After helping scale a family office real estate portfolio from $3 million to over $320 million, Reilly Brennan walked away from the comfort of a W-2 job to carve his own path in boutique hospitality.

In this episode, we sit down with Reilly to unpack how he sourced and acquired two independent hotels in Duluth, Minnesota, one through creative seller financing, the other straight off LoopNet. We break down his underwriting process, deal structure, construction strategy, and how he’s building a brand that reflects his values, not someone else’s investment thesis.

You’ll also hear:

Why Reilly left the multifamily world for experiential hospitality
How he underwrote a $700K deal in real time, then moved fast to close it
His approach to FF&E, design, and building a team from scratch
What it actually feels like to go all-in on your own vision
The hidden value of small deals when you’re playing a long game

Whether you’re just getting started or thinking about scaling, this episode is full of honest insight about the hard work and fulfillment that come with betting on yourself.

Connect with Reilly:

Website: https://www.thetrailsidehotel.com

Instagram: https://www.instagram.com/the.brennan.buzz/

LinkedIn: https://www.linkedin.com/in/reilly-brennan-258968172/

Connect with Mike and Nate:

Los Angeles Investment Info: malama-capital.com/invest

Instagram: @the_hotel_investor_playbook

He Managed $320M for a Family Office - Then Walked Away to Build His Own Empire | Reilly Brennan E32