Real Estate Investing for Cash Flow with Kevin Bupp

• #959 Payments to Properties: Charles Carillo’s B-Class Multifamily Playbook

  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.

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• #958 Hard Assets, Smart Money: MOB riches, safe leverage & the 2025–26 opportunity

  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.

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• #957 House Hacks & Mobile Home Parks: Build a 7-Figure Portfolio

  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: [email protected] 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.

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• #956: Understand The Power of Corporate Sale-Leasebacks

  Karly Iacono is a Senior Vice President in CBRE’s Capital Markets, Investment Properties group, specializing in the acquisition and disposition of net-lease assets and large portfolio transactions nationwide. She’s a recognized expert incorporate sale-lease back structuring, multi-tenant retail investments, and development advisory where she guides both institutional and private clients through complex deals. Additionally, she’s the host of the popular 'Commercial Real Estate Now’ podcast where she shares expert insights on the news and trends shaping the commercial real estate landscape. We deep into corporate sale-lease backs, the what, how, and why. Exploring how this powerful tool can benefit both companies and investors alike. Connect with Karly: https://www.cbre.com/, [email protected]  Highlights: 2:00 — What Is a Sale-Leaseback 4:00 — Tax & Capital Advantages 06:00 — Top Industries Using It 11:00 — Credit Drives Cap Rates 17:00 — Finding the Right Investment Quote: “A sale-leaseback isn’t just a way to sell real estate, it’s a strategic tool to unlock capital, fuel growth, and strengthen your business for the long term.”   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.

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• #955 FBF: Shifting Perspectives: How Dyslexia Inspired a Serial Entrepreneur, Designer, Solar Farm Expert, & Real Estate Giant

  Today's Flash Back Friday episode is from #732 that originally aired on Apr. 22, 2024. Jerry Rosengarten is a Brooklyn-born serial entrepreneur whose greatest skill is the extraordinary ability to perceive form and structure and opportunity from within disorder, including developing products to deal with dyslexia, reimagining real estate, and investing early and heavily in solar energy. Jerry's first big win came in the 1970s with the Leisure Suit, which became a cultural fashion phenomenon that stoked his confidence and staked his growing desire to build land mark New York projects like the Lofts and the The Bowery Hotel. Today, Jerry owns one of the largest private solar farms in the Northeast, located on Long Island's eastern tip, and his creative passions are focused on environmental stewardship and active advocacy for those suffering from learning disabilities. Highlights:  5:25 - Starting the famous Leisure Suit / Lessons Learned 12:22 - Finding a Creative Space (property) 20:22 - Making The Worst location in NY Successful 26:23 - Growing Up with Dyslexia / Seeing Things Differently 34:26 - The Importance of a Supportive Spouse Quote: "I jump on the train and take it to the end. Each-train are concepts are designs." Connect with Gerald: jumponthetrain.com   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.

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