Why This Founder Built Hotels for People Who’d Rather Be Outside

What if the best hotels weren’t designed to keep you inside—but to get you out into the world? On this episode of Suite Success, host Katie Cline sits down with Mike Weiss, co-founder and co-CEO of Trailborn Hotels and Resorts, to unpack how he’s building a boutique hospitality brand around nature, experience, and intentional growth. Mike’s path to hospitality wasn’t linear. From investment banking and real estate private equity to early-stage startups and product leadership, his career ultimately converged on one clear insight: travelers don’t just want beautiful rooms—they want meaningful experiences rooted in place. Mike shares how Trailborn identifies iconic outdoor destinations, repositions existing assets near national parks, beach towns, and mountain towns, and designs hotels that act as a launchpad for exploration—not a retreat from it. Together, Katie and Mike discuss what takes to build a modern hospitality brand: balancing growth with quality, real estate returns with guest experience, and ambition with restraint. They also dig into co-founder dynamics, the realities of scaling in remote markets, and why clarity about your customer is one of the most powerful competitive advantages you can have. Connect with Mike: Mike's LinkedIn: https://www.linkedin.com/in/mikedweiss/ Trailborn Hotels & Resorts Website: https://www.trailborn.com/ Links: Apple Podcasts - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Link⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Spotify - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Link⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Suite Success Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Link⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Connect with Katie⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠