If you’ve ever felt torn between your passions, Ryan Montgomery is here to blow up the idea that you have to pick just one. He’s a 100-mile ultra runner. He’s getting his MBA. He leads queer running retreats. He’s a strategist. A community-builder. A multi-hyphenate who refuses the neat little boxes the world offers.

And somehow? It all works.

Ryan’s story doesn’t start on a podium — it starts in the woods. A middle school camping trip. A kid who decided to run laps while everyone else roasted marshmallows. That instinct to move toward what feels impossible has carried him through 50+ ultras and nearly 20 hundred-milers.

Every race isn’t just a test — it’s a laboratory. A place to crack open the mind, explore the edges, and figure out what happens when you stop avoiding discomfort and start expecting it.

Ryan doesn’t hope things go smoothly. He welcomes the stomach issues, the rolled ankles, the “I might crumble” moments. And that mindset spills into everything — school, work, relationships. If he knows hard moments will come, he’s free to meet them with curiosity instead of fear.

It’s resilience, but more intentional, more tactical, more human.

Ryan shares his biggest lesson in injury: you can’t just manage pain; you have to understand it. Treating symptoms is easy. Investigating the real problem is hard.
But hard is kind of Ryan’s thing.

He’s not just running; he’s thinking strategically about the entire industry. Sponsorship models. Go-to-market gaps. Missed opportunities. Ryan brings the business brain brands should want, and he’s honest about why many still don’t know how to use athletes like him. This is where Janji shines for him: small enough to collaborate deeply, aligned enough to feel like home.

What started as a “What if this never works?” idea became a wildly joyful queer running retreat that sells out year after year. It’s sweaty, silly, affirming, and safe in a way the outdoor world often isn’t.

People arrive as strangers. They leave as something else entirely.

Ryan opens up about identity, alignment, discomfort, injury, ambition, and what it takes to build a life that feels like you, not just the version that fits everyone else’s expectations.

If you’re multi-passionate, craving community, navigating a big transition, or just trying to find your own “corner of the mind,” this episode is a must.

Listen to this episode on your long runs this weekend 👇

Jon is a runner, cyclist, and podcast host from Boston, MA, who now lives in Boulder, CO. For The Long Run is aimed at exploring the why behind what keeps runners running long, strong, and motivated.

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