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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 Sep 14, 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

He Walked Away Mid-Deal. It Cost Him $100,000 (But Saved His Investors)
He Walked Away Mid-Deal. It Cost Him $100,000 (But Saved His Investors) Sep 14, 2026 3078 Real estate investing demands conviction, but when market conditions shift—sometimes even mid-deal—do you stick to your guns or walk away?   August Biniaz, CIO and co-founder of CPI Capital, found himself toeing this exact line shortly after underwriting and raising capital for a large, build-to-rent community in Tucson, Arizona.   When interest rates spiked, the deal no longer penciled, but e
99% Passed on These Commercial Properties. They Made Him a Fortune.
99% Passed on These Commercial Properties. They Made Him a Fortune. Sep 7, 2026 2709 After more than 50 years in commercial real estate, Bill Cummings has built an 11-million-square-foot portfolio spanning 12 communities around Greater Boston. But he did so by ignoring many of the conventional rules of real estate investing. When his peers suggested he explore new markets, he stayed local. When others urged him to sell, he continued to hold for decades. And when other developers s
He Tripled His Cash Flow by Doing What Most Buy-and-Hold Investors Won’t | Ep. 1003
He Tripled His Cash Flow by Doing What Most Buy-and-Hold Investors Won’t | Ep. 1003 Aug 31, 2026 3368 Early on, most real estate investors are chasing the same thing: more. More properties. More units. More cash flow. But eventually, “more” becomes a trap.   Every acquisition brings new challenges and risks. At some point, the smartest move isn’t buying more. It’s pruning. Chris Lopez, co-founder of Property Llama and host of the PassivePockets podcast, argues that investors should act more like
How to Earn a 13%-18% Average Annual Return in 2026 (Tax Lien Investing 101) | Ep. 1002
How to Earn a 13%-18% Average Annual Return in 2026 (Tax Lien Investing 101) | Ep. 1002 Aug 24, 2026 3100 Tax liens are often pitched as a passive way to earn double-digit returns from investments that are backed by real estate. This is only half true. While these investments average 13%-18% annual returns, they may actually be one of the least passive investing strategies. With roughly 20 years of experience as a real estate investor, attorney, and title professional, Stephen Morel understands all th
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

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