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Real Estate Investing for Cash Flow with Kevin Bupp

Buy the Dip (Without Getting Burned): How to Vet Sponsors Before Writing a Check

Real Estate Investing for Cash Flow with Kevin Bupp

Kevin Bupp

Investing, Education, Business

4.8679 Ratings

🗓️ 2 February 2026

⏱️ 28 minutes

🧾️ Download transcript

Summary

Everyone plans to “buy the dip” until it’s time to write the check. Multifamily opportunities are rising, and with properties 20%+ off the peak of pricing, investors are getting flooded with “deals.” But, like we learned over the past five years, the wrong sponsor (even with the right deal) can kill your returns and blow up the wealth you spent so long to build.  So, how do you spot the opportunities vs. the landmines in multifamily? We brought on fund of funds manager, Lon Welsh, to share his sponsor-vetting checklist.  With decades of experience in real estate investing, launching his capital fund in 2022 could have been disastrous (rising interest rates, rent growth freezes, expanding cap rates), but to this day, Lon has over a 90% success rate across funds within his own fund. This wasn’t done by guessing or gut-checks, but carefully choosing the right sponsor for the right deal. Today, Lon shares his own sponsor-vetting checklist, how he personally confirms a deal is worth getting into, the best multifamily markets in the country with easing supply, low regulation, and strong demand, and how to ensure a sponsor was intentional, not lucky, in achieving their past successes.  Plus, we even get Lon’s multifamily prediction for 2026-2027. Insights from today’s episode: How to vet a multifamily sponsor before putting a dollar into their deal Why a “fund of funds” could be the more diversified, safer bet than real estate syndications  What to look at to ensure a sponsor wasn’t just “lucky” during past deal cycles  The best places to invest in multifamily right now (2026) where supply is about to drop off How to feel confident buying during a dip when everyone else is too scared to act  Lon’s medical receivables play making passive income without a single property  — Connect with Lon on LinkedIn Ironton Capital 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.

Transcript

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0:00.0

Everybody says that they're a contrarian investor right up until it's time to write a check in a downturn.

0:05.0

And right now with multifamily trading at roughly 20% off the peak, the question isn't whether

0:09.7

or not there's opportunity. It's how do you buy this dip without blowing yourself up on the wrong

0:14.2

sponsor or on the wrong assumptions. Welcome back to the real estate investing for cash flow

0:18.5

podcast. I'm your host Kevin Bob, and this is

0:21.1

where active and aspiring investors get the real world playbooks from operators who are out there

0:25.8

in the field actually deploying capital today. And in today's show, we're going to be breaking

0:29.8

down the following. How a professional fund of funds manager vet sponsors in a market full of

0:34.8

uncertainty, where the real opportunities and landmines are in multifamily right now? And then also how diversification inside of a fund can turn one total loss into a balanced win. Lon, I'm excited to have you here to chat with you here today. But before I'd say before we dive into the meat potatoes of it all, maybe if you would, just take a moment or two and expand upon your background a little bit. Tell our listeners, Hugh, you are, who Ironton Capital is, and who you guys are built to serve. Yeah, my background. I worked in corporate finance for a couple of years, went back to business school. I worked as a strategy consultant for eight years at Deloitte and then Accenture, and then I've been in real estate full-time for a couple decades. I built a real estate brokerage from scratch,

1:11.2

which grew to be the largest independent in Colorado, built a title company, sold both of

1:16.0

those off in December of 21, right before the rates went up, and then launched Ironton Capital

1:21.3

in June of 22. I've been investing in real estate for a couple decades as a real estate

1:26.5

developer and a landlord, and basically were just taking the same strategy of what I've been doing for real estate for a couple decades as a real estate developer and a landlord,

1:28.5

and basically we're just taking the same strategy of what I've been doing for the last couple

1:31.5

decades and we're just doing at a larger scale.

1:34.3

And instead of just having a couple friends and family investing along with me, now I can bring

1:37.1

like 100 people at a time to invest along with me.

1:39.2

So it's worked out really well.

1:41.8

Most of the people that we serve are either really busy professionals. They have a lot of stock and bond investment. They want to have real estate exposure, but they don't want to buy a building. So this is an easy way for them to get that kind of diversified access. Or we have a lot of people who have been active investors for a long time. They've kind of gotten frustrated being an active landlord.

2:19.0

They're ready to be passive, but they still want the real estate exposure, and we can solve that problem for them. So that tends to be the two people we serve the most. 2022 launching the company then kind of a precarious time, right? Right for rates were kind of on their upswing. And so talk to me about that a little bit. I don't know what part of 2022. If rates had already started, you know, trending upwards. It was June.

2:19.5

Yeah, so, uh,

2:20.9

rates and or something. And so talk to me about that a little bit. I don't know what part of 2020, if rates had already started, you know, trending upwards.

...

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