In this episode of the Collective Genius Podcast, I sit down with real estate investor Casey Gregersen, who shares his incredible journey from a Wyoming kid dreaming of being a sports announcer to scaling a successful real estate investment business across multiple states. We unpack how Casey transitioned from oil and gas engineering into full-time real estate, leveraging his unique advantages in overlooked markets like Wyoming and surrounding states.

Casey opens up about the pivotal moments that shaped his investing path—from buying his first rental in college to strategically using his W-2 income to scale, and how he turned challenges into stepping stones for building a thriving multifamily portfolio. We also explore Casey’s approach to building teams remotely, raising capital, and applying corporate processes to his real estate business. If you’re looking to learn how to operate successfully in niche markets or take the leap from single-family to multifamily, this episode is a must-listen!

Timeline Highlights

[0:00] - Introduction

[1:30] - Casey talks about moving from Wyoming to Houston and why he focuses on investing in Wyoming, Montana, and surrounding states.

[4:00] - Casey explains how low competition in Wyoming allowed his direct-to-seller strategy to thrive with virtually no marketing competition.

[8:15] - Casey shares his childhood dream of becoming a sports announcer and how his passion shifted from communications to math and chemistry.

[15:00] - Casey discusses how buying his first college rental and reading Rich Dad, Poor Dad planted the seed for a real estate career.

[20:00] - We hear how Casey’s oilfield schedule—two weeks on, two weeks off—let him learn about real estate and flip houses on his time off.

[25:00] - Casey recounts tough lessons from attempting high-end flips in the Dallas area, contractor challenges, and almost leaving real estate altogether.

[26:00] - Casey talks about moving back to Houston, regrouping after setbacks, and doubling down on his Wyoming portfolio.

[29:00] - How layoffs and instability in the oil and gas industry during COVID-19 accelerated Casey’s push toward full-time real estate investing.

[32:00] - Casey shares how building systems, standard operating procedures (SOPs), and hiring virtual assistants gave him leverage to scale remotely.

[36:00] - We explore Casey’s methods for finding great local contractors and agents in markets where he doesn’t live.

[41:00] - Casey details how he transitioned from small multifamily to taking down his first 14-unit, then a 63-unit multifamily deal, and the mindset shifts that required.

[44:00] - Casey explains how he started raising capital, why he documented his journey to build investor trust, and how that led to a successful $1.7 million raise for a 45-unit deal.

[47:00] - We wrap up with a discussion about the importance of building strong banking relationships, knowing what local banks want to lend on, and leveraging your W-2 to stay bankable until the right time to go full-time.

1. Niche markets can be goldmines – Low competition in places like Wyoming can create massive opportunities for investors willing to do the work others won’t.

2. Leverage your W-2 income – Casey’s corporate job made him bankable, helping him scale faster and secure financing.

3. Corporate skills translate – Systems, SOPs, and processes from Casey’s time at Shell gave him an edge in scaling his real estate business.

4. Relationships matter – Building strong connections with local agents, contractors, and banks is critical, especially when investing remotely.

5. Document your wins – Sharing real success stories with potential investors builds trust and credibility when it comes time to raise capital.

Links & Resources

Collective Genius Podcast Website: https://go.thecollectivegenius.com/podcast/

Learn more about Casey Gregersen’s investing strategies (consider adding Casey’s website or LinkedIn if applicable).

Thanks so much for tuning into this episode of the Collective Genius Podcast! If you enjoyed Casey’s inspiring journey from oilfields to multifamily success, please take a moment to rate, follow, and leave a review on your favorite podcast platform—and don’t forget to share this episode with a fellow investor who needs a little push to chase their dreams!