Short-term rental operators are using AI at some level. But 60% of leaders are frozen — convinced they need greater AI skills, without a plan to start real Agentic Integration. The AI Lab is where vacation rental managers learn, benchmark, and deploy it with vetted peers — curated by STR Directors MasterMind.
Paddle in too early and you're building on technology that wasn't as accessible — six months ago, agents were demos that couldn't be trusted with real work. Wait too long and you're chasing foam behind a wave that already broke. Agentic AI — software that doesn't just answer questions, it does the work — just crossed from demo to workhorse. The takeoff window is open right now.
Catch a wave at the right moment and it does most of the work for you. The AI Lab is how you time it — with vetted peers, a live benchmark, and a chairman watching the horizon.
Paddle out — join the AI Lab →The wrong PMS migration. The owner contract you underpriced for three years. The ordinance fight you saw coming too late. None of these show up in your P&L as "decided alone" — but that's what they cost you.
Every seat is held by someone running a professional vacation rental company — and no two members of a cohort share a market. That's the rule that makes the trust possible.
"You join a group for who is NOT in the room, as much as you do for who is in the room."
Joe Polish — founder of Genius Network, on why vetting matters
Not every applicant is offered a seat — candidates are weighed on revenue, experience, and market. The vetting is the product: it's why members speak freely and why the advice is worth taking.
"AI made almost everything cheaper — except trust. Trusted rooms are the new moat."
Tristan Webb — Chairman, STR Directors
I grew a Park City business to 96 luxury ski homes and sold it to Vacasa. I served on the VRMA board, co-chaired its government and public relations committees, and wrote a short-term rental ordinance my own city adopted. I've been the operator making the lonely call late at night — and I've been the advisor in the room when someone else had to make theirs.
What I learned is simple: nothing improves a decision like a table of peers who know your business and expect you to show up. Carnegie had that table. So did Edison and Ford. I built STR Directors so a vacation rental manager in Gatlinburg or Kauai could have it too — without needing a billionaire's rolodex to get in the room. My seat comes with three jobs above the rest: curating the right people into the right groups, keeping every meeting a room built on trust, and watching the horizon — so nothing breaks over this table unannounced.
Bring us the decision you're facing right now. That's how every member started.
"By far the most impactful ROI I've ever seen for professional vacation rental managers."
Brooke Pfautz — founder of Vintory, author of Vacation Rental Secrets
"Tristan is someone whose opinion I value and seek out when confronting obstacles and challenges in business. He doesn't tell you what to do — he leads you to discovery."
"It's been a huge value add for my business. If you're serious about scaling a vacation rental business, the mastermind is well run, high-value, and absolutely worth the time."
"I look forward to each session knowing I will have practical takeaways that I can immediately apply at my company."
"I too have been in this industry a long time, but I write over a page of notes every time we meet."
"Tristan is a master facilitator. He knows exactly how to match personalities and hold a safe space for the group."
"I have the utmost respect for his experience, knowledge and leadership, and am fortunate to have benefitted from this directly."
"He made a valuable resource an invaluable part of our strategic plan. I look forward to all my interactions with Tristan."
"Tristan's knowledge and experience of the vacation rental industry is immeasurable."
"His communication is excellent and thorough. He helps us stay on task. I highly recommend Tristan."
"Tristan is someone whose opinion I value and seek out when confronting obstacles and challenges in business. He doesn't tell you what to do — he leads you to discovery."
"It's been a huge value add for my business. If you're serious about scaling a vacation rental business, the mastermind is well run, high-value, and absolutely worth the time."
"I look forward to each session knowing I will have practical takeaways that I can immediately apply at my company."
"I too have been in this industry a long time, but I write over a page of notes every time we meet."
"Tristan is a master facilitator. He knows exactly how to match personalities and hold a safe space for the group."
"I have the utmost respect for his experience, knowledge and leadership, and am fortunate to have benefitted from this directly."
"He made a valuable resource an invaluable part of our strategic plan. I look forward to all my interactions with Tristan."
"Tristan's knowledge and experience of the vacation rental industry is immeasurable."
"His communication is excellent and thorough. He helps us stay on task. I highly recommend Tristan."
Most operators start with the AI Lab — lower commitment, faster wins, benchmarked against real peers. Catch the wave at the right moment and it does most of the work for you. When you're ready for the full board experience, the MasterMind is where the transformation happens.
Five minutes to apply. A real conversation with Tristan. A seat among operators who expect you to show up — and a chairman who curates the seats, protects the room, and watches the horizon.