Real Estate Investing for Cash Flow with Kevin Bupp

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!