From Zero to 1,200+ Multifamily Units in 7 Years (Replacing His W2 Income) | Ep. 986

Real Estate Investing for Cash Flow with Kevin Bupp

Kevin Bupp

Investing, Education, Business

4.8 • 679 Ratings

🗓️ 4 May 2026

⏱️ 42 minutes

🔗️ Recording | iTunes | RSS

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Summary

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!

Transcript

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0:00.0	Joining me today is Jason Kenny of Novo Capital Management. Jason entered real estate like many before him and built his portfolio the hands-on way. In today's episode, we write down why he re-ranks markets every quarter. How he spots deals that look great but quietly fail at the sub-market level. In the framework, he uses to protect capital when others are stretching. Jason, welcome to the Real Estate Investing for Cashlow podcast. It's
0:21.4	great to have you here with us today. And so I would love to, if we could, kick this off by
0:25.6	maybe giving the listeners for those that aren't familiar with you, you know, who you were before
0:29.5	Novo Capital actually started. My prior life was a corporate life. I spent about 20 years in
0:36.1	information technology, about 10 of those years in the medical industry,
0:40.6	about another 10 in financial services.
0:43.4	And my wife also has a corporate background.
0:45.9	And when we were younger, you know, we were just moving around the country, chasing
0:50.1	titles, chasing promotions, and trying to do the corporate thing.
0:56.3	Did that for a while. And life was good. We were earning a great living and having a good time, got to live in some
1:00.3	cool places. There was a stretch of time there. I think we lived in about five different states
1:05.2	in 10 years. So we were moving around a lot. The thing about that is it kind of burns you out after
1:10.2	a while. And when we started having a family, I think we had the realization that we weren't going to be
1:15.9	able to keep that pace up for a long time. And so we were looking to switch things up a little bit,
1:22.4	except we also had the realization at that time that we didn't really have the freedom and
1:27.0	flexibility that we thought
1:28.0	we had. We had spent years pursuing our corporate gigs, and we were earning a great living,
1:34.3	but all the income we had was tied to our W-2 jobs. And after we had our family, my wife wanted to
1:41.7	focus on being a mom, and we just, unfortunately, we're not in the
1:44.6	position to do that. About that time, we decided to make some changes, and we decided that we
1:50.3	were going to be a little bit more intentional with the incomes that we had built up. And we were
1:55.7	going to start acquiring assets that generated income for us. And for us, we thought that the best
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