Real Estate Investing for Cash Flow with Kevin Bupp

He Left Goldman Sachs to Bring Residential Real Estate to “Normal” Investors | Ep. 994

36 min · 29. juni 2026
episode He Left Goldman Sachs to Bring Residential Real Estate to “Normal” Investors | Ep. 994 cover

Description

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 lower the barrier to entry and bring these opportunities down to the average person. In 2022, that dream became a reality when he launched Mogul, a real estate investing platform that allows users to buy fractional shares of residential properties in a matter of clicks. Think Airbnbs in vacation markets, quadplexes with long-term tenants, and even single-family homes that are rented by the room. With new offerings weekly, investment minimums of just $250, and all the benefits of direct ownership—but without any of the normal landlord responsibilities—everyday people can now buy affordable shares of rental properties in top markets across the U.S. Whether you’re a seasoned investor or just beginning your journey, this conversation will challenge what you thought was possible with real estate investing and the resources required to build real, long-term wealth. Insights from today’s episode: * Why Alex left Goldman Sachs to start a fractional real estate investing platform * How to reap all the benefits of rental property ownership without being a landlord * The Mogul “model” that delivers higher annual returns than many REITs * Residential real estate opportunities with $250 investment minimums * The high-ROI real estate markets Alex and his team are targeting across the Sun Belt — Connect with Alex on LinkedIn [https://www.linkedin.com/in/alex-blackwood-a3996a135]   Mogul [https://www.mogul.club/] Recommended Resources: * 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, click here [http://investwithkb.com/?utm_source=podcast&utm_medium=shownotes&utm_campaign=rei4cf&utm_content=ep994] for opportunities to invest in real estate projects alongside Kevin and his team.  * Accredited Investors, you’re invited to Join the Cash Flow Investor Club [https://kevinbupp.com/join/] 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 [https://kevinbupp.com/join/]! * Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com [http://kevinbupp.com/].  * Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast [http://kevinbupp.com/Podcast]. 00:00 Intro 01:21 What Is the Mogul "Model"? 06:22 Managing the Properties 09:06 High-ROI Sun Belt Markets 16:03 Mogul Property Performance 21:50 Advantages Over REITs 26:28 Weathering the Airbnb "Storm" 34:03 Investing with $250! 35:26 Connect with Alex!

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episode How to Lock in 99 Years of Cash Flow (Today) with Commercial Ground Leases | Ep. 997 artwork

How to Lock in 99 Years of Cash Flow (Today) with Commercial Ground Leases | Ep. 997

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. Danielle Ash, partner and co-chair of the ground lease practice at Adler & Stachenfeld, has helped countless investors generate predictable cash flow, preserve long-term ownership, and even unlock trapped equity with this often-overlooked strategy. She unpacks the three main “buckets” of ground leases, along with the sale-leaseback option that allows owner-operators to create liquidity for other projects. Danielle also shares a real-world case study involving a New York City property with massive potential and a $200 million renovation, managed and paid for by the lessee.  Whether the goal is to free up capital for future acquisitions or create a long-term passive income stream while benefitting from capital improvements, the ground lease is a powerful tool worth exploring. Insights from today’s episode: * How to create long-term cash flow with commercial ground leases * A real case study of a New York City ground lease deal involving a $200 million renovation (paid by the lessee!) * The biggest risks to consider before entering into a ground lease agreement * Why a ground lease is often a win-win for both owner and operator * What lenders look for when underwriting ground lease tenants * How owner-operators can create liquidity through sale-leasebacks

20. juli 202642 min
episode How to Fund Your Next Commercial Real Estate Deal with USDA Financing | Ep. 996 artwork

How to Fund Your Next Commercial Real Estate Deal with USDA Financing | Ep. 996

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 Blanchard, commercial lending expert and co-founder of X-Caliber Rural Capital. With more than 30 years of banking and lending experience, Jordan has built a career out of helping investors unlock borrowing opportunities—like USDA financing—many don’t realize exist. Jordan unpacks the loan’s biggest advantages and trade-offs while dispelling the biggest misconceptions surrounding it. He also shares exactly what investors need to know before applying, as well as how to layer other financing options and tax credits into an efficient capital stack. There’s no sugarcoating it: USDA loans can be difficult to qualify for. But for investors needing large amounts of capital, flexible terms, and a lower-money-down alternative to conventional financing, the payoff is well worth it. Insights from today’s episode: * USDA loans—how they work, who they’re for, and common misconceptions * How to quickly determine if you’re eligible for a USDA loan * USDA versus SBA versus conventional financing (pros and cons) * The ideal capital “stack” for funding commercial real estate deals * Inside the $185 million deal Jordan and his team recently closed * The five most common reasons why operators default on commercial loans 00:00 Intro 03:05 USDA Lending 101 08:12 2 Common Misconceptions 11:52 Longer, More Flexible Terms 14:36 Creating Your Capital "Stack" 21:20 Who Is USDA-Eligible? 22:55 Biggest Investor Mistakes 32:08 5 Rapid-Fire Questions! 35:42 Connect with Jordan! — Connect with Jordan on LinkedIn [https://www.linkedin.com/in/x-caliberruralcapital]   X-Caliber Rural Capital [https://x-calibercap.com/] Email Jordan at jordanb@xrcusda.com Recommended Resources: * 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, click here [http://investwithkb.com/?utm_source=podcast&utm_medium=shownotes&utm_campaign=rei4cf&utm_content=ep996] for opportunities to invest in real estate projects alongside Kevin and his team.  * Accredited Investors, you’re invited to Join the Cash Flow Investor Club [https://kevinbupp.com/join/] 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 [https://kevinbupp.com/join/]! * Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com [http://kevinbupp.com/].  * Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast [http://kevinbupp.com/Podcast]. Disclaimer: This podcast is for educational purposes only and does not constitute financial, tax, or legal advice. Consult with a qualified professional before making any investment decisions.

13. juli 202637 min
episode She Oversees $150M Acquisitions: Here’s What “Smart” Operators Are Doing Today w/Hannah Hammond artwork

She Oversees $150M Acquisitions: Here’s What “Smart” Operators Are Doing Today w/Hannah Hammond

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 commercial mortgage brokerage HB Capital, has a unique vantage point on this dynamic. Through thousands of relationships with operators and lenders nationwide, she sits at the intersection of capital markets and commercial real estate investing. Not to mention, Hannah has scaled her own multimillion-dollar residential real estate portfolio. But the principles that guide her investment decisions today were shaped by more than market cycles. Raised in a family that struggled financially, Hannah believed money was the key to peace, happiness, and opportunity. This was only partially true. What she discovered after quitting corporate America for entrepreneurship, starting multiple businesses, and achieving financial freedom was that real “wealth” had much more to do with a life rooted in flow, not force. In today’s conversation, she shares about the painful experiences that shaped her, lessons from failed partnerships, and why the “disciplined” investors from a few years ago are the ones capitalizing on opportunities emerging from market distress. Insights from today’s episode: * Hannah’s personal journey from financial hardship to financial freedom * Why Hannah quit her comfortable engineering career to go all-in on real estate * Lessons learned from failed partnerships and risky private lending experiences * How Hannah’s engineering background has influenced her underwriting and risk tolerance * The three fatal mistakes that cause operators to go underwater on assets * Why true wealth stems from being fully aligned with your values and purpose—not money * How to craft a daily routine that allows you to live through flow, not force —   Connect with Hannah on Instagram [https://www.instagram.com/hannahbhammond]   HB Capital [https://www.hbcapitalre.com/] Recommended Resources: * 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, click here [http://investwithkb.com/?utm_source=podcast&utm_medium=shownotes&utm_campaign=rei4cf&utm_content=ep995] for opportunities to invest in real estate projects alongside Kevin and his team.  * Accredited Investors, you’re invited to Join the Cash Flow Investor Club [https://kevinbupp.com/join/] 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 [https://kevinbupp.com/join/]! * Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com [http://kevinbupp.com/].  * Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast [http://kevinbupp.com/Podcast]. 00:00 From Scarcity to Abundance 04:09 Quitting Corporate at 21 06:15 Where Operators Are Winning 12:17 Inside the Phoenix Market 18:56 Taking "Calculated" Risks 21:59 Learning from Loss & Failure 25:44 Launching HB Capital 30:08 Attracting Top Talent 34:58 What Is Real "Wealth"? 41:18 Hannah's Daily Routine 45:43 The Next 5 Years 49:36 Connect with Hannah! Disclaimer: This podcast is for educational purposes only and does not constitute financial, tax, or legal advice. Consult with a qualified professional before making any investment decisions.

6. juli 202650 min
episode He Left Goldman Sachs to Bring Residential Real Estate to “Normal” Investors | Ep. 994 artwork

He Left Goldman Sachs to Bring Residential Real Estate to “Normal” Investors | Ep. 994

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 lower the barrier to entry and bring these opportunities down to the average person. In 2022, that dream became a reality when he launched Mogul, a real estate investing platform that allows users to buy fractional shares of residential properties in a matter of clicks. Think Airbnbs in vacation markets, quadplexes with long-term tenants, and even single-family homes that are rented by the room. With new offerings weekly, investment minimums of just $250, and all the benefits of direct ownership—but without any of the normal landlord responsibilities—everyday people can now buy affordable shares of rental properties in top markets across the U.S. Whether you’re a seasoned investor or just beginning your journey, this conversation will challenge what you thought was possible with real estate investing and the resources required to build real, long-term wealth. Insights from today’s episode: * Why Alex left Goldman Sachs to start a fractional real estate investing platform * How to reap all the benefits of rental property ownership without being a landlord * The Mogul “model” that delivers higher annual returns than many REITs * Residential real estate opportunities with $250 investment minimums * The high-ROI real estate markets Alex and his team are targeting across the Sun Belt — Connect with Alex on LinkedIn [https://www.linkedin.com/in/alex-blackwood-a3996a135]   Mogul [https://www.mogul.club/] Recommended Resources: * 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, click here [http://investwithkb.com/?utm_source=podcast&utm_medium=shownotes&utm_campaign=rei4cf&utm_content=ep994] for opportunities to invest in real estate projects alongside Kevin and his team.  * Accredited Investors, you’re invited to Join the Cash Flow Investor Club [https://kevinbupp.com/join/] 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 [https://kevinbupp.com/join/]! * Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com [http://kevinbupp.com/].  * Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast [http://kevinbupp.com/Podcast]. 00:00 Intro 01:21 What Is the Mogul "Model"? 06:22 Managing the Properties 09:06 High-ROI Sun Belt Markets 16:03 Mogul Property Performance 21:50 Advantages Over REITs 26:28 Weathering the Airbnb "Storm" 34:03 Investing with $250! 35:26 Connect with Alex!

29. juni 202636 min
episode Industrial Real Estate Did the Last Thing He Expected (And It Made Him Wealthy) | Ep. 993 artwork

Industrial Real Estate Did the Last Thing He Expected (And It Made Him Wealthy) | Ep. 993

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 sluggish rent growth. In the industrial space, the opposite happened. As new construction came to a screeching halt in many of Joel’s markets, supply constraints drove rents higher, particularly for many of his class-B investments. But that’s just the most recent cycle. Joel’s thesis has been tested repeatedly throughout his 40-plus-year career, and he’s survived it all—not because he’s immune to failure, but because he stuck to fundamentals while the syndicators around him played with fire and got burned. His no-debt model has made raising capital significantly more challenging, but it’s also helped him weather storms that have wiped out riskier investments. Joel doesn’t use unrealistic pro forma to gain an edge. Instead, he focuses on mitigating risk, playing the long game, and hunting down off-market opportunities most operators don’t have the patience to pursue. It’s helped him win strong deals—and it could help you do the same. Insights from today’s episode: * Why industrial real estate has outperformed other asset classes in many markets * The three biggest red flags Joel avoids on industrial real estate deals * The economic factors that caused industrial rents to double in the last four years * Creating an edge in your market with off-market investing opportunities * Why location and size matter more than the purchase price of industrial buildings * The conservative approach to leverage that gives you more staying power — Hear Our Last Interview with Joel Connect with Joel on LinkedIn [https://www.linkedin.com/in/joel-friedland]   Brit Properties [https://www.britproperties.com/] Recommended Resources: * 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 [http://investwithkb.com/?utm_source=podcast&utm_medium=shownotes&utm_campaign=rei4cf&utm_content=ep993] for opportunities to invest in real estate projects alongside Kevin and his team.  * Accredited Investors, you’re invited to Join the Cash Flow Investor Club [https://kevinbupp.com/join/] 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 [https://kevinbupp.com/join/]! * Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com [http://kevinbupp.com/].  * Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast [http://kevinbupp.com/Podcast]. 00:00 Intro 02:00 What Happened to Industrial? 10:20 Creating an Edge 14:37 Joel's "Problem" Property 15:29 The 4 D's 27:46 Managing LP Expectations 35:39 The No-Debt Investing Model 50:48 Biggest Deal "Killers" 54:58 Connect with Joel!

22. juni 202657 min