About Real Estate Investing for Cash Flow with Kevin Bupp
There are a lot of real estate podcasts out there, most of which focusing on the residential fix and flips or wholesaling, but Kevin Bupp believes there's a smarter way to build long term cash flow and generational wealth. On the Real Estate Investing For Cash Flow podcast, you'll learn firsthand how the most successful commercial real estate investors in the world have learned to leverage their multifamily and commercial properties to create a steady stream of passive income. We'll spend time with industry experts who will teach you how to take your Real Estate Investing business to the next level.
Whether you're a brand new Real Estate investor or someone who's looking to make the transition into bigger and more profitable deals, this is the show for you. This is where the BIG BOY RE Investors come to play...ARE YOU READY?
On our show, we'll feature industry experts and discuss topics such as:
* Commercial Real Estate Investing
* How to get started
* Creating Passive Income from CRE
* Syndication
* Retail Shopping Centers
* Mobile Home Parks
* Medical Office
* Multifamily Apartments
* Industrial
* Office
* Self Storage
* Industrial
* 1031 exchanges
* Development
* Investing via your self directed IRA
* Private Lending
* How to buy your first commercial property
* And much, much , more
7,500+ Multifamily Units (and Huge Returns) by Going Where Most Operators Won’t | Ep. 1010
The Northeast and Mid-Atlantic regions are notoriously difficult to invest in due to heightened regulations, longer timelines, and a general lack of supply. Matt Frazier, founder of Jones Street Investment Partners, sees these barriers differently: as a competitive advantage.
While many investors steer clear of these areas entirely—flocking instead to regions like the Sun Belt, where there’s plenty of new supply and far less regulatory risk—Matt and his team are actively going against the grain. Headquartered in Boston, Massachusetts, their vertically integrated private equity firm manages close to 8,000 apartment units exclusively in and around their own backyard.
Their contrarian thesis centers on a fundamental supply-and-demand imbalance. In the Northeast, new inventory rarely comes online by comparison, limiting supply enough to not only drive property values higher but also keep rent growth ticking upward year after year.
In our conversation, Matt shares his firm’s approach to navigating these barriers, structuring capital in today’s high-interest-rate environment, the local “edge” they have over long-distance operators, and what the next five years might hold for Jones Street and its investors.
Insights from today’s episode:
Why many operators avoid investing in the Northeast and Mid-Atlantic regions
How Jones Street scaled its business amid regulatory risk and longer timelines
Why vertical integration creates a meaningful advantage in most markets
How “good” real estate deals can be derailed by the wrong capital structure
The main differences between using retail and institutional capital
—
Jones Street Investment Partners
Connect with Matt on LinkedIn
Recommended Resources:
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, click here for opportunities to invest in real estate projects alongside Kevin and his team.
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!
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.
Chapters:
00:00 Intro
01:20 Why the Northeast?
06:22 Multifamily Case Studies
10:30 Jones Street's "Local" Edge
18:31 Identifying High-Risk Markets
24:58 Structuring Debt (Post-2022)
33:17 Matt's 5-Year Vision
38:21 Advice for New Investors
41:52 Connect with Matt!
Disclaimer: This podcast is for educational purposes only and does not constitute financial, tax, or legal advice. Consult with a qualified professional before making any investment decisions.
12 Oct 2026
Making $40,000+ Profit Per Deal & Building 50+ Affordable Homes a Year | Ep. 1009
Providing affordable housing and making a profit don’t have to be mutually exclusive. One small real estate business has found a way to deliver brand-new homes in a lower price range and generate sizable margins.
Using land home packages, Chris Gavre and his partner build and sell roughly 50-60 homes per year while also addressing the affordable housing problem in his market of Greenville, South Carolina. The strategy is simple: buy and prepare an empty lot, install a manufactured house, and sell it for a sizable profit. Despite each project taking only 45-60 days to complete and selling for roughly half the median home price in his market, they net $40,000 or more per sale.
Today, Chris pulls back the curtain on land home packages and the economics behind them. He shares the mistakes that used to cost him several thousand dollars and the areas where investors can burn through their margins if they’re not careful. Our conversation also covers the finer details of the strategy, like what makes some lots more viable than others, the “sweet spot” manufactured home layout Chris prefers, and his criteria for finding markets where land home packages can scale.
Insights from today’s episode:
The “small” real estate business that flips 50-60 manufactured homes per year
How Chris nets roughly $40,000 per deal using the land home package model
The “sweet spot” manufactured homes that perform best in affordable markets
Costly mistakes to avoid when developing land home packages
Chris’s step-by-step process and timeline for completing these projects
The best ways to find land for sale (with limited time and capital)
—
Connect with Chris on Facebook
Recommended Resources:
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, click here for opportunities to invest in real estate projects alongside Kevin and his team.
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!
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.
Chapters:
00:00 Intro
01:27 Land Home Packages 101
06:42 Market Criteria & Finding Land
11:02 Appraisals & Appreciation
13:16 Real Case Studies
15:49 Painful Lessons Learned
17:31 "Sweet Spot" Manufactured Homes
23:15 Chris's Step-by-Step Process
26:37 Common Mistakes to Avoid
28:32 Connect with Chris!
Disclaimer: This podcast is for educational purposes only and does not constitute financial, tax, or legal advice. Consult with a qualified professional before making any investment decisions.
5 Oct 2026
Real Deals: We Created $15M in Value on This Commercial Property (In Year One)
Some commercial real estate investments don’t look like obvious winners on the surface. Complexity, uncertainty, and unanswered questions scare many investors away, but they can also lead to some of the best opportunities. That was certainly the case with the deal I’m about to show you: a great asset, in a great location, with more than a few hurdles along the way.
Today’s Sunrise Capital Investors case study involves a $33.2 million parking garage in Clearwater Beach, Florida. This was one of the most complex projects we’ve ever taken on, but through conservative underwriting and a figure-it-out mentality, we turned a complicated acquisition into one of the best-performing assets in our entire portfolio.
The deal required us to purchase the property in phases, coordinate with two different sellers, and navigate a nerve-wracking bidding process. Yet on the other side of these challenges was a unique asset that now generates millions in annual revenue. I’m breaking down all of the numbers, how we negotiated a triple-net lease with a corporate-level guarantee, and the value-add initiatives that increased the property’s value by over $15 million in year one.
Insights from today’s episode:
Case study: the $33 million Clearwater Beach parking garage deal
Three takeaways from this complicated commercial real estate deal
How to find off-market opportunities without cold calling or sending direct mail
The immeasurable value of networking and nurturing industry relationships
How to get a head start on value-add opportunities before you close
The complexities of purchasing one asset from two owners
—
Read the North Beach Parking Plaza Case Study
Recommended Resources:
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, click here for opportunities to invest in real estate projects alongside Kevin and his team.
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!
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.
Chapters:
00:00 Intro
02:47 Finding the Property
05:52 Why We Liked It
11:32 The Bidding Process
15:27 Triple Net Lease Negotiations
19:44 Value-Add Opportunities
22:04 Numbers on the Deal
25:48 Property Performance
28:43 3 Biggest Takeaways
Disclaimer: This podcast is for educational purposes only and does not constitute financial, tax, or legal advice. Consult with a qualified professional before making any investment decisions.
Inside a recent episode
Hidden NOI: How Design and Data Quietly Add $100K+ to Your Bottom Line
Published 12 Jan 2026 · Transcript excerpt
[…] So we want to figure out early on, is it a long -term hold? And if it's a long -term hold, that makes a difference for the kind of decisions that we're making in terms of products, materials, and also just even how we're carving out the space planning, because as you know, I'll use this for an example, packaging, mail systems, it's changed dramatically over the years, okay? So now, everyone's getting packages, large -sized packages at home, from bicycles to TVs, delivered right to the apartment. So 10 years ago, we didn't have that amount of packages coming, and in 10 more years from now, it's going to be changed from where it is. […]
Pod Engine is an independent podcast discovery and analytics service and is not affiliated with or endorsed by this podcast. Artwork and show content belong to their owners. Full legal notice.
Explore this show Podcast research with Pod Engine
