The Opportunity You’ve Never Heard of in CRE (“IOS” Real Estate)
Real Estate Investing for Cash Flow with Kevin Bupp
Release Date: 12/01/2025
The Painful Failure That Pushed Me to Pivot (and Made Me Millions) w/Joe Downs
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...
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Skip the Sunbelt: Why “Micropolitan” Multifamily Markets are Unbeatable w/Cory Jacobson
Real Estate Investing for Cash Flow with Kevin Bupp
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...
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The Opportunity You’ve Never Heard of in CRE (“IOS” Real Estate)
Real Estate Investing for Cash Flow with Kevin Bupp
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...
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The Most Underrated Metric in Multifamily (Not Cap Rate/Cash Flow) w/Joe Root
Real Estate Investing for Cash Flow with Kevin Bupp
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...
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#962 Former Pro Snowboarder Dan Brisse’s Playbook for Durable Multifamily
Real Estate Investing for Cash Flow with Kevin Bupp
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: 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...
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#961 Affordability Rates & the New-Build Advantage with Keith Weinhold
Real Estate Investing for Cash Flow with Kevin Bupp
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: Highlights: 03:10 - Affordability Squeeze — Inflation, prices, and rates 5:05 - Sales Volume Drop 09:15 - Rates In Context ...
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#960 Why Discipline Beats Deals: Lee Yoder’s Real Estate Journey
Real Estate Investing for Cash Flow with Kevin Bupp
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: 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...
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#959 Payments to Properties: Charles Carillo’s B-Class Multifamily Playbook
Real Estate Investing for Cash Flow with Kevin Bupp
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: Highlights: 02:00 - Startup → Real Estate 04:00 - Flipping...
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#958 Hard Assets, Smart Money: MOB riches, safe leverage & the 2025–26 opportunity
Real Estate Investing for Cash Flow with Kevin Bupp
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: Highlights: 04:45 - First Deal...
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#957 House Hacks & Mobile Home Parks: Build a 7-Figure Portfolio
Real Estate Investing for Cash Flow with Kevin Bupp
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: Email: Highlights: 5:00 — Turning a Park Around 11:00 — House Hacking 101 18:00 — Lessons from Passive...
info_outlineThis 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.
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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/
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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!