Don’t Get Wiped Out: The Multifamily Investing Strategy That Beat 3 Downturns | Ep. 988

Real Estate Investing for Cash Flow with Kevin Bupp

Kevin Bupp

Business, Investing, Education

4.8 • 679 Ratings

🗓️ 18 May 2026

⏱️ 39 minutes

🔗️ Recording | iTunes | RSS

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Summary

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!

Transcript

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0:00.0	The 2000.com bubble, the 2008 financial crisis, and the 2022 interest rate shocks.
0:06.8	What do all these have in common?
0:09.0	Today I'm joined by Dwight Dunton, founder of Bonaventure, a vertically integrated real estate platform that has quietly built one of the largest multifamily portfolios finance through the HUD program in the entire country.
0:20.2	The lessons he learned surviving everything from drywall nails through the 2008 financial crisis is why he built multiple operating businesses around his portfolio, not for growth, but to eliminate what he calls wipeout risk. So if you're serious about building a business that lasts through multiple cycles, then you're going to get a lot out of this one. Let's get into it. Dwight, welcome to the show, my friend. It's a pleasure to have you here with us today. Hey, thanks, Kevin. I'm excited to be here with you and your audience. I'm probably take you back in time here. We'll hop into DeLorean and go back in time. You know, you jumped straight, I guess what I would say, you jumped straight into the deep end at 25 years old, buying
0:56.3	your first multifamily property, a 378 unit property. And so let's start there. I think
1:02.1	that will help set the baseline for the conversation here today. I guess, first and foremost,
1:06.2	I guess what did you see in that net deal, that first large deal that you did that everyone
1:10.1	else completely missed?
1:11.6	Great question.
1:12.6	It was definitely the deep end.
1:14.6	Thankfully, I didn't drown.
1:15.6	I also wouldn't be here today.
1:17.6	But, you know, the backstory was that property, our family had originally owned the land in 1960,
1:26.6	a large real estate conglomerate built an apartment building,
1:29.4	and we collected checks for 40 years. And so, you know, we weren't actively involved, but I
1:33.9	certainly knew the property. It was in my hometown of Alexandria, Virginia. And we went to a
1:39.2	owner's meeting, which was basically a regional property manager, who proceeded for two hours
1:45.1	to sell us that this was a terrible property in a sea location that needed $5 million
1:50.5	of capital improvements, and you'd get no return. That was just to keep the lights on. And what I
1:55.5	saw was a couple things. One, I knew the neighborhood. Like, I grew up in that town. It was not a terrible location.
2:01.7	It was not a terrible property.
2:03.1	Two, I knew we didn't have $5 million to invest.
	...

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