π₯ LAST CHANCE β STR AI SUMMIT, June 23-24 | Freedom Factory, Beverly, MA
Only 20 seats left. Use code "PODCAST" for a flat $1000 discount:
π strsecrets.com/aisummit
The coupon expires Monday
This is where direct bookings, AI agents, and the next decade of STR get built β live, with the operators leading the charge.
Yorkshire, UK β Mark Simpson spent $50,000 on human appointment setters last year. They did almost nothing.
Then he built one AI agent named Icarus. In 7 days, it closed a $5,000 deal. Cost? Less than $20.
Two months later, Mark has 18 AI agents running inside Boostly. They've generated $54,000 in revenue. And he says he's never hiring a human setter again.
Mark Simpson is the founder of Boostly β the company helping STR operators escape over-reliance on Airbnb and own their direct bookings. He grew up on a farm in North Yorkshire, where his family ran a BNB. Over the last decade, he's refined the most complete direct bookings playbook in the vacation rental industry. Now on his 7th appearance on the show, he's back with the rawest, most honest take on AI agents we've had to date.
This is his blueprint for direct bookings, AI agents, and what's about to happen to operators who don't adapt.
What you'll learn:
β Why Mark predicts Airbnb's commission is going from 15.5% to 20% β and what the data shows
β The 65% direct booking goal β and why going 100% direct is just as dangerous as 100% Airbnb
β The 3 things every direct booking website needs that 90% of operators still get wrong
β The exact story of Icarus: how Mark built his first AI agent in 2 days and made his money back in 7
β How Boostly went from a team of 20 to a team of 150 without hiring a single human
β Why 0.05% of people pay for AI Pro β and how $18 a month puts you in the top 99.5% globally
β The "18 minutes a day" rule that quietly turns operators into AI power users
β How Mark trained his entire 22-person team on AI without overwhelming a single person
β The honest answer to "are you teaching your team to replace themselves?"
β Why "the cream rises to the top" β and which roles are about to disappear
ποΈ Guest: Mark Simpson | Founder, Boostly
π Website: https://www.boostly.co.uk
π Boostly Connect: https://boostlyconnect.com
π LinkedIn: Mark Simpson
π Instagram: https://www.instagram.com/boostlyuk
π Facebook: https://www.facebook.com/mrmarksimpson
π Book recommendation link: http://bit.ly/2WEOm1v
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β±οΈ TIMECODES
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00:00 - The $50K wasted on human setters and the AI agent that changed everything
01:32 - Mark Simpson returns for his record-breaking 7th episode
02:15 - Life update: 4 kids, World Cup tickets, and the UK trip this summer
03:29 - "Don't build your home on someone else's land" β Mark's signature line
04:00 - Airbnb's fee hike from 3% to 15.5% β and why he saw it coming in 2022
04:30 - The next prediction: why Airbnb is going to 20% commission
06:38 - Top 3 things every operator needs to start direct bookings TODAY
07:02 - Why WordPress still wins in 2026 (and why your PMS landing page isn't a real website)
08:54 - When to flip from "this is a hobby" to "this is a business" (around property 6-7)
09:30 - Why exit-ready businesses always have strong direct booking revenue
11:51 - What does "good" look like? The 65% direct booking benchmark
13:49 - The two-part myth: high-converting website AND content/SEO effort
14:27 - Why hospitality operators are spoiled β and why that's a problem
16:40 - The fundamentals of business that STR operators keep ignoring
17:26 - The "do you know anyone" referral mindset most operators are too scared to use
19:55 - The mirror moment: who do you actually blame for missing your goals?
20:36 - AI agents β Mark's full breakdown starts here
20:57 - Why The Matrix in 1999 still defines how Mark thinks about AI
22:00 - The OpenClaude story: how one weekend GitHub project broke the industry open
24:50 - The breaking point: firing the $50K setter and going all in
25:30 - Meet Icarus β Mark's first AI agent (and the Greek myth behind the name)
26:00 - Real result: $5,000 booking closed in 7 days for under $20 in AI costs
26:30 - 18 agents, $54,000 in revenue, 2 months later
27:19 - Reality check for the shiny object chasers
29:00 - "I'm an idiot" β Mark on why anyone can do this
30:00 - All 22 Boostly employees now have their own AI agent
31:30 - The Google Chrome extension a non-technical team member built in one week
33:00 - The $18 Pro plan stat: why 99.5% of the world isn't paying yet (and what that means for you)
34:00 - The 18 minutes a day rule that compounds into mastery
35:00 - How Mark rolled AI out to his team without overwhelming anyone
36:30 - Comet by Perplexity: the agentic browser changing how teams work
38:04 - "Aren't you teaching them to replace themselves?" The hard question
38:55 - Mark's brutally honest answer (it's not what you think)
41:27 - Why AI Agent Manager is the #1 role being hired for right now
41:51 - The danger of going 100% AI (same risk as going 100% direct)
43:21 - Life on the human side: paddle, books, and saying goodbye to soccer
44:43 - 6 hours back in his day β what Mark plans to do with it
46:55 - The two killers of every operator: lack of attention and poverty of imagination
47:41 - Boostly Connect β the free tool that pulls your PMS data anywhere
49:04 - Mark's #1 secret to AI agent success: just start
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π FREE RESOURCES
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Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book
STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets
Boostly Direct Booking Playbook (Mark's book): http://bit.ly/2WEOm1v
Boostly Connect (free up to 10 listings): https://boostlyconnect.com
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π₯ STR AI SUMMIT β June 23-24 | Freedom Factory, Beverly, MA
The exact AI systems Mark talks about in this episode? They get built with you LIVE at the summit.
Don't just listen to the playbook. Leave with it installed.
Only 100 seats.
π strsecrets.com/aisummit
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#ShortTermRental #DirectBookings #AIforSTR #Boostly #STRSecrets #VacationRental #PropertyManagement #AirbnbInvesting #AIAgents #STRScaling
