Real Estate Investing for Cash Flow with Kevin Bupp

The fear of failure stops many from ever getting into real estate. But what if it's the failures that actually make you wealthy? Today's guest woke up in his 30s, broke and burned out, having traded years of his life for a business that went belly up. What looked like a failure to everyone else was the start of a multimillion-dollar business empire for Joe Downs. Joe has invested in it all—rental properties, flips, self-storage, mortgage notes, industrial warehouses, and more—but his newest obsession is one much of the market knows nothing about: pro storage. This new wave of self-storage has high demand, greater revenue, and a growing need in an increasingly entrepreneurial economy. Joe breaks down why he's so excited about this new type of storage and shares the returns he's making from running an incredibly lucrative "distressed debt" company. Plus, why investors are overlooking the wide open opportunity in small "mom and pop" real estate investments and how to "reinvent" yourself after failure puts you back at the starting line. Insights from today's episode: The pivots that helped Joe build multiple million-dollar real estate businesses Surprisingly high returns in the second mortgage note market (big investors can't get in!) Is everyone wrong about self-storage? Why this asset is actually undersupplied in much of the country Pro storage: the newest investing opportunity that is seeing a wave of demand Think you can't start over in your 30s, 40s, or 50s? Joe will prove you wrong—and get you fired up — Connect with Joe on LinkedIn Email Joe: joe@belroseam.com Are you a high-net-worth investor with capital to deploy in the next 12 months? Build passive income and wealth by investing in real estate projects alongside Kevin and his team! Grab a copy of my latest book, The Cash Flow Investor! Listen to past podcast episodes!

While most operators chase the Sunbelt states, one overlooked market type is making small- and mid-sized multifamily investors wealthier. It's got near-zero vacancy, with strong employment anchors, and durable cash flow thanks to consistent demand. They're not big cities; instead, they're what today's guest calls "micropolitan" areas—top multifamily markets even the most experienced investors overlook. While making just $35,000 per year, Cory Jacobson made the best move a small investor can make—he bought a house, rented out the rooms, and lived for free. On his second deal, he managed a light renovation, walking away with a six-figure profit—three times his salary. That was it. For Cory, it was time to go all in. Now, he's putting his money into medium-sized multifamily investments (5-30 units) in "untapped" micropolitan markets and sharing his lessons on the Wealth Juice podcast. We talk about the perfect partnerships that have helped him scale at light speed, the day the "worst thing that could have happened" came true, and the actual markets he's currently investing in. Insights from today's episode: Why "micropolitan" multifamily markets beat top investing areas like the Sunbelt The single-best first investment a real estate investor should make (even on low income) Real estate partnership splits and how to find a partner who offsets your weaknesses Never sell? Our biggest regrets when it comes to owning investment properties How to deal with the (inevitable) challenges of real estate investing (burned down and flooded rentals) The real point of wealth—are you getting rich just to get bored? — Connect with Cory on LinkedIn Wealth Juice Podcast Wealth Juice Instagram Are you a high-net-worth investor with capital to deploy in the next 12 months? Build passive income and wealth by investing in real estate projects alongside Kevin and his team! Grab a copy of my latest book, The Cash Flow Investor! Listen to past podcast episodes!

This could be one of the, if not the, most under realized opportunities in commercial real estate. It's a blue ocean market operating in a boring business space that most investors (and service providers) are completely overlooking. But, Jake Guso tapped into what no other real estate investor knew about industrial outdoor storage management, specifically truck parking lot businesses. These mom-and-pop shops are running almost entirely on handwritten notes and Zelle payments and it's an absolute mess for owners and their accountants. After managing multiple truck parking lot businesses himself, Jake built Rig Hut, the software platform that turns dirt lots into cash flow. So much so that, in one case study, Jake helped an owner increase his annual revenue by as much as six figures. Today, I'm sitting down with Jake to talk about how Rig Hut is industrializing truck parking, how investors can get into the game themselves (and make serious money), the shocking "11-to-1" statistic that would make any investor excited, and how this forgotten asset class is only one of many in the CRE space. Plus, I'll even share my exact strategy for finding deals like this in any area of the country. _______ Connect with Jake on LinkedIn: https://www.linkedin.com/in/jake-guso-16bb167a/ Rig Hut: https://www.therighut.com/ Rig Hut Facebook: https://www.facebook.com/profile.php?id=100084019464551 Rig Hut Instagram: https://www.instagram.com/therighut Rig Hut TikTok: https://www.tiktok.com/@righuttruckparking Rig Hut X/Twitter: https://x.com/truckpark_king Sunrise Capital Case Studies: https://sunrisecapitalinvestors.com/case-studies/ 💰 _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 https://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_ : https://kevinbupp.com/the-cash-flow-investor/ 🎧_Tap into a wealth of free information on Commercial Real Estate Investing_ Listen to past podcast episodes: https://kevinbupp.com/Podcast/ Chapters: 00:00 Intro 03:01 The 11-to-1 Statistic 06:57 Who Can Do This? 09:58 Scaling in a "Blue Ocean" Market 12:01 Massively Overlooked Opportunity? 16:33 Six-Figure Revenue Jump Overnight 20:57 Software Costs and Pricing 22:01 Long-Term Plans 23:57 How to Get Started with Truck Parking 30:30 Connect with Jake!

One key metric could tell you immediately whether a multifamily real estate investment is worth buying—but most people ignore it. It's not cash flow, it's not cap rate, and it's probably something you've overlooked dozens of times. Joe Root helped grow his family's multifamily portfolio and manages over 100 properties using this metric. Joe left the glitz of a corporate Wall Street career when he realized his family's apartment portfolio was better than the big city life. Multifamily management quickly became his new obsession. During the Great Financial Crisis of 2008, Joe stepped in to manage (and buy) foreclosed properties that were barely staying afloat. Through 20 years of multifamily experience, he's pinpointed the most overlooked markets in the country, how to dodge rent control and get your own city government to actively fight against it, and the #1 mistake you can make when screening tenants. He's sharing it all, plus his key multifamily metric, in this episode. Insights from today's episode: The one screening metric Joe uses to determine if a multifamily investment is worth it What to do when one of your tenants turns your building into a rave venue An underrated area of the country that multifamily investors shouldn't ignore A sign that you're managing your portfolio inefficiently (and it could cost you) Why Joe's team is moving into new development for even greater returns — Connect with Joe on LinkedIn East Superior Real Estate Partners Are you a high-net-worth investor with capital to deploy in the next 12 months? Build passive income and wealth by investing in real estate projects alongside Kevin and his team! Grab a copy of my latest book, The Cash Flow Investor! Listen to past podcast episodes!

Pro snowboard legend turned operator Dan Brisse breaks down how obsession and discipline translate to durable multifamily returns covering capital calls, bridge debt pain, why he's buying newer B+/A- locations, and where the next great deals are hiding. Connect with Daniel: https://www.granitetowersequitygroup.com/ Highlights: 1:50 - Daniel's Pro Snowboarding career 11:45 - Daniel's Wake up call 15:00 - Shift Your Mindset, Daniel's Specialty 20:39 - The Multifamily Landscape shift 26:59 - What to Buy Today Quote: "Obsession leads to greatness. In snowboarding or real estate, committed behavior over a long time wins." 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.

The housing market isn't broken, it's shifting. And smart investors are shifting with it. Keith Weinhold returns to explain why affordability is squeezed, why owners aren't selling, and why prices remain stubbornly strong despite lower sales volume. He also reveals where the numbers still pencil, which markets offer real yield, and why new construction is becoming one of the most overlooked investor opportunities right now. Connect with Kieth: https://getricheducation.com/ Highlights: 03:10 - Affordability Squeeze — Inflation, prices, and rates 5:05 - Sales Volume Drop 09:15 - Rates In Context 11:30 - Lock-In Effect 19:40 - New-Build Edge — Builder rate buydowns + lower insurance 33:10 - FHA Fourplex Play Quote: "The best use of your dollar isn't making your money work, it's making other people's money work: the bank's, the tenants', the government's." 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.

Physical therapist turned investor Lee Yoder breaks down how he left a stable W-2, lived below his means, and scaled from a duplex to 800+ units in six years. We cover flipping vs. cash-flow rentals, the JV to syndication leap, deal discipline, and why he brought property management in house to operate better and grow faster. A clear roadmap for anyone eyeing the jump from career to full time real estate. Connect with Lee: https://www.linkedin.com/in/lee-yoder-25793215a/ Highlights: 4:35 — Golden Handcuffs 7:40 — 30% Pay Cut 13:30 — First 34 Units 16:05 — All-In Runway 30:05 — Vertical Integration Quote: "You can buy any property you want if you pay the highest price. The discipline is stopping where your numbers say stop." 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.

Charles Carillo founder of Harborside Partners and host of the Global Investors Podcast joins Kevin to share how he went from building a billion dollar payments company to scaling a B-class multifamily portfolio. He breaks down lessons from early flips, why he exited C-class, refinancing a floating rate deal, and how he's underwriting acquisitions again amid tighter debt and flat rents. Practical, no-hype insights on buying right, protecting downside, and playing the long game in today's market. Connect with Charles: https://harborsidepartners.com/ Highlights: 02:00 - Startup → Real Estate 04:00 - Flipping Lessons 10:00 - Shift to B-Class 13:00 - Refinancing Floating 24:00 - Debt Reality Quote: "Real estate is a long-term play—early cash flow is modest, and you really see the fruits when you refinance or sell." 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.

Ben Reinberg is the Founder and CEO of Alliance CGC. Ben's journey began in accounting and has since grown into a commercial real estate career with decades of experience building and managing a diverse portfolio. Under Ben's leadership, Alliance has grown into a firm recognized nation wide for its focus on medical, retail, industrial, office, and multi family properties. Today, we'll dive into Ben's roots, what fuels Alliance's success, market trends shaping the future, and the challenges, and opportunities on the horizon. Connect with Ben: https://www.benreinberg.com/ Highlights: 04:45 - First Deal Lessons 13:40 - Why Medical Office 21:15 - Multifamily Distress Plays 25:05 - Leverage & Risk Lesson 37:20 - Mindset: "This Shall Pass" Quote: "Commercial real estate is a marathon. Your edge is the ability to hold, not the size of your leverage." 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.

Jordan Moorehead is a real estate power house who has built a diverse and impressive portfolio across multiple asset classes. Jordan Moorhead is a Louisville native, licensed sales agent in Texas, licensed broker in Minnesota, and an active rental property investor who now calls Austin, Texas home. He currently owns over 94 rental units, including mobile home parks, single-family rentals, and multi family properties acquired using the BRRRR strategy. Connect with Jordan: https://www.themoorheadteam.com/agents/jordan-moorhead/ Email: jordan.moorehead@kw.com Highlights: 5:00 — Turning a Park Around 11:00 — House Hacking 101 18:00 — Lessons from Passive Investing Mistakes 25:00 — Avoid Investor Pitfalls 28:00 — Future of the Mobile Home Park Industry Quote: "I love mobile home parks because you can give hardworking people a great place to live and still make a solid profit, it's a business that just feels good to run." 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.