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Real Estate Investing for Cash Flow with Kevin Bupp: Daily Summaries Delivered
by Kevin Bupp
There are a lot of real游戏副本 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 gener游戏副本ional 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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- 4 days ago36 min
Real Deals: The Biggest Mobile Home Community We’ve Ever Bought
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.
- 1 weeks ago32 min
The “Captive Insurance” for Landlords That Pays You to Protect Your Property
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!
- 2 weeks ago38 min
Don’t Get Wiped Out: The Multifamily Investing Strategy That Beat 3 Downturns | Ep. 988
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!
- 3 weeks ago38 min
Private Air Travel Is Coming: But the “Smart” Investing Play Is on the Ground | Ep. 987
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!
- May 4, 202641 min
From Zero to 1,200+ Multifamily Units in 7 Years (Replacing His W2 Income) | Ep. 986
Many investors talk about financial freedom, but few ever scale to the point where they can leave their W-2 jobs and live off the cash flow from their real estate investments. Jason Kenney did it. Completely burned out after two decades of climbing the corporate ladder, Jason and his wife started allocating their W-2 income to real estate assets with the goal of buying back their time. Within only a few years, Jason was able to quit his W-2 job and replace his income with cash-flowing investments. Now, as the founder of Novo Capital Management, Jason focuses exclusively on multifamily apartments, with a 1,200-unit portfolio spanning several markets. Having been on both sides of syndications, Jason offers a rare, dual perspective on operations and the process of vetting sponsors. Using his “SMART” framework, investors can do their own due diligence on general partners, syndication deals, and even active investments. In this conversation, Jason shares about some of his recent acquisitions, candid lessons from deals that didn’t pencil, and what investors need to do to truly stand out in today’s high-interest-rate environment. Insights from today’s episode: How Jason traded corporate burnout for financial freedom with real estate The “SMART” investor’s framework for analyzing real estate deals How to properly vet sponsors and syndication deals before committing capital Why so many secondary markets are ripe with multifamily investing opportunities How operators can stand out in today’s high-interest-rate environment — Novo Capital Management Connect with Jason on LinkedIn 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. 0:00 Buying Back Your Time 6:29 The "SMART" Framework 15:19 Re-rank Your Markets 25:21 When to Walk Away 30:10 Value-Add Apartment Deals 33:15 Pivoting to Multifamily 35:19 Best Opportunities in 2026 40:49 Connect with Jason!
- Apr 27, 202620 min
Real Deals: A $10M Win by Taking on This “Complex” Parking Garage Deal
This single property created more than $10M in value, but it was the most complex real estate deal we’ve ever done. We had to put a million dollars at risk to even start the transaction—and it was non-refundable. Multiple buyers, a cross-collateralized property in receivership with a parking lot, a hotel, and office space. This wasn’t going to be easy, but it definitely paid off. Today, I’m peeling back the curtain, showing you the full numbers and story of this commercial real estate case study that proves if you put in the work, the reward is there—and it could be an eight-figure payoff. I’ll walk through how we got this off-market, underpriced property sent to us, how we found buyers to take over the parts of the property we had no interest in, the substantial non-refundable earnest money we had to put down to close, and the hiccup at the eleventh hour that almost completely killed the deal. Plus, I’ll share exactly what we did to take this parking garage investment from $31M to $35M to now being worth north of $40 million. This is how we did it. Insights from today’s episode: A full real estate case study of the most complex deal we’ve ever done Why I put a seven-figure non-refundable deposit on a property that had low chances of closing How we immediately walked into $4 million of equity from purchase The value-add improvements we made to grow this property’s value by over $10 million The #1 reason why a broker sent this off-market deal to us before anyone else How we subdivided and sold parts of the property while we were buying it Our exact loan structure (LTV, debt, terms) to reduce risk — Investing in Parking Lots: Real Estate’s #1 Overlooked Opportunity | Ep. 977 Charlotte Parking Facility Case Study 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. 0:00 Intro 1:38 Off-Market Broker Deal 4:11 You CANNOT Beat This! 5:20 This Could Have Killed It 11:23 $4M in Instant Equity 12:36 Adding Value Immediately
- Apr 20, 202645 min
Developing a $140M “Passion Project” to Turn Dirt Into a Community Dream
For many real estate investors, development is the next level of property investing. Instead of renovating, you’re building from the ground up, turning dirt into something hundreds or even thousands of people will use daily. But how do you start, get in good graces with the local government, and build projects you can be truly proud of? Kristi Kandel went from zero development experience to running her own office in a year, with undeniable success. She built 30 Family Dollar locations in one of the hardest markets in America—California. But that’s not all—she even took on extraordinarily complex projects like building hydrogen fueling stations, something most developers wouldn’t even dare to entertain. She’s done some of the hardest development jobs and is sharing exactly how you can get your foot in the door, from planning what to build based on your market, to getting the local government on your side, who should be developing, and the mistake that almost cost her millions. Plus, Kristi shares details on the $140M passion project she’s building with public-private partnerships—the kind of legacy project every investor dreams of. Insights from today’s episode: How to get into real estate development, even if you have no experience The first thing to check before you plan on developing any piece of land The one person you must get in contact with to get the city’s approval One big utility mistake that could have cost Kristi’s team millions of dollars How locals can develop in their own communities and stop outside builders from taking over The one project Kristi says was impossible to finish—and swears she'll never do again — Connect with Kristi on LinkedIn Follow Kristi on Instagram 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 WHAT to Build 05:46 New City? Find This Person 08:05 Where Deals Get "Stuck" 14:14 Starting in THE Hardest Market 18:39 What She's Building Now 21:17 Developing YOUR Community 29:13 $140M Passion Project 35:40 This Mistake Could Have Cost Millions 43:43 Connect with Kristi!
- Apr 13, 202650 min
Senior Housing’s Inflection Point: Demand is Quickly Outpacing Supply
Senior living investments are at a critical inflection point. Demand is sharply rising as the Baby Boomer generation ages, but supply hasn’t kept pace. The “silver tsunami” is starting to send waves our way, and skilled operators are already taking advantage. Value-add senior living investments, like the example shared by today’s guest, are seeing values multiply—and diligent operators have huge opportunities not only to make sizable returns but also to provide better lives for their residents. Lynn Jerath, founder of Citrine Investment Group, has a battle-tested background in REIT investing, hospitality, multifamily, and real estate private equity. She’s pivoted to senior housing investments not only because of the profit potential, but also because of the purpose behind them. And she’s not just buying managerially distressed assets, flipping the operator, and walking away. Lynn’s team is delivering significant value add and, as a result, increasing the facility's value by 2x–3x on their total investment. She says demand is still growing while supply is constrained—and this trend could accelerate. Between independent living, assisted living, memory care, and active adult investments, Lynn proves (with real numbers) that this space is far from saturated as the silver surge begins to wash ashore. Insights from today’s episode: Real return numbers on senior living investments as Lynn operates heavy value-add improvements Why senior living has a long road ahead as demand grows and supply stagnates Thinking of going from multifamily to senior living? Lynn has crucial advice to share The #1 way to get more senior living residents in your community Most popular niches of senior living (and their current cap rates) Lynn’s exact buy box for senior living investments—what has to work for her to buy — Connect with Lynn on LinkedIn Citrine Investment Group 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. 00:00 Intro 01:54 Senior Living is a Different Ballgame 07:18 Undersupplied with Growing Demand? 13:59 Why Senior Living CAN'T Be Replaced 21:15 Big Players Are Getting In 24:52 Value-Add Senior Living in 2026 28:12 Case Study (2Xing Value) 31:07 How to Value-Add Senior Living 35:27 Getting New Residents 37:44 Most Popular Niches (and Cap Rates) 42:05 Lynn's Buy Box 47:55 It's About More Than Money 49:39 Connect with Lynn!
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About Real Estate Investing for Cash Flow with Kevin Bupp
There are a lot of real游戏副本 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 gener游戏副本ional 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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