Reilly Brennan

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.