans 00:00 Intro 03:05 USDA Lending 101 08:12 2 Common Misconceptions 11:52 Longer, More Flexible Terms 14:36 Creating Your Capital "Stack" 21:20 Who Is USDA-Eligible? 22:55 Biggest Investor Mistakes 32:08 5 Rapid-Fire Questions! 35:42 Connect with Jordan! — Connect with Jordan on LinkedIn   X-Caliber Rural Capital Email Jordan at [email protected] Recommended Resources: If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, click here for opportunities to invest in real estate projects alongside Kevin and his team.  Accredited Investors, you’re invited to Join the Cash Flow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club! Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com.  Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast. Disclaimer: This podcast is for educational purposes only and does not constitute financial, tax, or legal advice. Consult with a qualified professional before making any investment decisions.
• 
  She Oversees $150M Acquisitions: Here’s What “Smart” Operators Are Doing Today w/Hannah Hammond 06.07.2026 50m

  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 mention, Hannah has scaled her own multimillion-dollar residential real estate portfolio. But the principles that guide her investment decisions today were shaped by more than market cycles. Raised in a family that struggled financially, Hannah believed money was the key to peace, happiness, and opportunity. This was only partially true. What she discovered after quitting corporate America for entrepreneurship, starting multiple businesses, and achieving financial freedom was that real “wealth” had much more to do with a life rooted in flow, not force. In today’s conversation, she shares about the painful experiences that shaped her, lessons from failed partnerships, and why the “disciplined” investors from a few years ago are the ones capitalizing on opportunities emerging from market distress. Insights from today’s episode: Hannah’s personal journey from financial hardship to financial freedom Why Hannah quit her comfortable engineering career to go all-in on real estate Lessons learned from failed partnerships and risky private lending experiences How Hannah’s engineering background has influenced her underwriting and risk tolerance The three fatal mistakes that cause operators to go underwater on assets Why true wealth stems from being fully aligned with your values and purpose—not money How to craft a daily routine that allows you to live through flow, not force —   Connect with Hannah on Instagram   HB Capital Recommended Resources: If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, click here for opportunities to invest in real estate projects alongside Kevin and his team.  Accredited Investors, you’re invited to Join the Cash Flow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club! Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com.  Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast. 00:00 From Scarcity to Abundance 04:09 Quitting Corporate at 21 06:15 Where Operators Are Winning 12:17 Inside the Phoenix Market 18:56 Taking "Calculated" Risks 21:59 Learning from Loss & Failure 25:44 Launching HB Capital 30:08 Attracting Top Talent 34:58 What Is Real "Wealth"? 41:18 Hannah's Daily Routine 45:43 The Next 5 Years 49:36 Connect with Hannah! Disclaimer: This podcast is for educational purposes only and does not constitute financial, tax, or legal advice. Consult with a qualified professional before making any investment decisions.
• 
  He Left Goldman Sachs to Bring Residential Real Estate to “Normal” Investors | Ep. 994 29.06.2026 36m

  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 users to buy fractional shares of residential properties in a matter of clicks. Think Airbnbs in vacation markets, quadplexes with long-term tenants, and even single-family homes that are rented by the room. With new offerings weekly, investment minimums of just $250, and all the benefits of direct ownership—but without any of the normal landlord responsibilities—everyday people can now buy affordable shares of rental properties in top markets across the U.S. Whether you’re a seasoned investor or just beginning your journey, this conversation will challenge what you thought was possible with real estate investing and the resources required to build real, long-term wealth. Insights from today’s episode: Why Alex left Goldman Sachs to start a fractional real estate investing platform How to reap all the benefits of rental property ownership without being a landlord The Mogul “model” that delivers higher annual returns than many REITs Residential real estate opportunities with $250 investment minimums The high-ROI real estate markets Alex and his team are targeting across the Sun Belt — Connect with Alex on LinkedIn Mogul Recommended Resources: If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, click here for opportunities to invest in real estate projects alongside Kevin and his team.  Accredited Investors, you’re invited to Join the Cash Flow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club! Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com.  Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast. 00:00 Intro 01:21 What Is the Mogul "Model"? 06:22 Managing the Properties 09:06 High-ROI Sun Belt Markets 16:03 Mogul Property Performance 21:50 Advantages Over REITs 26:28 Weathering the Airbnb "Storm" 34:03 Investing with $250! 35:26 Connect with Alex!
• 
  Industrial Real Estate Did the Last Thing He Expected (And It Made Him Wealthy) | Ep. 993 22.06.2026 57m

  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 markets, supply constraints drove rents higher, particularly for many of his class-B investments. But that’s just the most recent cycle. Joel’s thesis has been tested repeatedly throughout his 40-plus-year career, and he’s survived it all—not because he’s immune to failure, but because he stuck to fundamentals while the syndicators around him played with fire and got burned. His no-debt model has made raising capital significantly more challenging, but it’s also helped him weather storms that have wiped out riskier investments. Joel doesn’t use unrealistic pro forma to gain an edge. Instead, he focuses on mitigating risk, playing the long game, and hunting down off-market opportunities most operators don’t have the patience to pursue. It’s helped him win strong deals—and it could help you do the same. Insights from today’s episode: Why industrial real estate has outperformed other asset classes in many markets The three biggest red flags Joel avoids on industrial real estate deals The economic factors that caused industrial rents to double in the last four years Creating an edge in your market with off-market investing opportunities Why location and size matter more than the purchase price of industrial buildings The conservative approach to leverage that gives you more staying power — Hear Our Last Interview with Joel Connect with Joel on LinkedIn   Brit Properties Recommended Resources: If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, go to InvestWithKB.com for opportunities to invest in real estate projects alongside Kevin and his team.  Accredited Investors, you’re invited to Join the Cash Flow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club! Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com.  Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast. 00:00 Intro 02:00 What Happened to Industrial? 10:20 Creating an Edge 14:37 Joel's "Problem" Property 15:29 The 4 D's 27:46 Managing LP Expectations 35:39 The No-Debt Investing Model 50:48 Biggest Deal "Killers" 54:58 Connect with Joel!
• 
  Pioneering a Prudent Path in Industrial Real Estate | [Replay Ep. 686 ] 22.06.2026 42m

  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. Main topics - Key insights: Joel's early entrepreneurial start and entry into industrial real estate The lessons learned from the 2008 recession and their impact on his investment philosophy The shift from leveraging assets to pursuing low or no debt deals for stability How to identify and source industrial properties with strong tenant stickiness Strategies for deal structuring, including sale-leasebacks and niche tenant focus The importance of location, layout, and deal assumptions in industrial real estate Current market conditions and outlook for distressed assets and overbuilding risks Joel’s vision for the next three to five years, emphasizing stability and long-term value Hear Our Last Interview with Joel Connect with Joel on LinkedIn (https://www.linkedin.com/in/joel-friedland) Brit Properties (https://www.britproperties.com/) Recommended Resources: If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, go to InvestWithKB.com (http://investwithkb.com/?utm_source=podcast&utm_medium=shownotes&utm_campaign=rei4cf&utm_content=ep993) for opportunities to invest in real estate projects alongside Kevin and his team.  Accredited Investors, you’re invited to Join the Cash Flow Investor Club (https://kevinbupp.com/join/) to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club (https://kevinbupp.com/join/)! Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com.  Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast. 00:00 - Introduction to Joel Friedland and his investment philosophy 00:58 - Joel’s entrepreneurial beginnings and early real estate experience 01:44 - Lessons from the 1981 leasing market and mentorship influence 04:16 - Transition from brokering to property ownership and syndication 05:55 - Unpacking Joel's first industrial deal and key learnings 08:07 - The importance of property geometry and tenant needs in industrial 09:34 - Structuring early deals: legal and investor considerations 11:05 - Managing vacancy and lease strategy to attract user buyers 12:48 - Why the property was vacant and how tenants are typically found 14:19 - Impact of the 2008 recession and Joel’s personal and business recovery 16:38 - The shift to no-debt or low-leverage investing post-2008 17:35 - How Joel evaluates risk and manages investor expectations 20:06 - Market evolution and current overbuilding concerns 22:24 - Stress cracks in the real estate market and risk mitigation 24:39 - Market segments Joel is focusing on for stability 26:21 - Tenant-centric strategy and exit paths for industrial buildings 27:46 - Sale-leaseback opportunities and niche tenant strategies 30:22 - The ideal size and price points for industrial properties today 32:23 - Market catalysts that could challenge the industrial sector 34:58 - Overbuilt assets and overbuilding risks in large distribution centers 37:08 - Joel’s business outlook for the next three to five years 39:16 - Approach to deal sourcing and maintaining a conservative portfolio 41:53 - The importance of location, fundamental quality, and timing in industrial investing 42:22 - How to connect with Joel and stay updated on his ventures
• 
  What $100M Institutional Investors Look for Before Cutting the Check | Ep. 992 15.06.2026 52m

  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 trouble sourcing capital from dozens and sometimes hundreds of limited partners (LPs), perhaps not. But for the investor who has the means, it can immediately level up their business. As a liquidity provider for real estate sponsors, John is helping unlock some of these institutional-level opportunities. He shares how to make the jump from retail capital, how to underwrite passive and active investing opportunities properly, and what LPs must do to avoid getting burned by bad operators in 2026 and beyond. Insights from today’s episode: The infrastructure operators must build out before delving into institutional capital Why institutional capital isn’t automatically a better option than retail capital John’s two biggest lessons learned across a multi-decade career in real estate Why the quality of the sponsor matters more than the quality of the deal itself What passive investors must do to avoid getting burned by bad sponsors — Connect with John on LinkedIn   Peak 15 Capital Recommended Resources: If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, click here for opportunities to invest in real estate projects alongside Kevin and his team.  Accredited Investors, you’re invited to Join the Cash Flow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club! Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com.  Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast. 00:00 Intro 01:47 Is Institutional Capital Better? 09:57 “Upgrading” Your Business 16:44 Preparing for Institutional Capital 24:09 Recent Syndication Challenges 35:26 What Is Peak 15 Capital? 45:27 How to (Properly) Vet Sponsors
• 
  Top U.S. Universities Have a $1T Real Estate “Problem” (And He’s Solving It) 09.06.2026 35m

  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 forming strategic partnerships to access resources beyond just capital, Josh and his team have been able to bring economic stability to several disjointed communities. This level of specialization has allowed him to stand out at a time when other investors are swimming upstream against cutthroat competition and deteriorating margins. Josh’s message isn’t for more investors to try their hand at complex urban redevelopment deals. Rather, it’s that there are just two ways to create an edge in today’s market: become the next Blackstone, or niche down and dig deep. Insights from today’s episode: Josh’s journey into university-aligned real estate redevelopment Solving the $1 trillion problem that universities are facing over the next decade The two ways real estate operators can create an edge in today’s market Partnering with anchor institutions to revitalize “disjointed” communities Leveraging tax credits and government programs to offset development costs — Connect with Josh on LinkedIn   Ancora Recommended Resources: If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, click here for opportunities to invest in real estate projects alongside Kevin and his team.  Accredited Investors, you’re invited to Join the Cash Flow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club! Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com.  Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast. 00:00 Intro 01:12 Strategic University Partnerships 05:31 Josh's "Lightbulb" Moment 09:43 The South Bend Project 13:22 The $1T Development "Gap" 19:04 Identifying Top Opportunities 23:40 Structuring the Capital Stack 30:04 Niching Down in Real Estate 34:18 Connect with Josh!
• 
  Real Deals: The Biggest Mobile Home Community We’ve Ever Bought 01.06.2026 36m

  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 Sunrise Capital Investors, giving you an under-the-hood look at what went wrong, what went right, the real returns, and the money we spent.  This time, we’re in Fort Wayne, Indiana, taking a look at Ridgebrook Hills mobile home park, a community of over 700 lots, hundreds of residents, and huge infrastructure. What was supposed to be a homerun from the start turned into a steady stream of challenges for multiple years, but ended up being a rock-solid property we’re proud to own with huge upside.  I’m sharing all the challenges, budgets, and real return numbers in this episode so you can dodge some of the headwinds we hit along the journey.  Insights from today’s episode: How we landed a massive mobile home park by being disciplined when others were on buying sprees The real NOI numbers from this hugely improved mobile home park investment  The upside and value-add potential you can unlock with mismanaged mobile home parks  The staffing disaster that almost brought this deal to a halt (on day three!) An expense many investors overlook (we did!) that can cost you six-figures per year  The one thing that saved this deal (every investor or investment team needs this) — Check Out our Free Guide on Investing in Mobile Home Parks! Full Ridgebrook Hills MHP Case Study  Real Deals: A $10M Win by Taking on This “Complex” Parking Garage Deal | Ep. 985 Recommended Resources: Accredited Investors, you’re invited to Join the Cash Flow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club! If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, go to InvestWithKB.com for opportunities to invest in real estate projects alongside Kevin and his team.  Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com.  Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast.
• 
  The “Captive Insurance” for Landlords That Pays You to Protect Your Property 25.05.2026 32m

  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.  Nicolas Lares, CEO of Insur3Tech, worked as an insurance agent for years before ever hearing of "captive insurance” or “risk pooling.” When the small businesses he was tasked with insuring were being priced out so badly they could barely operate, he began building alternative structures, all federally backstopped, but without the middlemen.  Now, Nicolas’s clients are profiting from their insurance investment, getting premiums on average 20% lower, and getting claims paid out in a matter of days, not weeks.  How would your NOI improve if one of your greatest costs became a profit driver? Insights from today’s episode: The “risk pooling” insurance model that drops your insurance cost significantly  How to get paid to pay your premium (the insurance company actually pays Nicolas’s clients) Who can (and should) opt for "captive insurance” instead of the traditional route   The real reason why your landlord insurance premium is so high (it’s making insurance companies billions) How do these alternative providers make money without baking in a profit margin?  — Connect with Nicolas on LinkedIn Insur3Tech Recommended Resources: Accredited Investors, you’re invited to Join the Cash Flow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club! If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, go to InvestWithKB.com for opportunities to invest in real estate projects alongside Kevin and his team.  Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com.  Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast. 00:00 Insurance Is Broken in 2026 03:40 They're Making Billions off of Us 06:19 Cutting Out the Middlemen 11:58 The Insurance "Pool" Structure 16:23 Getting Paid to Insure Your Property 19:33 Who Can (and Should) Do This? 26:28 How Do THESE Providers Make Money? 31:15 Work with Nicolas!
• 
  Don’t Get Wiped Out: The Multifamily Investing Strategy That Beat 3 Downturns | Ep. 988 18.05.2026 38m

  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 into a struggling asset that demanded sizable improvements and millions in repairs, but this experience provided a crash course in operations, value-add investing, and asset management. Dwight says to become an old, rich investor, you’ve got to 1. get old and 2. not get wiped out along the way. So, he focuses on “asymmetric” investing opportunities that have capped downside but plenty of upside for good operators. Then, he further de-risks these assets by insourcing the things most operators would outsource.   In today’s conversation, we discuss all of this—the power of vertical integration, protecting assets and capital through downturns, and why long-term, buy-and-hold investing remains the surest path to generational wealth. Insights from today’s episode: - How Dwight protects his assets and capital with “anti-wipeout” investing - The keys to building a business that can survive any “Black Swan” event - Acquiring and managing a 378-unit apartment community at 25 years old - How to dramatically improve revenue with vertical integration - Why supply constraint, not job growth, is the surprising main driver of multifamily success — Connect with Dwight on LinkedIn   Bonaventure   Internet Subway   Vest Residential Recommended Resources: - Accredited Investors, you’re invited to Join the Cash Flow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club! - If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, go to InvestWithKB.com for opportunities to invest in real estate projects alongside Kevin and his team.  - Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com.  Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast. 00:00 Intro 00:45 Buying 370+ Units at 25 07:09 Surviving (& Winning) in 2008 11:17 Don't Get Wiped Out! 18:12 Buy-and-Hold (Forever!) 23:20 Vertical Integration 101 32:40 What's Next for Dwight? 37:27 Connect with Dwight!
• 
  Private Air Travel Is Coming: But the “Smart” Investing Play Is on the Ground | Ep. 987 11.05.2026 38m

  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 thinking of just yet: where will these aircraft actually land? As an early adopter, Lisa’s company is currently in a race to develop over 2,000 vertiport sites over the next five years. With little more than angel investments and bootstrapping, her team has already secured two-year land lease options throughout many rural communities where these amenities are likely to appear. In today’s conversation, Lisa shares the strategy that has helped her stay fluid without major capital raises, her long-term vision for building out a coast-to-coast vertiport network, and the revenue-share model that gives landowners an almost irresistible investing opportunity. Insights from today’s episode: Lisa’s five-year plan for developing a 2,000-site vertiport network How early adopters of advanced air mobility stand to profit in the years ahead Why private aviation is poised to become the new frontier of transportation The revenue-share model that gives rural landowners unique investing opportunities Creating multiple revenue streams with low-cost, low-maintenance landing sites — Connect with Lisa on LinkedIn   Landings Recommended Resources: Accredited Investors, you’re invited to Join the Cash Flow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club! If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, go to InvestWithKB.com for opportunities to invest in real estate projects alongside Kevin and his team.  Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com.  Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast. 00:00 The Spark for Landings 00:50 Intro 02:23 Why Private Aviation? 07:36 eVTOL Is Already Here 12:21 "Viable" Vertiport Sites 19:15 Costs & Revenue Share 25:19 How Does It Make Money? 27:09 Lisa's 5-Year Plan 30:58 Funding Vertiport Development 33:54 Connect with Lisa!