The DealMachine Real Estate Investing Podcast

327: How Casey Turned One Rental Into 250 Deals

Episode Summary

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.

Episode Notes

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/