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 self-storage has high demand, greater revenue, and a growing need in an increasingly entrepreneurial economy. 

Joe breaks down why he’s so excited about this new type of storage and shares the returns he’s making from running an incredibly lucrative “distressed debt” company. Plus, why investors are overlooking the wide open opportunity in small “mom and pop” real estate investments and how to “reinvent” yourself after failure puts you back at the starting line.

 

Insights from today’s episode:

  • The pivots that helped Joe build multiple million-dollar real estate businesses

  • Surprisingly high returns in the second mortgage note market (big investors can’t get in!)

  • Is everyone wrong about self-storage? Why this asset is actually undersupplied in much of the country 

  • Pro storage: the newest investing opportunity that is seeing a wave of demand 

  • Think you can’t start over in your 30s, 40s, or 50s? Joe will prove you wrong—and get you fired up

Connect with Joe on LinkedIn

Email Joe: joe@belroseam.com

Are you a high-net-worth investor with capital to deploy in the next 12 months? Build passive income and wealth by investing in real estate projects alongside Kevin and his team! 

Grab a copy of my latest book, The Cash Flow Investor! 

Listen to past podcast episodes! 

Direct download: EP96X_Joe_Downs_Podcast_Feed.mp3
Category:general -- posted at: 12:00am EST

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 managed a light renovation, walking away with a six-figure profit—three times his salary. That was it. For Cory, it was time to go all in.

Now, he’s putting his money into medium-sized multifamily investments (5-30 units) in “untapped” micropolitan markets and sharing his lessons on the Wealth Juice podcast. We talk about the perfect partnerships that have helped him scale at light speed, the day the “worst thing that could have happened” came true, and the actual markets he’s currently investing in.

 

Insights from today’s episode:

  • Why “micropolitan” multifamily markets beat top investing areas like the Sunbelt 

  • The single-best first investment a real estate investor should make (even on low income)

  • Real estate partnership splits and how to find a partner who offsets your weaknesses 

  • Never sell? Our biggest regrets when it comes to owning investment properties 

  • How to deal with the (inevitable) challenges of real estate investing (burned down and flooded rentals)

  • The real point of wealth—are you getting rich just to get bored? 

 

 

Connect with Cory on LinkedIn

Wealth Juice Podcast

Wealth Juice Instagram 

Are you a high-net-worth investor with capital to deploy in the next 12 months? Build passive income and wealth by investing in real estate projects alongside Kevin and his team! 

Grab a copy of my latest book, The Cash Flow Investor! 

Listen to past podcast episodes!

Direct download: EP965_Cory_Jacobson_v03.mp3
Category:general -- posted at: 12:00am EST

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 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. 

_______

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/ 

 

💰 _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 https://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_ : https://kevinbupp.com/the-cash-flow-investor/ 

 

🎧_Tap into a wealth of free information on Commercial Real Estate Investing_

 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!

Direct download: Truck-Parking-Investment-Industrial-Outdoor-Storage-EP964_Jake_Gusso.mp3
Category:general -- posted at: 12:00am EST

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