I'm a 40-something innkeeper, STR manager, designer, leader, dirtbag runner, currently operating across eleven states and two countries. My ideal partner-in-conversation can bake blueberry crunch muffins from scratch, has used a hotel front desk as kindling for a bonfire, learned the difference between a guest "concern" and a guest "complaint", and knows the specific vibe of helping a guest at 11pm because… little Tommy shit the bed.
You should also ideally enjoy long walks on the beach (crying), the smell of dryer sheets at 7am, and the kind of conversation that begins "OK whatever, but what I wanna know is how many male prostitutes have you bounced from your Motels this year?"
Bonus traits include knowing how to get Cheez Wiz off of a couch cushion and enjoying belly laughs about those times when you got spray foam in your hair or glued your foot to your slipper with liquid nails.
Asking, of course, because I don't get enough of these conversations. And I suspect based on the operators I do meet, when I meet them… that none of us do.
Here's the part that's sad, funny and strange: hospitality is the only industry whose entire product is human connection. We rent the feeling of being welcomed. We sell the difference between a stranger walking through a door and a guest who feels expected. We hire for warmth, train for grace, and grade ourselves on whether a person we'd never met before leaves feeling like they were seen.
Yet we are terrible at connecting to each other.
We shouldn't be. We have the same questions. We're hitting the same walls in different rooms.
Where you'd expect the connecting infrastructure to be, there are three broken things in its place.
The conference is a vendor trap. I have nothing against the major industry conferences. I've spoken at a few, I'll be at a few more. But for $3,000 to $5,000 a trip, the median operator leaves with a tote bag of demos for software they didn't ask for, two business cards from people selling pricing tools, and four follow-up emails the next week from sales reps. Real operator-to-operator conversation happens in the elevator and at the bar at midnight. But I don't drink anymore and I only see midnight when I'm running 100k and haven't finished when the clock strikes 12. But even if you are at the bar….. Are you extroverted enough to fit in or start that conversation? Very few of us are unless we are perfectly lubed by the 80 proof.
LinkedIn is broken for operations talk. Open the app tomorrow and count how many posts in your feed are an actual operator describing what they did in a property last week. Then count how many are vendors selling AI tools, agencies announcing partnerships, or thought-leadership pieces written by someone who has never been on the wrong side of a clogged drain on a Saturday morning. The signal-to-noise has tilted, and we let it.
The segment silos are also not the answer. If you run a short-term rental portfolio, your "industry" is VRMA, VRM Intel, AirDNA, the AirBnB hosts subreddit. If you run a small boutique hotel, it's AHLA, Hotel Dive, Skift. If you run a roadside motel (or ten) like I do, among other things, almost no one is writing for you at all. The lessons that travel best are the ones that cross these lines: the check-in flow a boutique hotelier perfected is exactly what a 12-door STR portfolio needs. The pricing instinct an STR operator developed in 2021 is exactly what an inn could use in 2026. But the rooms we sit in to learn don't overlap.
I don't think the answer is another conference. I think it's smaller and quieter than that. Jimmy Bizly if you are reading this, yes I'm going to bring back NAVRM (in your honor) but we are adding hoteliers too.
What I'd love more of: cohorts of six or eight operators, across segments, on a phone call every six weeks or better yet at one of our properties, there to solve a few issues. Honest. Off-record.
"Here's what's working, here's what isn't, here's the thing I haven't told anyone else yet."
No vendor pitches. No agenda. No deck. The format already exists in finance (YPO, Vistage), in tech (the founder dinners that happen in every city), in basically every industry that's serious about peer learning, except, somehow, in the industry whose entire job is making strangers comfortable in a room together.
I'd love more honest invitations like this one. Not "networking." Not "let's grab coffee" in the LinkedIn-platitude sense. Real conversations between people who know what the work actually costs and what needs fixing. "Billy, I need your help with XYZ, get your ass over here and help me fix it." Or "can you come stay in this room and that room and tell me why this one has a much better rating?"
So consider this the invitation. I'll drive it, organize it, all of the above… but I need you. I'm bloody tired of talking to myself.
Me? I'm an operator. I run inns and rentals in Maine, Vermont, Arizona, Utah, Idaho, Colorado, Costa Rica, Hawaii and a few other places along the way. I came up through STR when we traded checks for keys (the 90's were so rad), ran a multi-country European vacation-rental group for a few, and recently went back to small properties I own and design, because I missed the connection with the guest.
I'm not selling anything. I have no consulting practice. The newsletter I write is mentioned at the bottom of this article precisely once, and only because the publisher requires a bio.
I am, however, genuinely interested in the next conversation. Especially if you run something small enough that you still know the names of your housekeepers, or something just big enough that you don't quite know how many kids they have, or you're somewhere on the path between those two and trying to figure out how to keep the warmth as you scale.
My email is in the bio. Please use it.
Aloha,
Billy O'
Billy O'Sullivan is Principal at Ohana Vacations, co-founder of Ohana Inns and owns Kauai Vacation Group, with properties across Hawaii, Maine, Oregon, Colorado, Idaho, Utah, Arizona, Vermont, Georgia, Costa Rica, and points in between.
He writes The Check-In, an operator-to-operator newsletter at www.TheCheckIn.net.
Reach him at billyo@ohanavacations.com.
