Episodios

  • Direct Bookings, AI Agents & Why Airbnb Fees Are Going to 20% | Mark Simpson Returns

    Direct Bookings, AI Agents & Why Airbnb Fees Are Going to 20% | Mark Simpson Returns
    Jun 1 2026
    🔥 LAST CHANCE — STR AI SUMMIT, June 23-24 | Freedom Factory, Beverly, MAOnly 20 seats left. Use code "PODCAST" for a flat $1000 discount:👉 strsecrets.com/aisummitThe coupon expires MondayThis is where direct bookings, AI agents, and the next decade of STR get built — live, with the operators leading the charge.Yorkshire, UK — 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 — 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:→ Why Mark predicts Airbnb's commission is going from 15.5% to 20% — and what the data shows→ The 65% direct booking goal — and why going 100% direct is just as dangerous as 100% Airbnb→ The 3 things every direct booking website needs that 90% of operators still get wrong→ The exact story of Icarus: how Mark built his first AI agent in 2 days and made his money back in 7→ How Boostly went from a team of 20 to a team of 150 without hiring a single human→ Why 0.05% of people pay for AI Pro — and how $18 a month puts you in the top 99.5% globally→ The "18 minutes a day" rule that quietly turns operators into AI power users→ How Mark trained his entire 22-person team on AI without overwhelming a single person→ The honest answer to "are you teaching your team to replace themselves?"→ Why "the cream rises to the top" — and which roles are about to disappear🎙️ Guest: Mark Simpson | Founder, Boostly🔗 Website: https://www.boostly.co.uk🔗 Boostly Connect: https://boostlyconnect.com🔗 LinkedIn: Mark Simpson🔗 Instagram: https://www.instagram.com/boostlyuk🔗 Facebook: https://www.facebook.com/mrmarksimpson🔗 Book recommendation link: http://bit.ly/2WEOm1v─────────────────────────────⏱️ TIMECODES─────────────────────────────00:00 - The $50K wasted on human setters and the AI agent that changed everything01:32 - Mark Simpson returns for his record-breaking 7th episode02:15 - Life update: 4 kids, World Cup tickets, and the UK trip this summer03:29 - "Don't build your home on someone else's land" — Mark's signature line04:00 - Airbnb's fee hike from 3% to 15.5% — and why he saw it coming in 202204:30 - The next prediction: why Airbnb is going to 20% commission06:38 - Top 3 things every operator needs to start direct bookings TODAY07:02 - 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 revenue11:51 - What does "good" look like? The 65% direct booking benchmark13:49 - The two-part myth: high-converting website AND content/SEO effort14:27 - Why hospitality operators are spoiled — and why that's a problem16:40 - The fundamentals of business that STR operators keep ignoring17:26 - The "do you know anyone" referral mindset most operators are too scared to use19:55 - The mirror moment: who do you actually blame for missing your goals?20:36 - AI agents — Mark's full breakdown starts here20:57 - Why The Matrix in 1999 still defines how Mark thinks about AI22:00 - The OpenClaude story: how one weekend GitHub project broke the industry open24:50 - The breaking point: firing the $50K setter and going all in25:30 - Meet Icarus — 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 costs26:30 - 18 agents, $54,000 in revenue, 2 months later27:19 - Reality check for the shiny object chasers29:00 - "I'm an idiot" — Mark on why anyone can do this30:00 - All 22 Boostly employees now have their own AI agent31:30 - The Google Chrome extension a non-technical team member built in one week33:00 - 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 mastery35:00 - How Mark rolled AI out to his team without overwhelming anyone36:30 - Comet by Perplexity: the agentic browser changing how teams work38:04 - "Aren't you teaching them to replace themselves?" The hard question38:55 - Mark's ...
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    50 m
  • The AI Comp Tool That's Getting STR Managers 7 Sales Calls a Week

    The AI Comp Tool That's Getting STR Managers 7 Sales Calls a Week
    May 28 2026

    Ryan will be showing how to make this and a custom revenue management tool live at the Ai Summit. Grab your spot at the AI Summit: strsecrets.com/aisummit at just $497. Use the coupon : "PODCAST"

    Every homeowner conversation starts the same way.

    They want to know what their property can earn.

    And if you can't answer that question fast, professionally, and with data behind it —

    someone else will.

    In this week's training, Mike sits down with STR Secrets coach Ryan Lefebvre to

    demo the AI-powered comp analysis tool that's helping property managers turn more

    conversations into signed contracts.

    Ryan went from 1-2 comp requests a week to 10 a week — from realtors and investors

    who now send him every new listing because he delivers branded, data-backed reports

    in minutes, not hours.

    In this episode:

    → The exact tool Ryan built using Claude that generates a full comp report in

    2 to 10 minutes (vs. 20-30 minutes manually)

    → How to use conservative, base, and optimistic revenue projections to handle

    any homeowner conversation on the spot

    → Why realtors are becoming one of the fastest referral pipelines for new

    management contracts — and how to tap in

    → The AI rabbit hole warning: why building your own tools can quietly kill

    your business growth

    → Mike's financial freedom math: exactly how much you need invested to hit

    $100K a month in cash flow

    → Why arbitrage is a dead end — and what the data on the biggest arbitrage

    companies actually shows

    This is not theory. Ryan runs live comps during the session on real properties

    submitted by the audience — you'll see exactly how the tool works in real time.

    Want the comp tool? DM COMP at mike.sjogren

    and we'll send it straight to you.

    Ready to install this and a full AI system for your business live?

    Timestamps:

    00:00 - Intro & Ryan Lefebvre's background

    01:42 - From financial crime analyst to AI builder for STR

    04:22 - How the comp tool works and what it produces

    06:33 - Live demo: running an Airbnb listing in real time

    09:26 - Interactive sliders and revenue scenario conversations

    11:17 - How to handle bad comps and sparse markets

    13:36 - Live demo: running a property address

    17:34 - How the tool handles off-market or renovated properties

    22:38 - Using comp reports to show homeowners the gap between unmanaged and managed

    26:41 - AI Summit: what's being covered and who's speaking

    29:04 - Ticket pricing and how to register

    32:02 - Alex case study: 2 properties to 35 in one year

    35:29 - The AI rabbit hole warning

    38:00 - Using AI at any portfolio size

    41:06 - Mike's financial freedom math ($8M at 15% = $1.2M/year)

    44:46 - Why arbitrage is a dead model

    49:27 - Should you replace your channel manager with AI? (No. Here's why)

    52:45 - Q&A: summit details, recordings, revenue manager AI tool
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    59 m
  • Why Your STR Business Stopped Growing (And It's Not the Market)

    Why Your STR Business Stopped Growing (And It's Not the Market)
    May 25 2026

    🔥 Get $500 off at STR AI SUMMIT — June 23-24 | Freedom Factory, Beverly, MA

    Use code "MEMORIAL500" while checking out at strsecrets.com/aisummit

    You're doing the work. You're managing the properties. You're showing up every day.

    So why does it feel like you're spinning your wheels?

    In this solo show, Chris Petzy and Emanuele Pani get raw about the real reason STR

    operators stall out — and it has nothing to do with the market, your pricing strategy,

    or your occupancy rate.

    In this episode:

    → The 3 silent causes of business stagnation (and which one is quietly killing your

    growth right now)

    → Why split focus will never equal scale — and the one decision Chris made that

    changed everything

    → The identity gap: how to stop making decisions from who you've been and start

    making them from who you're becoming

    → E's 5 daily affirmations that rewire how you start every single day

    → Why hiring for today's need is the biggest mistake scaling operators make

    If the last six months didn't go the way you planned, this episode is your reset.

    Ready to build the business that funds the life?

    Apply to work with us: strsecrets.com/apply
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    38 m
  • She Built an AI Agent That Creates 10 Carousels From One Airbnb Link | Dr. Rachel Gainsbrugh

    She Built an AI Agent That Creates 10 Carousels From One Airbnb Link | Dr. Rachel Gainsbrugh
    May 21 2026
    Get Carrie the AI Carousel Sniper Agent: https://level.strsecrets.com/drrachel🔥 STR AI SUMMIT — June 23-24 | Freedom Factory, Beverly, MADr. Rachel is flying in to spend 2 full hours building this exact system with you live.You won't just learn it. You'll leave with it installed. Only 70 seats left. 👉 strsecrets.com/aisummitMost STR operators know they need to post more. They just don't have the time, the team, or the system to do it.Dr. Rachel Gainsbrugh does. And in Portfolio Clinic Episode 8, she pulls back the curtain on the exact AI content engine she built to generate weeks of social content without living on her phone.Dr. Rachel is a former full-time physician turned full-time real estate investor, entrepreneur, AI strategist, and founder of Short Term Gems. She built her entire content system out of necessity — and now it runs largely without her.In this episode, Mike Sjogren sits down with Dr. Rachel to walk through the full system live: from raw meeting notes to scheduled carousels, with AI agents doing most of the heavy lifting.What you'll learn:→ The 7-11-4 rule: why buyers need 7 hours of content across 11 touchpoints on 4 platforms before they trust you enough to write you a check→ Meet Vega — the AI agent that processes all your meeting notes every night and sorts them into content, SOPs, and coaching opportunities before you wake up→ Meet Carrie — the carousel sniper that takes one Airbnb link and delivers 10 ready-to-post carousels including captions and CTAs→ Meet Contesta — the content queen that formats everything for each platform and sends it to scheduling automatically→ How a property manager with 80 doors sent 60 personalized owner emails in 2 hours (he used to spend his whole weekend on it)→ How to train your AI like an employee using SOPs — and why that one step changes everything→ The AI data privacy protocol that keeps your sensitive files in a sandbox and out of reach→ Why posting once or twice a week means you are already losing to operators using this system🎙️ Guest: Dr. Rachel Gainsbrugh | Founder, Short Term Gems🔗 Get Carrie the Carousel Sniper Agent: https://level.strsecrets.com/drrachel─────────────────────────────⏱️ TIMECODES00:00 - Cold open: Carrie the carousel sniper demo — one Airbnb link, ten carousels00:57 - Mike and Dr. Rachel intro — why she's the go-to AI person in the space01:34 - Dr. Rachel's background: from full-time doctor to AI-powered STR investor02:13 - The 7-11-4 rule: the Modern Trust Formula every operator needs to understand03:04 - Two content angles for STR operators: repeat guests and new client acquisition03:39 - Why Dr. Rachel built this system (she hates being on camera)05:24 - The note taker habit that turns every meeting into a content asset05:48 - The Plaud Note Pin: the wearable AI recorder Mike and Rachel swear by07:09 - Meet Vega: the AI night agent that sorts all your meetings while you sleep07:53 - How Vega triages every meeting into four buckets before you wake up08:15 - Real demo: Vega identifies a coaching frame used 14 times across calls and flags it09:23 - 425 meetings reviewed by AI that no human ever had time to touch09:56 - How Vega processes data directly from Fireflies, Otter, and Plaud using schema13:22 - Step two: turning the content database into actual social posts with Contesta13:58 - Real proof: 80-door property manager sends 60 personalized owner emails in 2 hours14:22 - How Contesta routes content to Phoebe (Facebook) and schedules it automatically15:15 - How Mike applies this to property walkthroughs and hotel renovation updates16:14 - Why guest reviews are an untapped content goldmine most operators ignore17:20 - The one thing Dr. Rachel warns against: asking AI to write posts with no context18:05 - How to sell through your real stories: the three-part owner acquisition framework19:15 - Mike's local events agent: scraping tourism data to feed newsletters and social20:18 - Why showing your journey (not the polish) is what builds trust and drives bookings21:46 - Meet Carrie: the carousel sniper — live demo walkthrough23:11 - Carrie in action: pulling property photos from Airbnb, building 8-10 slide carousels24:50 - Guest reviews as carousel slides: 122 reviews turned into content automatically25:29 - Carrie delivers: full carousel batch plus caption, CTA, and downloads folder26:00 - Is all of this through Claude? Yes — Claude Co-Work and Claude Code27:04 - How long it took to build Carrie (two months) and how fast it runs now (one command)28:44 - Train AI like an employee: the SOP-first method for consistent results29:49 - Real world result: executive assistant elevated from admin to EA after AI frees her up31:47 - Dr. Rachel is speaking at the AI Summit — two full hours of live building with you33:43 - How to train Claude with SOPs, PDFs, and audit loops35:26 - AI quality is only as good as your SOP —...
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    50 m
  • $1B STR Company CEO Tells You Exactly How AI Will Eat Your Business (Or Make You Rich) | Marcus Räder, Hostaway

    $1B STR Company CEO Tells You Exactly How AI Will Eat Your Business (Or Make You Rich) | Marcus Räder, Hostaway
    May 18 2026
    🔥 STR AI Summit — June 23-24 | Freedom Factory, Beverly, MAOnly 100 seats. Built for operators who are serious about what comes next.👉 strsecrets.com/aisummitIf you're managing 5, 10, or 50+ properties and wondering whether AI is a tool or a threat — Marcus Räder has the answer. And it's not what most people are saying.Marcus is the co-founder and CEO of Hostaway — the first vacation rental software company to reach unicorn status and the recipient of the largest funding round in vacation rental history: $365 million led by General Atlantic.He's been in this industry for over a decade. He's seen every wave. And right now, he's more excited — and more concerned for unprepared operators — than ever before.In this episode, E and Chris sits down with Marcus for one of the most candid, far-reaching conversations in the show's history. From AI and private equity to running 100 marathons in 100 cities — this one goes deep.What you'll learn:→ Why private equity is circling STR operators right now and what it means for your business valuation→ The #1 thing AI can't do for your properties (and where most operators are dangerously overconfident)→ Why "more data = more visibility" is the new SEO — and how to make your listings AI-search-proof→ The direct booking strategy that still works in 2026 (the basics haven't changed as much as you think)→ How to build a team that thinks 3 years ahead when they're wired to think about today→ The honest truth about building a big business vs. just being great at your job→ What losing 70 pounds and running 17 marathons taught Marcus about scaling anything🎙️ Guest: Marcus Räder | Co-Founder & CEO, Hostaway🔗 Connect: https://www.linkedin.com/in/marketingmarcus/🌐 Website: hostaway.com─────────────────────────────⏱️ TIMECODES─────────────────────────────00:00 - The hard truth: adapt to AI or lose guests to someone who did02:01 - E & Chris reconnect — scaling conference takeaways + the Sardinia deal update05:39 - Introducing Marcus Räder: building Hostaway into a $1B business08:50 - Living the hybrid US-Europe life with family (7 months abroad)11:48 - Hostaway's origin story: from channel manager to full PMS to $365M raise14:03 - What it actually feels like to run a unicorn — the founder's relationship with time16:20 - How to build a team that thinks years ahead when employees focus on today17:34 - Why Marcus's best hires came from web hosting, not STR19:37 - AI in STR: excited or worried? Marcus's honest take from the CEO seat21:47 - The viral meme that perfectly exposes the DIY AI trap22:45 - What STR operators really do during peak season (it's not what you think)23:06 - Where AI fails: raccoons, hurricanes, guest injuries, and edge cases24:15 - How Hostaway built its AI control layer for guest communications27:00 - Build in-house vs. stay third party: Marcus's framework for scaled operators28:33 - The hidden danger of AI models that silently update and change answers29:41 - The Uber lesson every STR operator needs to hear right now31:25 - Will AI become a race to the bottom? Where monetization is heading32:07 - The pool pump disruption: how AI reshapes maintenance costs and who profits34:00 - "Findability" — go ask AI to find YOUR property right now and see what happens35:15 - Why private equity is turning STR businesses into 10x assets with AI36:18 - What the next decade of Hostaway looks like38:33 - Direct bookings in 2026: the dead-simple strategy most operators still skip39:26 - Why your listing description is failing AI search (and the wall of text fix)41:42 - Data is the new currency: whoever gives AI the most wins the booking42:13 - Build big or go work for someone — Marcus's hard truth about entrepreneurship43:13 - 100 marathons in 100 cities: the health journey and what flat feet taught him47:07 - The calorie analogy that explains how small disciplines compound at scale49:36 - Marcus's #1 secret to STR success: boring, consistent, and most people skip it─────────────────────────────🎁 FREE RESOURCES─────────────────────────────Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-bookSTR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets─────────────────────────────#ShortTermRental #AirbnbInvesting #STRSecrets #VacationRental #PropertyManagement #STRScaling #AIforSTR #Hostaway #DirectBookings #RealEstateInvesting
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    52 m
  • The Real Truth About AI for STR Operators — What Works, What Doesn't, and What It Actually Costs

    The Real Truth About AI for STR Operators — What Works, What Doesn't, and What It Actually Costs
    May 14 2026

    Join use at the STR AI Summit — June 23-24 at the Freedom Factory in Beverly, MA. 100 seats only strsecrets.com/aisummit

    Mike Sjogren spent over $5,000 in API credits in two months learning AI the hard way. And he wants to make sure you don't have to.

    In this Portfolio Clinic training, Mike breaks down the top 10 AI mistakes that cost him real money — from not understanding context windows to memory file bloat to giving an agent 15 tasks at once and wondering why nothing got done. He then walks through exactly how STR operators should be using AI right now across three buckets: getting more properties, getting more bookings, and getting more time back.

    He also shows how he rebuilt his Florida direct booking website in under a day for under $200 using Manus, how his AI agent scrapes top boutique hotel social media content overnight and delivers a morning brief, and why the goal is never to build your own software — it's to use AI as a bolt-on to everything you already have.

    DM Mike on Instagram @mike.sjogren and comment PROMPT to get the free PDF of all the prompts he used to build his direct booking website.

    STR AI Summit — June 23-24 at the Freedom Factory in Beverly, MA. 100 seats only.

    strsecrets.com/aisummit

    Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

    STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

    Timestamps:

    0:00 - Why Mike Is Doing This Training (And How Much It Cost Him)

    2:15 - Mistake #1: Not Understanding Context Windows ($6 Per Message)

    5:30 - Mistake #2: Memory File Bloat — Why AI Gets Dumber Over Time

    7:45 - Mistake #3: Using Your Most Expensive Model for Everything

    10:00 - Mistake #4: Broken Cron Jobs — How to Schedule Tasks That Actually Run

    13:00 - Mistake #5: Treating AI Like an Employee Who Can Handle 15 Things at Once

    16:30 - Mistake #6: Not QC-ing the Output

    18:00 - Mistake #7: Trying to Build Your Own PMS or Pricing Tool

    20:30 - The 3 STR Buckets: More Properties, More Bookings, More Time

    23:00 - How to Use AI to Automate Your Entire Prospecting Pipeline

    27:00 - How to Use AI to Get More Bookings Right Now

    30:00 - How to Rebuild Your Direct Booking Website With AI for Under $200

    36:00 - How Mike's Overnight Agent Scrapes Top Hotel Content Every Night

    39:00 - The 10 Rules for Using AI Without Burning Your Budget

    42:00 - How to Motivate Your Team to Use AI Without Fear

    46:00 - Where to Start If You're Brand New to AI

    48:00 - STR AI Summit: June 23-24 at the Freedom Factory
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    54 m
  • Buying Facilities for $40K a Door: Why Senior Housing is the Next Major Real Estate Wave

    Buying Facilities for $40K a Door: Why Senior Housing is the Next Major Real Estate Wave
    May 11 2026

    🎟️ Join us at the STR AI Summit — June 23-24 at the Freedom Factory in Beverly, MA.

    Only 100 seats. Early bird: $1,497.

    strsecrets.com/aisummit

    Tying your identity to your door count is the fastest way to burn out—or worse. In 2008, Rod Khleif lost $50 million. He calls it an expensive "seminar."

    In this episode, E sits down with Rod to discuss how he rebuilt his massive real estate portfolio by fundamentally changing his peer group and his mindset.

    Today, Rod's students own over 260,000 units, and he has fed more than 160,000 children through his Tiny Hands Foundation. He breaks down the massive demographic shift he calls the "Silver Tsunami"—why the demand for senior housing is about to explode, and how his team is acquiring assisted living facilities for $40,000 a door.

    He also shares a massive wake-up call regarding Artificial Intelligence, explaining exactly how his own marketing team is using Claude AI to replace 95% of their manual workload.

    Connect with Rod Khleif:

    Website: http://Rodkhleif.com

    Podcast: Lifetime Cash Flow Through Real Estate Investing

    Instagram: https://www.instagram.com/rod_khleif/

    Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

    STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets
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    42 m
  • The Exit Strategy Most STR Operators Don't Have — And Why It's Costing Them Millions

    The Exit Strategy Most STR Operators Don't Have — And Why It's Costing Them Millions
    May 7 2026

    Join us at The STR AI Summit is June 23-24 at the Freedom Factory in Beverly, MA.

    100 seats only. Grab your ticket: https://www.strsecrets.com/aisummit

    Most STR operators have built a great lifestyle business. But here's the hard truth: only 1 in 10 businesses will ever successfully sell. The rest close and walk away with nothing.

    In this Portfolio Clinic training, Mike Sjogren breaks down exactly how STR management companies are valued — and what operators need to start doing right now to build a business with a real exit strategy.

    He walks through the EBITDA formula, the exact valuation metrics used by C2G Advisors (the top M&A firm in the STR industry), why rental arbitrage and co-hosting businesses get little to no value from buyers, and why private equity has been quietly acquiring STR management companies since 2022.

    He also introduces the Freedom Collective — STR Secrets' own roll-up model designed to give operators a share of the upside instead of selling to private equity at a discount. And he breaks down how AI agents can automate an entire acquisition pipeline from property data scraping to sales call booking.

    Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

    STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets
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    58 m