Real Estate Investing for Cash Flow with Kevin Bupp

Kevin Bupp
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Sep 1, 2025 • 41min

#941 Scaling Smarter: Spencer Gray on Building Multifamily Success in the Midwest

Spencer Gray is the founder and President of Gray Capital, an investment firm based in Indianapolis that specializes in value-add multifamily properties in select Mid-western markets. Spencer leads all strategic initiatives at the firm, including investment strategy, capital raising, and property operations. Since founding Gray Capital with his wife Alex, Spencer has been involved in over $2.5 billion in real estate transactions and currently controls over $750M in multifamily real estate. Connect with Spencer: https://www.graycapitalllc.com/  Highlights: 5:00 – Spencer's entrepreneurial family history 7:00 – Early challenges 12:00 – Why Gray Capital focuses on Indianapolis and the Midwest 18:00 – In-house property management company for more control 24:00 – Technology, centralization, and better-trained leasing agents 32:00 – Buying a fractured condo deal mid-pandemic Quote: “You can find the best deal in the best market and raise all the money you need, but if you don’t execute on operations, you can still lose money. Operations is where the rubber meets the road.”   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.
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Aug 29, 2025 • 38min

FBF #940: Create Financial Independence Through Your Investments

Today's Flash Back Friday episode is from #558 that originally aired on Feb. 27, 2023. Chris Larsen is the founder and Principal of Next-Level Income. Since “retiring” after 18 years in the medical device industry he dedicates his time to helping others become financially independent through education and investment opportunities. Chris has been investing in and managing real estate for over 20 years. While completing his degree in Biomechanical Engineering and M.B.A. in Finance at Virginia Tech, he bought his first single-family rental at age 21. Chris expanded into development, private-lending, buying distressed debt as well as commercial office, and ultimately syndicating commercial properties. He began syndicating deals in 2016 and has been actively involved in over $1B of real estate acquisitions. Quote:   I hit this moment where you’ve done something, you pick your head up and you realize there’s more to life than this. This isn’t what it’s really all about.  Highlights:   06:02: Chris’s first property and how it shaped the rest of his career 09:05: Growing on your investment journey while working a W2 job 13:20: Making the switch from single family to commercial investments 15:05: How Chris decided to switch to syndication as a path to financial independence 17:10: The assets Chris is currently investing in 19:42: Value add opportunities in newer Class A apartment complexes 21:10: Navigating current market volatility and what that looks like in the long term 24:10: Integrating infinite banking into your life Connect with Chris: https://nextlevelincome.com/ 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.
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Aug 27, 2025 • 1h 12min

MHP #939: A Step-by-Step Guide to Successful Mobile Home Park Management

Today's episode is form Mobile Home Park #17 that originally aired on Aug. 2 2017. Charles and I will be discussing how to successfully manage your mobile home park. Over the last few weeks, we’ve personally been flooded with emails from people who asked questions relating to this topic. Instead of responding to each individually, we decided that it would provide much more value if we take each of your questions about the management and make a show on it. This is broken down into four basic sections. These will be: The bare minimum of what a manager needs to be able to do Things that a manager can do to potentially get paid more money Things a manager should not be doing How to find a manager for your park We’ll cover everything from A to Z as it relates to running a successful mobile home park.   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.
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Aug 25, 2025 • 51min

#938 From Corporate Layoffs to Flipping Dirt: How to Build Freedom Through Land Investing

Land Investment experts, Mike and Ligia Deaton are a husband-and-wife team who transitioned from the corporate rat race to full-time land investors and educators. After being laid off on the same day from high-pressure corporate jobs, they turned what could have been a major set back into an entrepreneurial spring board, launching Flipping Dirt, a company focused on buying and selling raw, vacant land for profit. Their mission is to help others achieve time and financial freedom by building a simple, scalable land flipping business. Connect with Mike & Ligia: https://flippingdirt.us/  Highlights: 5:00 – Mike & Ligia lost their corporate jobs on the same day 9:00 – Why land flipping stood out, low entry costs, outsized returns 13:00 – Buying below market value, reselling for cash or seller financing 20:00 – Direct mail, texting, AI 24:00 – Simple due diligence process 38:00 – Owner financing and managing defaults 46:00 – Lessons learned: start bigger, buy more early   Quote: “What could’ve been a punch in the gut, a double layoff became our springboard. We chose not to go back to the rat race, but to build freedom through land.” 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.
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Aug 22, 2025 • 47min

FBF #937: Transitioning From a Full-Time Employee to a Full-Time Real Estate Investor

Today's Flashback Friday episode is form #280 that originally aired on July 20, 2020. Spencer’s investment firm, Madison Investing, has co-sponsored deals totaling more than 5000 units equaling more than $600M. As a former technology leader, Spencer built a 13 year track record of growing high-performing teams across five companies - three of them, "unicorns" - valued at more than $1B. In November 2019, Spencer “retired” from his lucrative technology career - leaving behind the $4B loan origination teams he built at LendingHome, which funds an average of 600 fix/flip transactions per month. Now, he is focused on spending time with loved ones and growing Madison Investing by helping passive investors achieve their goals." 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.
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Aug 20, 2025 • 7min

MHP #936: Choose to Invest Locally Over Logically

Today's episode is from Mobile Home Park #16 that originally aired on July 28, 2016. Charles and I will discuss mistake number 8 from our popular eBook, “The 21 Biggest Mistakes Investors Make When purchasing their First Mobile Home Park…and how to avoid them.” One thing we see often is that many investors will choose to look for parks locally for the sole purpose of being near the park. There is nothing wrong with being close to your park, but you definitely don’t need to be. If you find that you live in a market where CAP rates are insanely low or in a market that is going through tough times, you would be much wiser to invest outside of your immediate area. The business model and management style we teach is effective whether you live across the street from your park or across the country. Don’t put yourself in the position of buying a bad investment just for the sake of being close to it. Proximity does not correlate to success in this business. 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.
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Aug 18, 2025 • 30min

#935 Multifamily in Transition: Strategies for Today’s Market with Gary Lipsky

Gary Lipsky is the president of Break of Day Capital, an investment firm that specializes in multi-family real estate in Arizona. Gary brings a 20+ year track record in the real estate space and has completed more than $300M of transactions over his career. Gary is also the host of the Real Estate Investor Podcast, where he interviews industry experts to provide broad range education to investors. He is also the best-selling author of Best in Class, founder of the Asset Management Summit, and a guest speaker featured at many prominent conferences. Connect with Gary: breakofdaycapital.com  Highlights: 02:55 – How Gary's entrepreneurial roots and first house hack in Los Angeles planted the seed for a multifamily career. 04:10 – Current challenges in Arizona 06:00 – Why today’s market offers opportunity 09:50 – Outsourcing property management 12:45 – Experimenting with AI for investor communications, research, marketing 19:00 – The capital raising challenge 21:10 – Advice to LPs: focus on the operator’s track record and discipline   Quote: “If a deal sounds too good to be true, it probably is. Don’t chase IRR or bonus depreciation—chase a good operator, and everything else will work out.”   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.
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Aug 15, 2025 • 41min

FBF #934: Insights with Lee Fjord on Property Management and Powerful Partnerships

Today's Flash Back Friday episode is from #747 that originally aired on May 27, 2024. Lee got his start in real estate in 2012 building a property management department of a residential brokerage from 20 doors to 220 doors in 4 years. After being inspired by his clients’ successes, he decided to start investing in 2016. Relocating to St. Louis in order to pursue investing in 2017, Lee began with a duplex and continued to purchase smaller properties until he found “The Power Of Partnerships” by partnering withan ex-NFL player from CA and with their combined efforts, were able to close a 38 unit apartment complex Joint Venture in Lee's backyard of St.Louis, MO in October of 2019. Fast forward to today and Lee has grown his portfolio to 1000 units with no end in sight! Connect with Lee: greenforestcapital.com  Highlights: 5:51 - From Property Management to Big Deal (Lee's game plan) 10:51 - Lee's Training on Getting Owners to Commit 16:02 - Finding The Right Partners 26:08 - Why You Must Be Involved with Property Management 31:44 - All About Lee's Team/Organization Quote: " You have to be on site, you have to have your fingers in the pie, you can't just leave it to the management company to execute..."   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.
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Aug 13, 2025 • 36min

MHP #933: Dominate the "For Rent & For Sale" Real Estate Categories in Craigslist & Create an Endless Supply of Leads

Today's episode is from Mobile Home Park that originally aired on Oct. 4, 2016. Charles and Kevin discuss how to add rocket fuel to your advertising efforts and absolutely dominate craigslist. Their strategy will show you how to hire and train a Virtual Assistant to post continuous ads for your available homes and lots, thus creating an endless supply of prospective residents. This is a must for any mobile home park operator who has either available homes or lots within their community. 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.
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Aug 11, 2025 • 33min

#932 Invest Like a Billionaire: Navigating Alternative Assets with Bob Fraser

Bob Fraser is the co-founder and CEO of Aspen Funds, an investment firm offering alternative investments ranging from private equity, mortgage notes, oil & gas, and industrial. Bob is responsible for financial management, portfolio modeling, as well as systems and processes. Additionally, Bob is the co-host of the Invest Like a Billionaire podcast where he dives into the world of alternative investments and speaks with successful investors. On his show, he also discusses economic trends, including mega trends such as inflation, energy prices and deglobalization. His goal is simple, it's to empower others looking to explore less volatile investment opportunities, improving their portfolio’s performance, and enabling them to become more financially secure.   Aspen Funds: aspenfunds.us – for information on Bob's investment firm. Book link: thebillionairebook.org – to preorder Invest Like a Billionaire and access bonus materials.   02:55 – From dot-com success and loss to discovering the control and stability of private alternative investments. 05:00 – Buying distressed debt after the 2008 crash 09:15 – Why oil and gas is a contrarian play today 14:50 – Red flags in oil and gas investing and the importance of institutional-grade operators over speculative drilling. 17:00 – Aspen’s focus on private credit and industrial real estate 23:55 – The book Invest Like a Billionaire—how billionaires diversify into private alts, lower risk, and achieve higher returns than traditional portfolios.   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.

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