327: How Casey Turned One Rental Into 250 Deals

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 Business 1:39 - When Casey Did His First Off-Market Deal 3:49 - His Next Deals After That 7:04 - The Mindset That Allowed Him To Rent Out His First Property 9:20 - What Casey Would Say To People Who Think Interest Rates Are Too High 13:12 - Is It Too Late To Invest In Real Estate? 14:55 - Casey’s Lowest Lows In Business 17:25 - His High Points In Business 21:06 - What He’d Be Doing If He Never Got Into Real Estate 22:20 - What He’s Looking Forward To Most In 2025 23:25 - The Data That Casey Needs The Most 28:18 - The Last Topic He Spoke About At Collective Genius That Made Him Proud 29:26 - The Mindset That Led To Casey’s Success 31:36 - Tax Cheat Codes & The Entrepreneur Mindset 39:02 - Outro LINKS: Instagram: Casey Gregersen https://www.instagram.com/caseygregersen Website: Casey Gregersen https://caseygregersen.com/ Instagram: David Lecko https://www.instagram.com/dlecko Website: DealMachine https://www.dealmachine.com/pod Instagram: Ryan Haywood https://www.instagram.com/heritage_home_investments Website: Heritage Home Investments https://www.heritagehomeinvestments.com/