327: How Casey Turned One Rental Into 250 Deals episode artwork

EPISODE · Apr 9, 2025 · 39 MIN

327: How Casey Turned One Rental Into 250 Deals

from The DealMachine Real Estate Investing Podcast · host Casey Gregersen, David Lecko

Are you finding that solely focusing on wholesale assignments limits your ability to capture long-term wealth and leaves you reliant on constantly finding new buyers? In this episode, we speak with Casey Gregersen, who started with his first off-market deal in 2010 and has built a vertically integrated real estate business. Casey will share how he evolved beyond just wholesaling, incorporating in-house construction and property management for his rental portfolio, aiming to complete 100 deals this year across various strategies. Learn how you can expand beyond the constraints of strictly wholesaling by understanding the benefits of buy-and-hold, fix and flip, and even raising capital to build a more resilient and profitable business.Here are three more impressive things about Casey Gregersen:Casey's real estate journey began with house hacking his first off-market deal in 2010, immediately generating cash flow by renting out rooms.Despite starting in real estate early, Casey continued to work a full-time W2 job at Shell for several years, strategically using his income and time off to learn and invest further.Casey made a significant life decision to leave his full-time job at Shell after realizing he was missing important family moments, demonstrating his commitment to aligning his work and personal priorities after building a stable real estate business. KEY TALKING POINTS:0:00 - An Overview Of Casey Gregersen’s Business1:39 - When Casey Did His First Off-Market Deal3:49 - His Next Deals After That7:04 - The Mindset That Allowed Him To Rent Out His First Property9:20 - What Casey Would Say To People Who Think Interest Rates Are Too High13:12 - Is It Too Late To Invest In Real Estate?14:55 - Casey’s Lowest Lows In Business17:25 - His High Points In Business21:06 - What He’d Be Doing If He Never Got Into Real Estate22:20 - What He’s Looking Forward To Most In 202523:25 - The Data That Casey Needs The Most28:18 - The Last Topic He Spoke About At Collective Genius That Made Him Proud29:26 - The Mindset That Led To Casey’s Success31:36 - Tax Cheat Codes & The Entrepreneur Mindset39:02 - Outro LINKS:Instagram: Casey Gregersenhttps://www.instagram.com/caseygregersen Website: Casey Gregersenhttps://caseygregersen.com/ Instagram: David Leckohttps://www.instagram.com/dlecko Website: DealMachinehttps://www.dealmachine.com/pod Instagram: Ryan Haywoodhttps://www.instagram.com/heritage_home_investments Website: Heritage Home Investmentshttps://www.heritagehomeinvestments.com/

Casey reveals how keeping one rental changed everything—leading to 250+ deals, a creative financing strategy, and the freedom to walk away from his job.

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327: How Casey Turned One Rental Into 250 Deals

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This episode is 39 minutes long.

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This episode was published on April 9, 2025.

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Are you finding that solely focusing on wholesale assignments limits your ability to capture long-term wealth and leaves you reliant on constantly finding new buyers? In this episode, we speak with Casey Gregersen, who started with his first...

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