Real Estate Investing for Cash Flow with Kevin Bupp

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

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!

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!

Mobile home parks are often labeled “recession-proof,” and it’s largely true. They were some of the most resilient assets throughout the Great Financial Crisis, when single-family homes, multifamily apartments, and most other asset classes saw deep distress. But what is it about mobile home parks that make them seemingly “safe,” and is there a catch? Jack Martin, co-founder and CIO of 52TEN, was investing in real estate before, during, and after the 2008 housing market crash, and the fallout caused him to reconsider where he wanted to invest for the next 10, 20, or 30 years. In this episode, he shares exactly why he pivoted from multifamily apartments to “safer,” more recession-resistant mobile home parks, and delivers crucial advice on gauging market demand, “conservative” underwriting, and scaling your investments in today’s market. The truth is, mobile home parks are strong investments, but only with good operators. Those who understand the asset, market, and tenant dynamics usually stay profitable—even in a worst-case scenario. But those who underwrite mobile home parks just like they would any other real estate asset are in for a rude awakening. Insights from today’s episode: Why Jack exited multifamily apartments for mobile home parks after 2008 Why mobile home parks are more “recession-proof” than other asset classes Practical ways to gauge mobile home park demand in a new market The three biggest challenges mobile home park investors face in 2026 Why “cheaper” is rarely better when buying a mobile home park — Connect with Jack on LinkedIn 52TEN 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 0:58 Jack's Investing Journey 3:52 The Fallout of 2008 10:17 Pivoting to Mobile Home Parks 18:14 "Recession-Proof" Assets 28:10 Gauging Market Demand 36:19 "Painful" Lessons Learned 48:33 Connect with Jack!

Over the last few years, many real estate investors learned a painful lesson: a polished pitch deck and impressive projections don’t guarantee a “safe” investment. Deals went south, capital got stuck, and naturally, passive investors are now far more cautious about where they deploy their hard-earned money. Sarah Miskelly, founder of Hylee Capital, has witnessed this shift firsthand. Today, smart limited partners are no longer chasing flashy pro formas. They want risk-mitigated, institutional-grade opportunities that once felt out of reach for everyday investors. At the same time, there’s been a growing shift toward debt investments, many of which Sarah believes aren’t nearly as safe as they appear. Sarah shares how she evaluates sponsors and syndication deals through both the “hard” and “soft” sides of due diligence, along with the red flags she watches for—mistakes that have burned countless LPs in the past. She also breaks down the return metrics that matter most to hands-off investors and highlights the most compelling opportunities emerging in today’s housing market—from multifamily apartments to mobile home parks. Insights from today’s episode: Sarah’s step-by-step process for vetting operators and syndication deals The return metrics that matter most to passive investors in today’s market Why many LPs are moving toward debt investments (that aren’t as safe as advertised) How to build a resilient portfolio by blending high-IRR deals and steady cash flow How building multiple cash flow streams can lead to greater lifestyle freedom — Connect with Sarah on LinkedIn Hylee 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. 0:00 Intro 0:49 Total Lifestyle Freedom 9:02 Better "Hands-Off" Investments 10:54 Operator Red Flags 18:54 What Has Changed? 22:39 LPs Are Being "Cautious" 28:44 Playing "the Long Game" 37:00 2026's Biggest Opportunities 40:49 Connect with Sarah!