Real Estate Investing for Cash Flow with Kevin Bupp

Kevin Bupp
  • 4.8 (675)
  • Investing
  • Updated Weekly

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

  1. 20h ago

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

    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.

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

  2. Sep 7

    99% Passed on These Commercial Properties. They Made Him a Fortune.

    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!

    99% Passed on These Commercial Properties. They Made Him a Fortune.

  3. Aug 31

    He Tripled His Cash Flow by Doing What Most Buy-and-Hold Investors Won’t | Ep. 1003

    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.

    He Tripled His Cash Flow by Doing What Most Buy-and-Hold Investors Won’t | Ep. 1003

  4. Aug 24

    How to Earn a 13%-18% Average Annual Return in 2026 (Tax Lien Investing 101) | Ep. 1002

    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.

    How to Earn a 13%-18% Average Annual Return in 2026 (Tax Lien Investing 101) | Ep. 1002

  5. Aug 17

    The State of Affordable Housing in 2026 w/ BOXABL CEO Galiano Tiramani | Ep. 1001

    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 State of Affordable Housing in 2026 w/ BOXABL CEO Galiano Tiramani | Ep. 1001

  6. Aug 10

    The Keys to a Tax-Efficient Real Estate Exit (1031 Exchanges, DSTs, & More) | Ep. 1000

    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.

    The Keys to a Tax-Efficient Real Estate Exit (1031 Exchanges, DSTs, & More) | Ep. 1000

  7. Aug 3

    50 Years and 100+ Real Estate Development Deals: What I’ve Learned | Ep 999

    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.

    50 Years and 100+ Real Estate Development Deals: What I’ve Learned | Ep 999

  8. Jul 27

    Real Deals: 15% Above Projections on a “Risky” Deal Everyone Else Passed Up

    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

    Real Deals: 15% Above Projections on a “Risky” Deal Everyone Else Passed Up
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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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