Real Estate Investing for Cash Flow with Kevin Bupp

Just over five years ago, express car washes were peaking. Private equity was getting in, ready to buy up these cash-flowing projects at high prices. At this moment, Ben Salzberg and Bill Kanatas knew it was time to get out and pivot toward an even more durable asset.

What did they turn to? Self-storage, and not your average mom-and-pop shop. Class-A, climate-controlled, multi-story facilities that self-storage REITs could easily come in and run. It’s a blueprint that has worked for them for five years plan, consult, construct, and let the 3rd-party self-storage management team take care of the rest. But there’s much more to this strategy than building a pretty box.

On today’s show, Ben and Bill outline the exact blueprint they use to build REIT-ready self-storage facilities, how to work with big names (Public Storage, Extra Space, CubeSmart) before you lay a single brick, what to look for in a market before you decide to build, and why entitling land, turning dirt into dollars is more worth it than you think. Plus, Ben and Bill share the optimal storage facility size (and demand ratios) so you know what REITs and customers want.

Insights from today’s episode:

• A REIT-ready self-storage development blueprint from 30-year development veterans
• The 3rd-party self-storage management that instantly plugs into your facility 
• Why Ben and Bill left cash-flowing car washes for class-A self-storage facilities 
• Signs a market is too saturated with self-storage (and what to look for instead)
• Getting the city on your side—how to create a win-win for local government, residents, and your investment 
• Entitling land—is it worth the effort to turn raw dirt into a buildable lot?

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Connect with Ben on LinkedIn

Connect with Bill on LinkedIn

Work with Self Storage Developers 

Email Self Storage Developers: [email protected] 

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/Podcas

Every multifamily operator wants to know how to increase NOI, but they’re not doing it the right way. Traditional renovations leading to rent increases have been harder to get right in the past few years. But what if there was a “hidden” source of not only higher revenue but also lower expenses—something 99% of operators are unaware of, that could increase NOI by tens of thousands per month.

Today, Bill Douglas of OpticWise (https://www.opticwise.com/) and Marcy Sagel of MSA Interiors (https://msainteriors.com/), CRE technology and design experts, join us to talk about the NOI levers nobody is thinking of pulling. We’ll share the actual amenities and tactics you can use today in your building to attract higher-paying tenants and turn utility expenses into revenue, with game changing effects on your bottom line. Plus, what buy-and-hold vs. short term flip investors must include in their budget to get the maximum NOI possible. 

One amenity our experts say is an actual waste of money…unless you hear how to monetize it properly. 

Retrofitting an older vintage multifamily? Bill and Marcy share exactly how to track which design changes are working for your bottom line, how to go from antiquated to next-level tech, and the hidden value-add opportunities you can implement starting today. Plus, why your property management company could be stopping you from making tens of thousands more every month! 

Insights from today’s episode:

• The “hidden” NOI opportunities that most multifamily operators completely miss 
• One amenity you can provide that could increase your revenue $80-$90 PER unit
• The design tweaks younger renters require that move the needle on NOI 
• An expert checklist on renovating and retrofitting 1980s vintage to today’s standards 
• Data you can start collecting now that shows precisely what tenants want/don’t 
• The best piece of advice for anyone building a new multifamily (could boost your NOI) 
  

Connect with Bill on LinkedIn (https://www.linkedin.com/in/billdouglas/)

OpticWise (https://www.opticwise.com/)

Grab Bill’s Book, Peak Property Performance (https://www.peakpropertyperformance.com/)

Listen to Bill’s Peak Property Performance Podcast (https://podcasts.apple.com/us/podcast/peak-property-performance/id1817250978)

Connect with Marcy on LinkedIn (https://www.linkedin.com/in/marcysagel/)

MSA Interiors (https://msainteriors.com/)

Recommended Resources:

• Accredited Investors, you’re invited to Join the Cashflow 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/)!
• 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.

What does it take to go from growing up in a mobile home…to owning hundreds of mobile home lots across the country? Today’s guest, my business partner Brian Spear, is living proof that mindset and mission matter more than where you start.

In this episode, Brian shares his remarkable journey into mobile home park investing, the lessons from the wealthy that helped him build long-term success, and how we joined forces to build Sunrise Capital Investors—with mobile home park investments totaling in the hundreds of millions.

We go deep on what makes buying a mobile home park such a powerful wealth-building tool, the character traits that separate long-term winners from short-term speculators, and how we’ve used investing as a vehicle for something more than just financial gain.

This isn’t just an investing episode—it’s a blueprint for building both cash flow and character.

Insights from today’s episode:

• How Brian went from tenant to owner in the mobile home park space
• Lessons from the wealthy that can reshape how you approach investing
• Why "burning the boats" is essential if you want to succeed
• Why mobile home park investing remains a recession-resistant strategy
• The power of delayed gratification, frugality, and compounding wisdom
• What it means to pass down wisdom—not just wealth

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Connect with Brian on LinkedIn

Listen to The Sage Investor Podcast

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.

More syndications are going sideways. Capital calls have become common. Tensions are rising between operators and investors…but not for all deals. If you had talked to today’s guest before forming your real estate syndication, there’s a good chance you’d already have a battle plan for every potential challenge. Thankfully, today, CRE’s go-to legal advisor is sharing his take for free.

Richard Crouch has worked on eight figure commercial real estate deals for over two decades, helping advise on disputes, defaults, and structuring. He’s the one who sets up your failsafes before a deal goes sideways and advises you on the right way to resolve it once the damage has been done.

Today, we’re getting into the nitty-gritty that not only sponsors but also passive investors need to know. We’ll talk about the “gotcha” clauses lenders can use to extract fees from you or worse…take your entire property, the right way to handle a capital call so your exit strategy doesn’t fall apart, and what to do in the unfortunate event that a guarantor passes away mid-deal. 

Insights from today’s episode:

• Your lender is not your friend: the “gotchas” put in place that you must navigate around 
• How to handle capital calls so your investors don’t feel neglected and unsettled 
• One thing you need to include in every single operating agreement you sign 
• A crucial event that can “trigger” if a guarantor passes away during a deal cycle 
• Opportunity for buyers: Is now the time to invest in distressed debt amid inexperienced syndicators' struggles

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Connect with Richard on LinkedIn

Richard’s Email: [email protected] 

Richard’s Phone Number: 757-353-0969

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.

2025 is about to be in the books, and for many real estate investors, it was a challenging year. But at Sunrise Capital, it’s been a year of massive growth, disciplined pivots, and, for me, purpose: my wife and two sons. 

We’ve acquired $80,000,000 in new assets this year—irreplaceable real estate that we couldn’t pass up. We’ve had to step away from other deals when the numbers didn’t pencil, and in the end, we’re monumentally proud of what we’ve accomplished.

So what’s next? I have a big announcement at the end of this episode—and this is the first time I’m going public with it. My life, and the lives of my family, are about to change as we do something I’ve been dreaming about for over a decade. This is what it was all for.

But before that, I’ll share the lessons we learned in 2025 that shaped our business and buying decisions, why capital raising wasn’t as hard as many sponsors think it is (if you operate the way we do), and why we didn’t have to change our underwriting during some of the most challenging years of investing in decades.

I’m sharing the wins and losses, both personal and professional, on today’s show. Thank you for a wonderful 2025. 2026 is going to be a little…different. 

Insights from today’s episode:

• A huge announcement that has been over a decade in the making 
• How we acquired $80M in irreplaceable assets and raised the money for it in 2025
• The discipline you need to walk away from a deal that goes sideways (you won’t regret it)
• How to raise capital the right way, and why you should stop selling yourself (and your deals) so hard
• The commitments I’m making in 2026 (you can keep me accountable!) 

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.

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

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Connect with Joe on LinkedIn

Email Joe: [email protected]

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!

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?

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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!

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!

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 stepped in to manage (and buy) foreclosed properties that were barely staying afloat.

Through 20 years of multifamily experience, he's pinpointed the most overlooked markets in the country, how to dodge rent control and get your own city government to actively fight against it, and the #1 mistake you can make when screening tenants. He's sharing it all, plus his key multifamily metric, in this episode.

Insights from today's episode:

The one screening metric Joe uses to determine if a multifamily investment is worth it What to do when one of your tenants turns your building into a rave venue An underrated area of the country that multifamily investors shouldn't ignore A sign that you're managing your portfolio inefficiently (and it could cost you) Why Joe's team is moving into new development for even greater returns

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Connect with Joe on LinkedIn

East Superior Real Estate Partners

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!

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: https://www.granitetowersequitygroup.com/

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 wins."

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.