Jeramie Worley
Real Estate Developer & Hospitality Operator, Lake Longbow
An Ozarks landowner who didn't hunt until he was 40 and now builds the hunt for other people — whitetail off the ridge-top trail at Lake Longbow, black bass and crappie out of his own 10-acre lake, and a Kodiak fishing camp still on the drawing board.
- Short-Term Rentals
- Real Estate Syndication
- Hospitality Operations
- Luxury Hunting Retreats
- Land Development
About Jeramie Worley
What Jeramie built
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 in the field
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.
Why this conversation matters
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.
“Hospitality means that I've thought of you before you've arrived.”
Jeramie Worley on The Hunt for Success
Sam McGough's full conversation with Jeramie, available on YouTube, Spotify, and Apple Podcasts.
Key takeaways from Jeramie Worley
The ideas Jeramie left on the table in episode 13.
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Hospitality is thinking of someone before they arrive.
Jeramie's definition is the whole business in one line. Guests get a questionnaire before the weekend — food allergies, favorite snack, favorite drink, alcoholic or not — and it's all waiting when they show up. One guest with severe allergies told him he'd never felt more cared for, because separate meals were prepared for him without his having to ask.
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The market is the guy who's never been in the woods.
Jeramie found his edge in one-on-one conversations at masterminds: everyone vacations in Cabo, almost nobody takes ten days in November to disconnect entirely. Executive types who work with their brains have no outlet for working with their hands — and that gap, not the hunting itself, is the product.
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Take away the black belt and hand them a white one.
The reason the campfire works is that it strips away expertise. Take a high achiever who has to be on all the time, put him at something he's never done, and the guard drops in a way it never does in a conference room. That vulnerability is the actual deliverable.
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Don't program it — let the woods set the agenda.
There's no curriculum, no themed sessions, no invited speakers. Eight to twelve guys pair off, fish, hike, sit in stands, and end up at the fire. Two estranged brothers came out and the deer stand was the point, not the deer. Jeramie's job is to build the container and stay out of the way.