Real Estate Investing for Cash Flow with Kevin Bupp

Kevin Bupp
  • 4.8 (673)
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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

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

    5D AGO

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

    This could be one of the highest ROI strategies in real estate, yet most investors ignore it. Imagine getting hundreds of thousands of dollars in write-offs, saving tens of thousands in taxes, all while you own income-producing, equity-building real estate. Most investors think they know what we’re talking about in today’s show, but if they did, they’d be jumping at the chance to use it. It’s no secret—cost segregation studies can become one of the most profitable weapons in your real estate investing arsenal. If you think your property is too small, too old, or too cheap to use one, Kim Lochridge, Executive Vice President for Engineered Tax Services, plans to prove you wrong. Kim and her team conduct over 800 cost segregation studies a month on properties ranging from five-figure rentals to multimillion-dollar assets. She’s answering every question: What is a cost segregation study? How much does a cost segregation study cost? How much can you write off? Plus, why passive investors can unlock a treasure trove of paper losses, even if they’re still working a W-2 job. That’s not all. Kim shares the most tax-advantaged assets investors can’t ignore, and the audit red flags she learned from a nightmare encounter with the IRS.  This isn’t just about saving on taxes; this is about unlocking tens of thousands in tax savings that materially improve cash flow. Insights from today’s episode: Cost segregation studies explained: what they are, how much they cost, and who can use them The five most tax-advantaged assets with massive bonus depreciation potential  Audit red flags and an easy way to protect yourself from the IRS The “lazy 1031 exchange” that eliminates the tight timeline to find and buy a property  How passive investors can mitigate tens of thousands in taxes with cost segregation studies (you don’t need to be a real estate professional)  — Connect with Kim on LinkedIn Engineered Tax Services Real Estate Investing for Cash Flow 230 - Cost Segregation Explained – with Kimberly Lochridge Recommended Resources: Accredited Investors, you’re invited to Join the Cashflow 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

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

    FEB 2

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

    Everyone plans to “buy the dip” until it’s time to write the check. Multifamily opportunities are rising, and with properties 20%+ off the peak of pricing, investors are getting flooded with “deals.” But, like we learned over the past five years, the wrong sponsor (even with the right deal) can kill your returns and blow up the wealth you spent so long to build.  So, how do you spot the opportunities vs. the landmines in multifamily? We brought on fund of funds manager, Lon Welsh, to share his sponsor-vetting checklist.  With decades of experience in real estate investing, launching his capital fund in 2022 could have been disastrous (rising interest rates, rent growth freezes, expanding cap rates), but to this day, Lon has over a 90% success rate across funds within his own fund. This wasn’t done by guessing or gut-checks, but carefully choosing the right sponsor for the right deal. Today, Lon shares his own sponsor-vetting checklist, how he personally confirms a deal is worth getting into, the best multifamily markets in the country with easing supply, low regulation, and strong demand, and how to ensure a sponsor was intentional, not lucky, in achieving their past successes.  Plus, we even get Lon’s multifamily prediction for 2026-2027. Insights from today’s episode: How to vet a multifamily sponsor before putting a dollar into their deal Why a “fund of funds” could be the more diversified, safer bet than real estate syndications  What to look at to ensure a sponsor wasn’t just “lucky” during past deal cycles  The best places to invest in multifamily right now (2026) where supply is about to drop off How to feel confident buying during a dip when everyone else is too scared to act  Lon’s medical receivables play making passive income without a single property  — Connect with Lon on LinkedIn Ironton Capital Recommended Resources: Accredited Investors, you’re invited to Join the Cashflow 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.

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

    JAN 26

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

    This could be commercial real estate’s “buy of the decade,” according to a 35-year investing veteran. This asset class is seeing rock-bottom prices, shrinking supply, and acquisitions at a quarter of replacement cost. Everyone says this asset is dead, so why are expert investors, lenders, and brokers betting on it? Michael Bull, founder & CEO of Bull Realty, Inc., has personally overseen over $8 billion in commercial real estate transactions in his 35 years in the industry. He’s seeing sentiment shift toward one forgotten asset class office space investing. Office investments are seeing supply get actively demolished, but lending and buying are returning, and some cities are even seeing more office demand.  The media is saying it’s all doom and gloom, but on the ground, Michael is seeing something very different. Want to buy when the fear is still high, but prices are touching bedrock? Michael shares his underwriting playbook for finding valuable office investments, what savvy operators are doing with outdated office vintages (demolish, rebuild, or retrofit?), and the markets with the most opportunity for demand. Plus, the exact type of tenant that is giving those who invest in office space consistent revenue and unmatched peace of mind. Insights from today’s episode: Commercial real estate’s “buy of the decade” and why investors are jumping back in No new supply coming online? Why office building supply is shrinking, just as demand bounces back  Underwriting “guardrails” experts use to validate a valuable vs. dead office investment  First office investment? Where Michael says beginners should start looking for opportunities   Falling values = falling property taxes? An even bigger lever for cash flow  Retrofit, rehab, or convert? How to add value to old, outdated office vintages  — Connect with Michael on LinkedIn Buy or Sell with Bull Realty America’s Commercial Real Estate Show Podcast Recommended Resources: Accredited Investors, you’re invited to Join the Cashflow 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.

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

    JAN 19

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

    Just over five years ago, express car washes were peaking. Private equity was getting in, ready to buy up these cash-flowing projects at high prices. At this moment, Ben Salzberg and Bill Kanatas knew it was time to get out and pivot toward an even more durable asset. What did they turn to? Self-storage, and not your average mom-and-pop shop. Class-A, climate-controlled, multi-story facilities that self-storage REITs could easily come in and run. It’s a blueprint that has worked for them for five years plan, consult, construct, and let the 3rd-party self-storage management team take care of the rest. But there’s much more to this strategy than building a pretty box. On today’s show, Ben and Bill outline the exact blueprint they use to build REIT-ready self-storage facilities, how to work with big names (Public Storage, Extra Space, CubeSmart) before you lay a single brick, what to look for in a market before you decide to build, and why entitling land, turning dirt into dollars is more worth it than you think. Plus, Ben and Bill share the optimal storage facility size (and demand ratios) so you know what REITs and customers want. Insights from today’s episode: A REIT-ready self-storage development blueprint from 30-year development veterans The 3rd-party self-storage management that instantly plugs into your facility  Why Ben and Bill left cash-flowing car washes for class-A self-storage facilities  Signs a market is too saturated with self-storage (and what to look for instead) Getting the city on your side—how to create a win-win for local government, residents, and your investment  Entitling land—is it worth the effort to turn raw dirt into a buildable lot? — Connect with Ben on LinkedIn Connect with Bill on LinkedIn Work with Self Storage Developers  Email Self Storage Developers: info@self-storagedevelopers.com  Recommended Resources: Accredited Investors, you’re invited to Join the Cashflow 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/Podcas

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

    JAN 12

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

    Every multifamily operator wants to know how to increase NOI, but they’re not doing it the right way. Traditional renovations leading to rent increases have been harder to get right in the past few years. But what if there was a “hidden” source of not only higher revenue but also lower expenses—something 99% of operators are unaware of, that could increase NOI by tens of thousands per month. Today, Bill Douglas of OpticWise (https://www.opticwise.com/) and Marcy Sagel of MSA Interiors (https://msainteriors.com/), CRE technology and design experts, join us to talk about the NOI levers nobody is thinking of pulling. We’ll share the actual amenities and tactics you can use today in your building to attract higher-paying tenants and turn utility expenses into revenue, with game changing effects on your bottom line. Plus, what buy-and-hold vs. short term flip investors must include in their budget to get the maximum NOI possible.  One amenity our experts say is an actual waste of money…unless you hear how to monetize it properly.  Retrofitting an older vintage multifamily? Bill and Marcy share exactly how to track which design changes are working for your bottom line, how to go from antiquated to next-level tech, and the hidden value-add opportunities you can implement starting today. Plus, why your property management company could be stopping you from making tens of thousands more every month!  Insights from today’s episode: The “hidden” NOI opportunities that most multifamily operators completely miss  One amenity you can provide that could increase your revenue $80-$90 PER unit The design tweaks younger renters require that move the needle on NOI  An expert checklist on renovating and retrofitting 1980s vintage to today’s standards  Data you can start collecting now that shows precisely what tenants want/don’t  The best piece of advice for anyone building a new multifamily (could boost your NOI)  Connect with Bill on LinkedIn (https://www.linkedin.com/in/billdouglas/) OpticWise (https://www.opticwise.com/) Grab Bill’s Book, Peak Property Performance (https://www.peakpropertyperformance.com/) Listen to Bill’s Peak Property Performance Podcast (https://podcasts.apple.com/us/podcast/peak-property-performance/id1817250978) Connect with Marcy on LinkedIn (https://www.linkedin.com/in/marcysagel/) MSA Interiors (https://msainteriors.com/) Recommended Resources: Accredited Investors, you’re invited to Join the Cashflow 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/)! 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.

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

    JAN 5

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

    What does it take to go from growing up in a mobile home…to owning hundreds of mobile home lots across the country? Today’s guest, my business partner Brian Spear, is living proof that mindset and mission matter more than where you start. In this episode, Brian shares his remarkable journey into mobile home park investing, the lessons from the wealthy that helped him build long-term success, and how we joined forces to build Sunrise Capital Investors—with mobile home park investments totaling in the hundreds of millions. We go deep on what makes buying a mobile home park such a powerful wealth-building tool, the character traits that separate long-term winners from short-term speculators, and how we’ve used investing as a vehicle for something more than just financial gain. This isn’t just an investing episode—it’s a blueprint for building both cash flow and character. Insights from today’s episode: How Brian went from tenant to owner in the mobile home park space Lessons from the wealthy that can reshape how you approach investing Why "burning the boats" is essential if you want to succeed Why mobile home park investing remains a recession-resistant strategy The power of delayed gratification, frugality, and compounding wisdom What it means to pass down wisdom—not just wealth — Connect with Brian on LinkedIn Listen to The Sage Investor Podcast Recommended Resources: Accredited Investors, you’re invited to Join the Cashflow 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.

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

    12/29/2025

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

    More syndications are going sideways. Capital calls have become common. Tensions are rising between operators and investors…but not for all deals. If you had talked to today’s guest before forming your real estate syndication, there’s a good chance you’d already have a battle plan for every potential challenge. Thankfully, today, CRE’s go-to legal advisor is sharing his take for free. Richard Crouch has worked on eight figure commercial real estate deals for over two decades, helping advise on disputes, defaults, and structuring. He’s the one who sets up your failsafes before a deal goes sideways and advises you on the right way to resolve it once the damage has been done. Today, we’re getting into the nitty-gritty that not only sponsors but also passive investors need to know. We’ll talk about the “gotcha” clauses lenders can use to extract fees from you or worse…take your entire property, the right way to handle a capital call so your exit strategy doesn’t fall apart, and what to do in the unfortunate event that a guarantor passes away mid-deal.  Insights from today’s episode: Your lender is not your friend: the “gotchas” put in place that you must navigate around  How to handle capital calls so your investors don’t feel neglected and unsettled  One thing you need to include in every single operating agreement you sign  A crucial event that can “trigger” if a guarantor passes away during a deal cycle  Opportunity for buyers: Is now the time to invest in distressed debt amid inexperienced syndicators' struggles — Connect with Richard on LinkedIn Richard’s Email: richard.crouch@woodsrogers.com  Richard’s Phone Number: 757-353-0969 Recommended Resources: Accredited Investors, you’re invited to Join the Cashflow 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.

    29 min
  8. How We Bought $80M of Real Estate This Year + Huge Announcement

    12/22/2025

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

    2025 is about to be in the books, and for many real estate investors, it was a challenging year. But at Sunrise Capital, it’s been a year of massive growth, disciplined pivots, and, for me, purpose: my wife and two sons.  We’ve acquired $80,000,000 in new assets this year—irreplaceable real estate that we couldn’t pass up. We’ve had to step away from other deals when the numbers didn’t pencil, and in the end, we’re monumentally proud of what we’ve accomplished. So what’s next? I have a big announcement at the end of this episode—and this is the first time I’m going public with it. My life, and the lives of my family, are about to change as we do something I’ve been dreaming about for over a decade. This is what it was all for. But before that, I’ll share the lessons we learned in 2025 that shaped our business and buying decisions, why capital raising wasn’t as hard as many sponsors think it is (if you operate the way we do), and why we didn’t have to change our underwriting during some of the most challenging years of investing in decades. I’m sharing the wins and losses, both personal and professional, on today’s show. Thank you for a wonderful 2025. 2026 is going to be a little…different.  Insights from today’s episode: A huge announcement that has been over a decade in the making  How we acquired $80M in irreplaceable assets and raised the money for it in 2025 The discipline you need to walk away from a deal that goes sideways (you won’t regret it) How to raise capital the right way, and why you should stop selling yourself (and your deals) so hard The commitments I’m making in 2026 (you can keep me accountable!)  Recommended Resources: Accredited Investors, you’re invited to Join the Cashflow 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.

    25 min
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4.8
out of 5
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About

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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