Real Estate Investing for Cash Flow with Kevin Bupp

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

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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

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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

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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 

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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

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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!