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Artwork for Real Estate Investing for Cash Flow

Real Estate Investing for Cash Flow with Kevin Bupp

Kevin Bupp
Mobile Home Parks
Real Estate Investment
Passive Income
Real Estate Investing
Mobile Home Park Investing
Commercial Real Estate
Cash Flow
Real Estate
Property Management
Investment Strategies
Affordable Housing
Real Estate Development
Interest Rates
Owner Financing
Financial Independence
Syndication
Industrial Real Estate
Investment Strategy
Short-Term Rentals
1031 Exchange

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 m... more

PublishesWeeklyEpisodes1012Founded13 years ago
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Artwork for Real Estate Investing for Cash Flow

Latest Episodes

After more than 50 years in commercial real estate, Bill Cummings has built an 11-million-square-foot portfolio spanning 12 communities around Greater Boston. But he did so by ignoring many of the conventional rules of real estate investing.

When hi... more

Early on, most real estate investors are chasing the same thing: more. More properties. More units. More cash flow. But eventually, “more” becomes a trap.

Every acquisition brings new challenges and risks. At some point, the smartest move isn’t buyi... more

Tax liens are often pitched as a passive way to earn double-digit returns from investments that are backed by real estate.

This is only half true.

While these investments average 13%-18% annual returns, they may actually be one of the least passive... more

America’s affordable housing crisis is well documented. We’re currently short millions of homes, and the number doesn’t seem to be going down.

The problem is more complicated, but more solvable, than it appears. Factory-built housing—such as manufac... more

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Recent Guests

Bill Cummings
Billionaire founder of Cummings Properties; author
Cummings Properties; The Cummings Foundation
Episode: 99% Passed on These Commercial Properties. They Made Him a Fortune.
Chris Lopez
Co-founder of PassivePockets, real estate investor
PassivePockets
Episode: He Tripled His Cash Flow by Doing What Most Buy-and-Hold Investors Won’t | Ep. 1003
Stephen Morel
Real estate investor, attorney, title professional, founder of JurisDeed
JurisDeed
Episode: How to Earn a 13%-18% Average Annual Return in 2026 (Tax Lien Investing 101) | Ep. 1002
Galiano Tiramani
Co-founder of Boxabl
Boxabl
Episode: The State of Affordable Housing in 2026 w/ BOXABL CEO Galiano Tiramani | Ep. 1001
Mike Hart
Chief Financial Officer at Sunrise Capital Investors
Sunrise Capital Investors
Episode: The Keys to a Tax-Efficient Real Estate Exit (1031 Exchanges, DSTs, & More) | Ep. 1000
John McNellis
Founder of McNellis Partners; author of Making It in Real Estate
McNellis Partners
Episode: 50 Years and 100+ Real Estate Development Deals: What I’ve Learned | Ep 999
Danielle Ash
Partner at Adler & Stachenfeld, co-chair of ground lease practice
Adler & Stachenfeld
Episode: How to Lock in 99 Years of Cash Flow (Today) with Commercial Ground Leases | Ep. 997
Jordan Blanchard
USDA lending expert, focuses on USDA 1RD programs
X-Caliber Rural Capital
Episode: How to Fund Your Next Commercial Real Estate Deal with USDA Financing | Ep. 996
Hannah Hammond
Founder and CEO of HB Capital
HB Capital
Episode: She Oversees $150M Acquisitions: Here’s What “Smart” Operators Are Doing Today w/Hannah Hammond

Host

Kevin Bupp
Host of the show

Reviews

4.8 out of 5 stars from 730 ratings
  • A Must-Listen

    Every episode feels like a mini masterclass. The conversations are thoughtful, clear, and packed with value.

    Apple Podcasts
    5
    Jessica Guison
    Philippines10 months ago
  • Well worth a listen!

    Loving this podcast, Kevin is a great host!

    Apple Podcasts
    5
    Poppy@davedubeau
    United Kingdoma year ago
  • Great value

    Amazing value, thank you for taking the time to share your experience Kevin and Charles!

    Apple Podcasts
    5
    Eric_S_C
    United States2 years ago
  • Kevin is an Expert in Mining Value

    Kevin is the go-to source for cash flow investing.

    He covers a wide range of topics, truly scales CRE assets himself, and knows how to bring out the best in the people he interviews.

    FOLLOW THIS SHOW!! 🏦

    Apple Podcasts
    5
    DakMalone
    United States3 years ago
  • Left a 5-star review!

    Great show! Kevin is well spoken and easy to follow through tough concepts. Episodes are packed with great info.

    Apple Podcasts
    5
    JustinMoy93
    Philippines3 years ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Listeners view the show as a reliable source for CRE insights and strategies.
Listeners praise actionable, masterclass-like episodes with clear, practical takeaways.
The host is consistently seen as expert and easy to follow.
Diversity of guests provides broad CRE perspectives and real-world lessons.
Episodes are valued for deep dives into sophisticated financing and deal-making.

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Talking Points

Recent interactions between the hosts and their guests.

99% Passed on These Commercial Properties. They Made Him a Fortune.
Q: Can you walk us through the United Shoe Machinery/Beverly deal and what made it possible to turn a seemingly poor asset into a fortune?
The property looked like a disaster with environmental and structural problems, but the size, central city location, and the ability to clean up and repurpose the land created enormous upside; the team moved quickly, did not over-leverage, and built a powerful, long-term plan around redevelopment and leasing.
He Tripled His Cash Flow by Doing What Most Buy-and-Hold Investors Won’t | Ep. 1003
Q: What should LPs ask about the sponsor's capital stack and debt strategy?
Inquire about loan-to-value, debt terms, extensions, contingency plans, and whether the sponsor uses conservative leverage that can sustain distributions during market stress.
He Tripled His Cash Flow by Doing What Most Buy-and-Hold Investors Won’t | Ep. 1003
Q: How should an investor think about diversification after accumulating wealth?
Balance between real estate and stocks, starting with familiar asset classes, layering in debt investments, and limiting exposure to any single sponsor to maintain diversification and manage risk.
He Tripled His Cash Flow by Doing What Most Buy-and-Hold Investors Won’t | Ep. 1003
Q: What red flags do you look for when vetting a sponsor for a passive investment?
Key man risk, track record with full-cycle projects, risk mitigation practices, conservative debt terms, transparent communication, and independent verification from peers and LP networks.
He Tripled His Cash Flow by Doing What Most Buy-and-Hold Investors Won’t | Ep. 1003
Q: Run me through the decision-making process for recapping or reinvesting when cash flow is tight.
The guests explain evaluating base case numbers, the market cycle, and the goal alignment against leverage and asset health, using tools like cash flow analysis, refinancing options, and the feasibility of a 1031 exchange to optimize returns and risk.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

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Frequently Asked Questions About Real Estate Investing for Cash Flow

What is Real Estate Investing for Cash Flow about and what kind of topics does it cover?

A practical, expert-driven show for serious commercial real estate investors seeking to build long-term cash flow and wealth. Episodes frequently tackle tax-efficient exits, sophisticated financing structures, and capital-raising strategies, from 1031 exchanges and DSTs to ground leases, USDA financing, and private lending. The conversations blend real-world deal stories with actionable frameworks, underwriting insights, and lessons from seasoned operators, making it valuable for operators, developers, and sponsors aiming to elevate their CRE game. A notable strength is the depth and breadth of guests, spanning CFOs, developers, lenders, and lawyers, which helps listeners understand diverse perspectives across asset classes and capital stac... more

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Which podcasts are similar to Real Estate Investing for Cash Flow?

These podcasts share a similar audience with Real Estate Investing for Cash Flow:

1. Lifetime Cash Flow Through Real Estate Investing
2. The Best Ever CRE Show
3. Rental Income Podcast With Dan Lane
4. Ken McElroy Show
5. Real Wealth Show: Real Estate Investing Podcast

How many episodes of Real Estate Investing for Cash Flow are there?

Real Estate Investing for Cash Flow launched 13 years ago and published 1012 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on Real Estate Investing for Cash Flow?

Recent guests on Real Estate Investing for Cash Flow include:

1. Bill Cummings
2. Chris Lopez
3. Stephen Morel
4. Galiano Tiramani
5. Mike Hart
6. John McNellis
7. Danielle Ash
8. Jordan Blanchard

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