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Real Estate Investing for Cash Flow with Kevin Bupp

Real Estate Investing for Cash Flow with Kevin Bupp

Kevin Bupp 998 Episodes Aug 17, 2026

This podcast focuses on commercial real estate investing for cash flow and generational wealth, moving beyond residential fix-and-flips. Host Kevin Bupp interviews industry experts on topics like multifamily apartments, syndication, and passive income. The show aims to help both new and experienced investors scale their real estate businesses.

Episodes

The State of Affordable Housing in 2026 w/ BOXABL CEO Galiano Tiramani | Ep. 1001
The State of Affordable Housing in 2026 w/ BOXABL CEO Galiano Tiramani | Ep. 1001 Aug 17, 2026 1343 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 enteri
The Keys to a Tax-Efficient Real Estate Exit (1031 Exchanges, DSTs, & More) | Ep. 1000
The Keys to a Tax-Efficient Real Estate Exit (1031 Exchanges, DSTs, & More) | Ep. 1000 Aug 10, 2026 2404 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 pa
50 Years and 100+ Real Estate Development Deals: What I’ve Learned | Ep 999
50 Years and 100+ Real Estate Development Deals: What I’ve Learned | Ep 999 Aug 3, 2026 3022 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 au
Real Deals: 15% Above Projections on a “Risky” Deal Everyone Else Passed Up
Real Deals: 15% Above Projections on a “Risky” Deal Everyone Else Passed Up Jul 27, 2026 1407 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 ma
How to Lock in 99 Years of Cash Flow (Today) with Commercial Ground Leases | Ep. 997
How to Lock in 99 Years of Cash Flow (Today) with Commercial Ground Leases | Ep. 997 Jul 20, 2026 2529 Imagine owning a property with enormous upside, but one that’s operationally complex and requires hundreds of thousands or even millions in capital improvements. What do you do? Selling leaves value on the table. A joint venture dilutes control and introduces unnecessary risk. So what’s the alternative? One of commercial real estate’s most underutilized capital structures: the ground lease. Daniel
How to Fund Your Next Commercial Real Estate Deal with USDA Financing | Ep. 996
How to Fund Your Next Commercial Real Estate Deal with USDA Financing | Ep. 996 Jul 13, 2026 2264 When investors hear the term USDA loan, they tend to picture small towns, farmland, and niche financing. In reality, they may be overlooking one of the best—and least understood—government-backed loan programs available for commercial real estate. In many cases, the USDA loan is an even better option than both the SBA loan and conventional financing. To explain why, we’re joined by Jordan Blancha
She Oversees $150M Acquisitions: Here’s What “Smart” Operators Are Doing Today w/Hannah Hammond
She Oversees $150M Acquisitions: Here’s What “Smart” Operators Are Doing Today w/Hannah Hammond Jul 6, 2026 3024 The real estate investors who are thriving in today’s market are the ones who ignored the pressure to buy questionable deals during the boom years. While many operators fell for floating-rate debt, banked on unrealistic rent growth, and underwrote for best-case scenarios, a more “patient” group focused on the fundamentals. Hannah Hammond, founder and CEO of the capital advisory firm and commercia
He Left Goldman Sachs to Bring Residential Real Estate to “Normal” Investors | Ep. 994
He Left Goldman Sachs to Bring Residential Real Estate to “Normal” Investors | Ep. 994 Jun 29, 2026 2194 Real estate has arguably been the largest wealth generator in history, but for many years, most opportunities have been out of reach for those without large bank accounts. Alex Blackwood is on a mission to change that with fractional real estate. While working at Goldman Sachs’ private equity group and delivering 15%-20% annual returns to investors, he started dreaming of a company that would lowe
Industrial Real Estate Did the Last Thing He Expected (And It Made Him Wealthy) | Ep. 993
Industrial Real Estate Did the Last Thing He Expected (And It Made Him Wealthy) | Ep. 993 Jun 22, 2026 3445 Industrial real estate might look simple from the outside. You buy a large box, lease it out, and collect rent. But like with any asset, you can lose your shirt just as easily as you can make a fortune. Joel Friedland, founder of Brit Properties, understands this better than most. Two years ago, he and his team were bracing for another industry lull, largely driven by high interest rates and slug
Pioneering a Prudent Path in Industrial Real Estate | [Replay Ep. 686 ]
Pioneering a Prudent Path in Industrial Real Estate | [Replay Ep. 686 ] Jun 22, 2026 2566 Before you check out episode 993, get up to speed with Building a Resilient Industrial Portfolio: Lessons from Joel Friedland. In this episode, Joel Friedland, founder of Brit Properties and seasoned industrial real estate operator, shares his journey of transforming his investment philosophy after the lessons learned from the 2008 financial crisis. Discover how a focus on risk control, no debt st
What $100M Institutional Investors Look for Before Cutting the Check | Ep. 992
What $100M Institutional Investors Look for Before Cutting the Check | Ep. 992 Jun 15, 2026 3163 Many real estate operators assume institutional capital is simply retail capital at a larger scale: fewer investors, bigger checks. It’s not. What they’re missing is that institutional capital often requires you to build more infrastructure, create tighter procedures, and relinquish some control of the asset itself. The question is: Is the consolidation you get from institutional capital worth
Top U.S. Universities Have a $1T Real Estate “Problem” (And He’s Solving It)
Top U.S. Universities Have a $1T Real Estate “Problem” (And He’s Solving It) Jun 9, 2026 2122 Most investors chase opportunities in familiar asset classes like multifamily, self-storage, or mobile home parks, but today’s guest has carved out a narrow lane within the industry: university-aligned real estate investing. America’s top universities are facing a $1 trillion infrastructure problem over the next decade, and to continue attracting top talent, they need upgraded facilities and amen

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