Real Estate Investing for Cash Flow with Kevin Bupp

Most investors chase opportunities in familiar asset classes like multifamily, self-storage, or mobile home parks, but today’s guest has carved out a narrow lane within the industry: university-aligned real estate investing.

America’s top universities are facing a $1 trillion infrastructure problem over the next decade, and to continue attracting top talent, they need upgraded facilities and amenities. Josh Parker, founder, chairman, and CEO of Ancora, has built a business that collaborates with these anchor institutions to breathe new life into college towns throughout the U.S.

By creating strong ties with premier universities and forming strategic partnerships to access resources beyond just capital, Josh and his team have been able to bring economic stability to several disjointed communities. This level of specialization has allowed him to stand out at a time when other investors are swimming upstream against cutthroat competition and deteriorating margins.

Josh’s message isn’t for more investors to try their hand at complex urban redevelopment deals. Rather, it’s that there are just two ways to create an edge in today’s market: become the next Blackstone, or niche down and dig deep.

Insights from today’s episode:

• Josh’s journey into university-aligned real estate redevelopment
• Solving the $1 trillion problem that universities are facing over the next decade
• The two ways real estate operators can create an edge in today’s market
• Partnering with anchor institutions to revitalize “disjointed” communities
• Leveraging tax credits and government programs to offset development costs

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Connect with Josh on LinkedIn

Ancora

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 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 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!
• 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.

00:00 Intro

01:12 Strategic University Partnerships

05:31 Josh's "Lightbulb" Moment

09:43 The South Bend Project

13:22 The $1T Development "Gap"

19:04 Identifying Top Opportunities

23:40 Structuring the Capital Stack

30:04 Niching Down in Real Estate

34:18 Connect with Josh!

No matter how much you underwrite, budget, plan, and strategize, nothing ever goes exactly to plan. On our biggest mobile home park investment yet (700+ lots), we thought we had accounted for every obstacle that could have been thrown our way—boy, were we wrong. But with the right team, tactics, and pivots, we turned what many would have given up on into a property with close to $3M in annual NOI—and even more room to grow.

Welcome back to another case study episode, where I’m sharing real deals we’ve taken down at Sunrise Capital Investors, giving you an under-the-hood look at what went wrong, what went right, the real returns, and the money we spent. 

This time, we’re in Fort Wayne, Indiana, taking a look at Ridgebrook Hills mobile home park, a community of over 700 lots, hundreds of residents, and huge infrastructure. What was supposed to be a homerun from the start turned into a steady stream of challenges for multiple years, but ended up being a rock-solid property we’re proud to own with huge upside. 

I’m sharing all the challenges, budgets, and real return numbers in this episode so you can dodge some of the headwinds we hit along the journey. 

Insights from today’s episode:

• How we landed a massive mobile home park by being disciplined when others were on buying sprees
• The real NOI numbers from this hugely improved mobile home park investment 
• The upside and value-add potential you can unlock with mismanaged mobile home parks 
• The staffing disaster that almost brought this deal to a halt (on day three!)
• An expense many investors overlook (we did!) that can cost you six-figures per year 
• The one thing that saved this deal (every investor or investment team needs this)

— Check Out our Free Guide on Investing in Mobile Home Parks!

Full Ridgebrook Hills MHP Case Study 

Real Deals: A $10M Win by Taking on This “Complex” Parking Garage Deal | Ep. 985

Recommended Resources:

• Accredited Investors, you’re invited to Join the Cash Flow 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.

Landlord insurance has slowly become a major cost for many operators. After 2020, insurance prices began to rise rapidly, and making a claim became even harder when disaster struck. For many operators, it feels like throwing tens of thousands, if not hundreds of thousands of dollars, into the furnace every year, for a benefit you’ll rarely use. And who stands to profit from it? Insurance companies.

But an overlooked insurance structure is becoming increasingly common among operators, saving them 20% on their premium costs and sometimes even making them a profit on insuring their properties. 

Nicolas Lares, CEO of Insur3Tech, worked as an insurance agent for years before ever hearing of "captive insurance” or “risk pooling.” When the small businesses he was tasked with insuring were being priced out so badly they could barely operate, he began building alternative structures, all federally backstopped, but without the middlemen. 

Now, Nicolas’s clients are profiting from their insurance investment, getting premiums on average 20% lower, and getting claims paid out in a matter of days, not weeks. 

How would your NOI improve if one of your greatest costs became a profit driver?

Insights from today’s episode:

• The “risk pooling” insurance model that drops your insurance cost significantly 
• How to get paid to pay your premium (the insurance company actually pays Nicolas’s clients)
• Who can (and should) opt for "captive insurance” instead of the traditional route  
• The real reason why your landlord insurance premium is so high (it’s making insurance companies billions)
• How do these alternative providers make money without baking in a profit margin? 

—

Connect with Nicolas on LinkedIn

Insur3Tech

Recommended Resources:

• Accredited Investors, you’re invited to Join the Cash Flow 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.

00:00 Insurance Is Broken in 2026

03:40 They're Making Billions off of Us

06:19 Cutting Out the Middlemen

11:58 The Insurance "Pool" Structure

16:23 Getting Paid to Insure Your Property

19:33 Who Can (and Should) Do This?

26:28 How Do THESE Providers Make Money?

31:15 Work with Nicolas!

What do the 2000 dot-com crash, the 2008 Great Financial Crisis, and the 2022 interest rate shock have in common? They wiped many multifamily operators out.

Dwight Dunton survived all three.

As founder and CEO of Bonaventure, Dwight and his team are responsible for $2.8 billion in assets under management (AUM). But Dwight didn’t start a fund, raise capital, and figure it out as he went. He learned to grow and protect his own money first.

At just 25 years old, while his peers chased flashy internet stocks, Dwight acquired a 378-unit apartment community. He was stepping into a struggling asset that demanded sizable improvements and millions in repairs, but this experience provided a crash course in operations, value-add investing, and asset management.

Dwight says to become an old, rich investor, you’ve got to 1. get old and 2. not get wiped out along the way. So, he focuses on “asymmetric” investing opportunities that have capped downside but plenty of upside for good operators. Then, he further de-risks these assets by insourcing the things most operators would outsource.

In today’s conversation, we discuss all of this—the power of vertical integration, protecting assets and capital through downturns, and why long-term, buy-and-hold investing remains the surest path to generational wealth.

Insights from today’s episode:

• How Dwight protects his assets and capital with “anti-wipeout” investing
• The keys to building a business that can survive any “Black Swan” event
• Acquiring and managing a 378-unit apartment community at 25 years old
• How to dramatically improve revenue with vertical integration
• Why supply constraint, not job growth, is the surprising main driver of multifamily success

—

Connect with Dwight on LinkedIn

Bonaventure

Internet Subway

Vest Residential

Recommended Resources:

• Accredited Investors, you’re invited to Join the Cash Flow 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.

00:00 Intro

00:45 Buying 370+ Units at 25

07:09 Surviving (& Winning) in 2008

11:17 Don't Get Wiped Out!

18:12 Buy-and-Hold (Forever!)

23:20 Vertical Integration 101

32:40 What's Next for Dwight?

37:27 Connect with Dwight!

When new technology emerges, the biggest winners aren’t the headline watchers or the reluctant investors. Rather, it’s those who already control the infrastructure when that technology becomes mainstream who profit most.

The next major infrastructure wave? Advanced air mobility. It’s not a matter of if, but when private aircraft become the next popular mode of travel in the United States, and Lisa Wright, founder of Landings, will be waiting at the runway when it arrives.

With decades of experience as a commercial real estate architect, Lisa is asking the question most people aren’t thinking of just yet: where will these aircraft actually land?

As an early adopter, Lisa’s company is currently in a race to develop over 2,000 vertiport sites over the next five years. With little more than angel investments and bootstrapping, her team has already secured two-year land lease options throughout many rural communities where these amenities are likely to appear.

In today’s conversation, Lisa shares the strategy that has helped her stay fluid without major capital raises, her long-term vision for building out a coast-to-coast vertiport network, and the revenue-share model that gives landowners an almost irresistible investing opportunity.

Insights from today’s episode:

• Lisa’s five-year plan for developing a 2,000-site vertiport network
• How early adopters of advanced air mobility stand to profit in the years ahead
• Why private aviation is poised to become the new frontier of transportation
• The revenue-share model that gives rural landowners unique investing opportunities
• Creating multiple revenue streams with low-cost, low-maintenance landing sites

—

Connect with Lisa on LinkedIn

Landings

Recommended Resources:

• Accredited Investors, you’re invited to Join the Cash Flow 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.

00:00 The Spark for Landings

00:50 Intro

02:23 Why Private Aviation?

07:36 eVTOL Is Already Here

12:21 "Viable" Vertiport Sites

19:15 Costs & Revenue Share

25:19 How Does It Make Money?

27:09 Lisa's 5-Year Plan

30:58 Funding Vertiport Development

33:54 Connect with Lisa!

Many investors talk about financial freedom, but few ever scale to the point where they can leave their W-2 jobs and live off the cash flow from their real estate investments.

Jason Kenney did it. Completely burned out after two decades of climbing the corporate ladder, Jason and his wife started allocating their W-2 income to real estate assets with the goal of buying back their time. Within only a few years, Jason was able to quit his W-2 job and replace his income with cash-flowing investments.

Now, as the founder of Novo Capital Management, Jason focuses exclusively on multifamily apartments, with a 1,200-unit portfolio spanning several markets.

Having been on both sides of syndications, Jason offers a rare, dual perspective on operations and the process of vetting sponsors. Using his “SMART” framework, investors can do their own due diligence on general partners, syndication deals, and even active investments.

In this conversation, Jason shares about some of his recent acquisitions, candid lessons from deals that didn’t pencil, and what investors need to do to truly stand out in today’s high-interest-rate environment.

Insights from today’s episode:

• How Jason traded corporate burnout for financial freedom with real estate
• The “SMART” investor’s framework for analyzing real estate deals
• How to properly vet sponsors and syndication deals before committing capital
• Why so many secondary markets are ripe with multifamily investing opportunities
• How operators can stand out in today’s high-interest-rate environment

—

Novo Capital Management

Connect with Jason on LinkedIn

Recommended Resources:

• Accredited Investors, you’re invited to Join the Cash Flow 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.

0:00 Buying Back Your Time

6:29 The "SMART" Framework

15:19 Re-rank Your Markets

25:21 When to Walk Away

30:10 Value-Add Apartment Deals

33:15 Pivoting to Multifamily

35:19 Best Opportunities in 2026

40:49 Connect with Jason!

This single property created more than $10M in value, but it was the most complex real estate deal we’ve ever done. We had to put a million dollars at risk to even start the transaction—and it was non-refundable. Multiple buyers, a cross-collateralized property in receivership with a parking lot, a hotel, and office space. This wasn’t going to be easy, but it definitely paid off. 

Today, I’m peeling back the curtain, showing you the full numbers and story of this commercial real estate case study that proves if you put in the work, the reward is there—and it could be an eight-figure payoff. 

I’ll walk through how we got this off-market, underpriced property sent to us, how we found buyers to take over the parts of the property we had no interest in, the substantial non-refundable earnest money we had to put down to close, and the hiccup at the eleventh hour that almost completely killed the deal.

Plus, I’ll share exactly what we did to take this parking garage investment from $31M to $35M to now being worth north of $40 million. This is how we did it.

Insights from today’s episode:

• A full real estate case study of the most complex deal we’ve ever done 
• Why I put a seven-figure non-refundable deposit on a property that had low chances of closing 
• How we immediately walked into $4 million of equity from purchase 
• The value-add improvements we made to grow this property’s value by over $10 million 
• The #1 reason why a broker sent this off-market deal to us before anyone else 
• How we subdivided and sold parts of the property while we were buying it 
• Our exact loan structure (LTV, debt, terms) to reduce risk 

—

Investing in Parking Lots: Real Estate’s #1 Overlooked Opportunity | Ep. 977

Charlotte Parking Facility Case Study 

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.

0:00 Intro
1:38 Off-Market Broker Deal
4:11 You CANNOT Beat This!
5:20 This Could Have Killed It
11:23 $4M in Instant Equity
12:36 Adding Value Immediately

For many real estate investors, development is the next level of property investing. Instead of renovating, you’re building from the ground up, turning dirt into something hundreds or even thousands of people will use daily. But how do you start, get in good graces with the local government, and build projects you can be truly proud of?

Kristi Kandel went from zero development experience to running her own office in a year, with undeniable success. She built 30 Family Dollar locations in one of the hardest markets in America—California. But that’s not all—she even took on extraordinarily complex projects like building hydrogen fueling stations, something most developers wouldn’t even dare to entertain.

She’s done some of the hardest development jobs and is sharing exactly how you can get your foot in the door, from planning what to build based on your market, to getting the local government on your side, who should be developing, and the mistake that almost cost her millions. 

Plus, Kristi shares details on the $140M passion project she’s building with public-private partnerships—the kind of legacy project every investor dreams of. 

Insights from today’s episode:

• How to get into real estate development, even if you have no experience 
• The first thing to check before you plan on developing any piece of land 
• The one person you must get in contact with to get the city’s approval
• One big utility mistake that could have cost Kristi’s team millions of dollars
• How locals can develop in their own communities and stop outside builders from taking over 
• The one project Kristi says was impossible to finish—and swears she'll never do again

—

Connect with Kristi on LinkedIn

Follow Kristi on Instagram 

Recommended Resources:

• Accredited Investors, you’re invited to Join the Cash Flow 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.

00:00 WHAT to Build

05:46 New City? Find This Person

08:05 Where Deals Get "Stuck"

14:14 Starting in THE Hardest Market

18:39 What She's Building Now

21:17 Developing YOUR Community

29:13 $140M Passion Project

35:40 This Mistake Could Have Cost Millions

43:43 Connect with Kristi!

Senior living investments are at a critical inflection point. Demand is sharply rising as the Baby Boomer generation ages, but supply hasn’t kept pace. The “silver tsunami” is starting to send waves our way, and skilled operators are already taking advantage. Value-add senior living investments, like the example shared by today’s guest, are seeing values multiply—and diligent operators have huge opportunities not only to make sizable returns but also to provide better lives for their residents.

Lynn Jerath, founder of Citrine Investment Group, has a battle-tested background in REIT investing, hospitality, multifamily, and real estate private equity. She’s pivoted to senior housing investments not only because of the profit potential, but also because of the purpose behind them. And she’s not just buying managerially distressed assets, flipping the operator, and walking away.

Lynn’s team is delivering significant value add and, as a result, increasing the facility's value by 2x–3x on their total investment. She says demand is still growing while supply is constrained—and this trend could accelerate. 

Between independent living, assisted living, memory care, and active adult investments, Lynn proves (with real numbers) that this space is far from saturated as the silver surge begins to wash ashore. 

Insights from today’s episode:

• Real return numbers on senior living investments as Lynn operates heavy value-add improvements 
• Why senior living has a long road ahead as demand grows and supply stagnates 
• Thinking of going from multifamily to senior living? Lynn has crucial advice to share 
• The #1 way to get more senior living residents in your community 
• Most popular niches of senior living (and their current cap rates) 
• Lynn’s exact buy box for senior living investments—what has to work for her to buy  

—

Connect with Lynn on LinkedIn

Citrine Investment Group

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.

00:00 Intro

01:54 Senior Living is a Different Ballgame

07:18 Undersupplied with Growing Demand?

13:59 Why Senior Living CAN'T Be Replaced

21:15 Big Players Are Getting In

24:52 Value-Add Senior Living in 2026

28:12 Case Study (2Xing Value)

31:07 How to Value-Add Senior Living

35:27 Getting New Residents

37:44 Most Popular Niches (and Cap Rates)

42:05 Lynn's Buy Box

47:55 It's About More Than Money

49:39 Connect with Lynn!

Mobile home parks are often labeled “recession-proof,” and it’s largely true. They were some of the most resilient assets throughout the Great Financial Crisis, when single-family homes, multifamily apartments, and most other asset classes saw deep distress.

But what is it about mobile home parks that make them seemingly “safe,” and is there a catch?

Jack Martin, co-founder and CIO of 52TEN, was investing in real estate before, during, and after the 2008 housing market crash, and the fallout caused him to reconsider where he wanted to invest for the next 10, 20, or 30 years.

In this episode, he shares exactly why he pivoted from multifamily apartments to “safer,” more recession-resistant mobile home parks, and delivers crucial advice on gauging market demand, “conservative” underwriting, and scaling your investments in today’s market.

The truth is, mobile home parks are strong investments, but only with good operators. Those who understand the asset, market, and tenant dynamics usually stay profitable—even in a worst-case scenario. But those who underwrite mobile home parks just like they would any other real estate asset are in for a rude awakening.

Insights from today’s episode:

• Why Jack exited multifamily apartments for mobile home parks after 2008
• Why mobile home parks are more “recession-proof” than other asset classes
• Practical ways to gauge mobile home park demand in a new market
• The three biggest challenges mobile home park investors face in 2026
• Why “cheaper” is rarely better when buying a mobile home park

—

Connect with Jack on LinkedIn

52TEN

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.

0:00 Intro

0:58 Jack's Investing Journey

3:52 The Fallout of 2008

10:17 Pivoting to Mobile Home Parks

18:14 "Recession-Proof" Assets

28:10 Gauging Market Demand

36:19 "Painful" Lessons Learned

48:33 Connect with Jack!