Jeramie Worley

A Missouri operator who has spent two decades at the intersection of real estate and hospitality. He and his wife Kelly started acquiring and running short-term rentals in 2006 — before Airbnb existed — and rode the model through the worst real estate economy in modern history. He published one of the first books on investing in Airbnbs in 2016, then scaled from single properties into regional development. Today he's the lead on an $81M, 60-unit short-term rental syndication on Table Rock Lake, holds two and a half acres on the south coast of Kodiak, Alaska, earmarked for a fishing retreat, and co-owns Lake Longbow — an 80-acre Ozarks property with a 10-acre private lake that he and his partners bought just after COVID and have spent five years turning into a private executive retreat.

Jeramie grew up a self-described redneck from the Ozarks, summering at a family cabin on Lake of the Ozarks that his parents bought in with his grandparents — the memories he's now trying to recreate for his own kids. He didn't hunt at all until he was about 40; his dad and grandpa never did. What he found instead of a hobby was a reset button. He's candid that his family had margin forced into their lives by a child's medical issues, and that the experience is what made hospitality personal rather than transactional. He's a Christian who teaches multiple discipleship training classes a year, calls it marketplace ministry, and never goes to the property without something to read that isn't a phone — a journal, a Bible, or the copy of Walden he keeps out there.

Jeramie is building a category most operators don't see: luxury hunting hospitality for executives who have never been in the woods. His thesis is that the value isn't the deer — it's what happens when you take a high achiever, strip away the thing they're expert at, and hand them a white belt. He's unusually honest about the economics: Lake Longbow doesn't cash flow like a syndication, some years he subsidizes it, and the well alone may cost another $40K. He's equally clear about why he does it anyway — it's a legacy property, the relationships built around the campfire have turned into multi-million-dollar deals he never went looking for, and the physical work is the only thing that resets him for Monday. His operating advice is Y-Combinator blunt: if you're not embarrassed by your first product, you haven't launched fast enough — so turn the water on and find out where it leaks.