Real Estate Underground

From Oil Fields to Real Estate Empires with Casey Gregersen

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Casey Gregersen worked twelve years as a petroleum engineer at Shell. The job had an unusual rhythm: two weeks on a drilling rig, two weeks completely off with zero work responsibility. He used the off weeks to start buying houses. In October 2022, with three companies running, he walked away from Shell.

Today Casey runs Bighorn Capital Fund, Wile Homes, and Gregersen Properties. He invests primarily in Wyoming, a market where his only real competition is the lack of contractors to keep up with demand. That contractor shortage was the central problem he had to solve to scale.

What landed in this conversation:

  1. The VA build during COVID layoffs. Shell laid off 40 percent of Casey's team in 2020. Instead of waiting to see if his number got called, he sat down and read The 4-Hour Work Week, then recorded himself doing every property management task he was already running from Houston. Wrote it all into SOPs. Hired and trained a virtual assistant. The VA owned the SOPs from that day. That was the unlock that let the side hustle scale.
  2. The local bank shortcut. Early on, instead of working with big mortgage brokers, Casey walked into a small local bank in the Wyoming town he was investing in and did a deal. The relationship compounded across dozens of properties. Most new investors miss this because they assume the broker network is the only path.
  3. The in-house contractor model. Wyoming does not have a deep GC bench. Casey solved it by hiring four to five 1099 crews directly. When a deal hits his pipeline, he is talking to the guy who will actually do the work, and that guy controls the schedule. The timeline gets predictable. The carry costs drop. The investor pitch becomes "here is our budget and here is our timeline, and we know we can hit it" because the labor is not a third party balancing five other clients.
  4. The two-exit rule. Casey scaled up to $500,000 to $700,000 fix-and-flips in the TCU area with a new GC and project manager. Properties stopped selling. He had to drop the list price by $10,000 a week until they cleared, on the advice of his hard money lender. The lesson, in his words: never run a flip where your only exit is selling at ARV. Always have a refinance-and-rent fallback. In Wyoming his $150,000-buy / $50,000-rehab / $300,000-sell deals could always pivot to a rental that covered the debt. Every single deal has a curveball.

    5. Book Casey keeps coming back to: Capital Gaines by Chip Gaines, for the "win-win either way" framing.

    Reach Casey at @CaseyGregersen on YouTube, Instagram, and LinkedIn, or text him directly at 307-317-2494.

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    Real Estate UndergroundBy Ed Mathews
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