Jon is the founder of Getaway (now Postcard Cabins) and was CEO through its acquisition by Marriott in December 2024. Getaway grew from Jon’s lifelong appreciation for the great outdoors, having grown up in a cabin in rural northern Minnesota. Under his leadership, the company raised $300m+, grew to 500+ team members, and amassed millions of social media followers.

Jon is the author of Getting Away: 75 Everyday Practices for Finding Balance in Our Always-On World (Penguin), was host of The Getaway Podcast, and appeared on Shark Tank. He is also the co-designer of architecture featured in Dwell and on HBO.

Jon was included on Crain’s inaugural LGBTQ Leaders’ Executives list and is also a member of the Advisory Board at the Ali Forney Center. He earned his AB and MBA from Harvard University, where he is currently an Entrepreneur-in-Residence.

What do you appreciate about being a collaborator at Newcastle?

I have loved my companies, but working with Newcastle gives me exposure to the rest of the world. Through Newcastle, I not only get to peek under the hood of lots of interesting companies, but I also get to access their knowledge (and the concentric knowledge of Newcastle's partners and the collaborator network) to see consumer trends materialize before I otherwise would.

What was your childhood career dream and how different is it from what you’re doing now?

I wanted to be David Letterman. While hosting team meetings now, I sometimes pretend I am (in my head at least).

What's your most specific pet peeve that no one else seems to understand?

The lack of headphones in public!

What's your go-to karaoke song?

“Should've Been a Cowboy” by Toby Keith