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VRS687 - Fewer Sessions, More Action at the Direct Booking Success Summit

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This Episode is Sponsored by The Simon Lehmann Academy

Simon Lehmann STR Academy is a self-paced course for property managers growing from around 20 to 200 homes and beyond. Built around the journey “From Operator to CEO,” it includes nine modules and 52 episodes covering the operating model, contracts, KPIs, unit economics, tech stack and exit readiness. It’s designed to help professional short-term rental operators build the structure needed to scale beyond a founder-dependent business.

Visit - Simon Lehmann's STR Academy

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Every Fall, a few weeks before the Direct Booking Success Summit, I sit down with Jenn Boyles, the host who created it. This is Jenn's fourth visit to the show, and this year we start somewhere unexpected: with Jenn explaining why she cut her own event almost in half. Last year's summit ran 47 sessions for around 1,000 hosts from more than 40 countries. People left with pages of notes, and Jenn started to wonder how many of them would act on any of it.

We also talk about Airbnb's new "direct booking link" for hosts and why Jenn says it is nothing of the kind, how she runs her one-person business with a team of named AI agents, and how AI has found its way into this year's program through sessions on AI search, channel profitability and building an AI business brain.

The 2026 summit runs online from November 17 to 19. If you manage short-term rentals and want three days that end with something done rather than a notebook full of good intentions, this conversation will help you plan for it.

About Jenn Boyles

Jenn Boyles is the founder of Direct Booking Success and the creator of the Direct Booking Success Summit, the free online event she has run every November since 2021. She started hosting in Europe in 2012, learned from a chalet in the Austrian Alps that wouldn't book, that a listing on a crowded platform isn't a business, and opened the Liverpool Boat in 2019 at 80% direct bookings. When the mass cancellations hit in 2020, her calendar held. Now based in Vancouver, she helps hosts and property managers build their own marketing through the STR Content Lab and the DBS Control Room, where clients build teams of AI agents to take on the work that doesn't need them personally.

Key takeaways

  • If every booking comes through one platform, you are an accommodation provider to that platform. A business you can rely on needs more than one source of guests.
  • Airbnb's new host "direct booking link" carries a lower commission, but the guest, the booking and all the communication stay on Airbnb. A true direct booking comes through your own website.
  • More information doesn't change a business, action does. Jenn's advice for the summit is to pick a day, pick a theme and do one action.
  • Before you build AI agents, give them a foundation. Jenn starts every client with their brand, voice, goals and business detail, then a task audit of everything they do that doesn't actually need them.
  • Agents only know what they can see. One Control Room member's "no bookings today" report turned out to be her deleting the booking emails before the agent could read them.
  • The fundamentals of direct booking marketing haven't changed: local content, blog posts and a strong website. AI search rewards the same work, done well.

Resources and links mentioned

Connect with Jenn Boyles

If this conversation sparked something, Jenn would love to hear from you, and the summit is the easiest place to start.

Who's featured in this episode?

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