The Hotel Investor Playbook He Managed $320M for a Family Office - Then Walked Away to Build His Own Empire | Reilly Brennan E32
May 20, 2025
Reilly Brennan, founder of the Trailside Hotel in Duluth, previously scaled a family office's real estate portfolio from $3M to $320M. He shares his bold transition to boutique hospitality, discussing how he acquired two hotels and the creative seller financing used. Reilly highlights his decision-making strategies in fast-paced deals, the emotional journey of entrepreneurship, and the significance of design in crafting guest experiences. Listeners gain insights into the hidden potential of small deals and the fulfillment that comes from pursuing one's vision.
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Leaving Stability To Build Your Own Vision
- Reilly left a high-growth family office despite equity because he wanted to create his own vision.
- He describes entrepreneurship as exhilarating and humbling, and says he can't go back to W2 work.
Finding Deals Through Tax Records And Rapport
- Reilly found his first hotel by researching tax records and owner age to target seller financing opportunities.
- He became guests, built rapport, and negotiated seller-financed terms with the owners.
Win By Being The First Offer
- Reilly acted immediately on a LoopNet alert for a 22-unit property and met the seller within minutes with an LOI and earnest money.
- His speed convinced the owner to stop other calls and accept their contract, enabling a fast close.