Real Estate Investing for Cash Flow with Kevin Bupp

Kevin Bupp
undefined
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.
undefined
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.
undefined
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.
undefined
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.
undefined
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.
undefined
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.
undefined
Aug 8, 2025 • 42min

FBF #931: Scale Up Big in Real Estate & Multi Family Sectors

Today's Flashback Friday episode is from #722 thats originally aired on March 25, 2024. Darin Davis is an industry leader, real estate entrepreneur, and founder of Club Capital and brings over two decades of industry leadership and more than $1bn of sponsored real estate projects. He excels in navigating market shifts and guiding investors to exceptional returns, even in times of uncertainty like we’re facing today. Aside from his real estate endeavors and in partnership with his two children, he launched The Never Quit Initiative, which is a 501(c)(3) non-profit organization. The Never Quit Initiatives mission is to broadly educate young adults on the power of passive cash flow for income and prepare financially for a potential crisis in healthcare costs. Highlights: 8:45 - Making Deals w/ H.U.D. 13:53 - Multi-Family Sector Strengths 21:26 - How To Vet Sponsors 23:31 - Multi-Family Sector Weaknesses 33:38 - Dividing A Clubhouse / Amenities Quote: "It's good that I didn't know what I was doing - If I did, I would have panicked and done nothing." Connect with Darin: clubcapital.co/investing    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.
undefined
Aug 6, 2025 • 35min

MHP #930: What to Do When Purchasing a Park with Inferior On-Site Management & Maintenance Teams

Today's episode is from Mobile Home Park #27 that origianlly aired on Sep. 27 2016. Our experience in a park we own in Raeford, NC. We recently acquired this park and quickly realized that both the on-site management and maintenance staff needed to be replaced ASAP! We discuss how we quickly identified the challenges associated with their poor performance and how we handled the transition with a completely new management team. This is a common scenario you will experience when purchasing turnaround or distressed mobile home parks and so we thought you might learn from our personal experience.    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.
undefined
Aug 4, 2025 • 37min

#929 Land Rich: Unlocking Massive Returns with Raw Dirt and Creative Financing

Dan Haberhosk is the founder and CEO of Front Range Land and Mason McDonald Founder of Colorado Land Acquisition services and both of which are investment firms that focus on raw land investments. This runs the gamut of in fill plots of land in suburban areas, rural tracts, ranches, land development and much more. While Dan and Mason run their own independent investment firms, they co-own a lending company that specializes in lending on raw land. For that, I thought it would be fun to have them both join the show. Dan Haberkost https://danbercot.com Instagram: @danbercot Mason McDonald Instagram: @masonrmcdonald 🎙️ The Big Picture Blueprint – Available on all major platforms.   Highlights: 3:00 - From Corporate Climb to Land Hustle 8:00 - Why Land Is the Wild West of Real Estate 17:00 - Seller Financing as a Wealth Machine 31:00 - The Goldmine Gamble in Alaska   Quote: “The beauty of land is that, literally from the ground up, you're controlling the asset, there are layers of value each step of the way.”   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.
undefined
Aug 1, 2025 • 21min

FBF #928: Transforming Shipping Containers into Homes

Today's Flash Back Friday episode is form #705 that originally aired on Feb 12 2024. Sean is owner of Bold Estimation, one of the largest out sourced construction estimation companies in the United States with nearly 100 employees. In addition to his estimation firm, Sean also specializes in building affordable housing out of shipping containers. His own personal residence is a 5,000 sq ft home that utilizes six shipping containers as the basis of the design. With this unique construction method, he’s been able to build affordable housing communities with costs as low as $75/sq ft all-in. Connect with Sean: https://www.boldestimation.com/  Highlights: 4:51 - Financing 8:05 - Challenges & Layout 11:45 - Other uses for Shipping Containers & Cost   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.

The AI-powered Podcast Player

Save insights by tapping your headphones, chat with episodes, discover the best highlights - and more!
App store bannerPlay store banner
Get the app