Short Term Rental Secrets Podcast

MICHAEL SJOGREN

The Short Term Rental Secrets Podcast is dedicated to providing actionable content to help new and seasoned real estate investors launch, automate and scale their Airbnb business and fast track their journey to financial freedom. You can enjoy the podcast and other free resources at www.STRsecrets.com

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

    6d ago

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

    🔥 LAST CHANCE — STR AI SUMMIT, June 23-24 | Freedom Factory, Beverly, MA Only 20 seats left. Use code "PODCAST" for a flat $1000 discount: 👉 strsecrets.com/aisummit The coupon expires Monday This 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 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" — Mark's signature line 04:00 - Airbnb's fee hike from 3% to 15.5% — 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 — 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 — 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 — 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" — 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 — 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 — the free tool that pulls your PMS data anywhere 49:04 - Mark's #1 secret to AI agent success: just start ───────────────────────────── 🎁 FREE RESOURCES ───────────────────────────── 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 ───────────────────────────── 🔥 STR AI SUMMIT — 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. 👉 strsecrets.com/aisummit ───────────────────────────── #ShortTermRental #DirectBookings #AIforSTR #Boostly #STRSecrets #VacationRental #PropertyManagement #AirbnbInvesting #AIAgents #STRScaling

    50 min
  2. The AI Comp Tool That's Getting STR Managers 7 Sales Calls a Week

    May 28

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

    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

    59 min
  3. She Built an AI Agent That Creates 10 Carousels From One Airbnb Link | Dr. Rachel Gainsbrugh

    May 21

    She Built an AI Agent That Creates 10 Carousels From One Airbnb Link | Dr. Rachel Gainsbrugh

    Get Carrie the AI Carousel Sniper Agent: https://level.strsecrets.com/drrachel 🔥 STR AI SUMMIT — June 23-24 | Freedom Factory, Beverly, MA Dr. 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/aisummit Most 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 ───────────────────────────── ⏱️ TIMECODES 00:00 - Cold open: Carrie the carousel sniper demo — one Airbnb link, ten carousels 00:57 - Mike and Dr. Rachel intro — why she's the go-to AI person in the space 01:34 - Dr. Rachel's background: from full-time doctor to AI-powered STR investor 02:13 - The 7-11-4 rule: the Modern Trust Formula every operator needs to understand 03:04 - Two content angles for STR operators: repeat guests and new client acquisition 03:39 - Why Dr. Rachel built this system (she hates being on camera) 05:24 - The note taker habit that turns every meeting into a content asset 05:48 - The Plaud Note Pin: the wearable AI recorder Mike and Rachel swear by 07:09 - Meet Vega: the AI night agent that sorts all your meetings while you sleep 07:53 - How Vega triages every meeting into four buckets before you wake up 08:15 - Real demo: Vega identifies a coaching frame used 14 times across calls and flags it 09:23 - 425 meetings reviewed by AI that no human ever had time to touch 09:56 - How Vega processes data directly from Fireflies, Otter, and Plaud using schema 13:22 - Step two: turning the content database into actual social posts with Contesta 13:58 - Real proof: 80-door property manager sends 60 personalized owner emails in 2 hours 14:22 - How Contesta routes content to Phoebe (Facebook) and schedules it automatically 15:15 - How Mike applies this to property walkthroughs and hotel renovation updates 16:14 - Why guest reviews are an untapped content goldmine most operators ignore 17:20 - The one thing Dr. Rachel warns against: asking AI to write posts with no context 18:05 - How to sell through your real stories: the three-part owner acquisition framework 19:15 - Mike's local events agent: scraping tourism data to feed newsletters and social 20:18 - Why showing your journey (not the polish) is what builds trust and drives bookings 21:46 - Meet Carrie: the carousel sniper — live demo walkthrough 23:11 - Carrie in action: pulling property photos from Airbnb, building 8-10 slide carousels 24:50 - Guest reviews as carousel slides: 122 reviews turned into content automatically 25:29 - Carrie delivers: full carousel batch plus caption, CTA, and downloads folder 26:00 - Is all of this through Claude? Yes — Claude Co-Work and Claude Code 27:04 - 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 results 29:49 - Real world result: executive assistant elevated from admin to EA after AI frees her up 31:47 - Dr. Rachel is speaking at the AI Summit — two full hours of live building with you 33:43 - How to train Claude with SOPs, PDFs, and audit loops 35:26 - AI quality is only as good as your SOP — garbage in, garbage out 36:31 - Who owns your property photos? What every operator needs in their photographer contract 37:19 - The Night Janitor: the AI agent that organized 16,000 photos and files in minutes 39:15 - How to talk to Claude about your messy photo library and get a real solution 41:05 - Claude Code vs. Claude Co-Work: when to use which for scheduling and automation 41:35 - Should you have separate social accounts for owner acquisition vs. guest direct bookings? 43:49 - Training AI vs. training humans: why right now is the best time to be an operator 47:02 - AI Summit preview: June 23-24, Freedom Factory, Beverly MA — build it live with Rachel 48:19 - The volume reality: someone using this system is posting 3x a day while you post twice a week ───────────────────────────── 🎁 FREE RESOURCES Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets #ShortTermRental #AIforSTR #STRSecrets #VacationRental #PropertyManagement #ContentStrategy #AirbnbInvesting #AIAgents #DirectBookings #STRScaling

    49 min
  4. "If You Don't Figure Out AI, Someone Else Will Take Your Bookings" | Hostaway CEO Marcus Räder

    May 18

    "If You Don't Figure Out AI, Someone Else Will Take Your Bookings" | Hostaway CEO Marcus Räder

    🔥 STR AI Summit — June 23-24 | Freedom Factory, Beverly, MA Only 100 seats. Built for operators who are serious about what comes next. 👉 strsecrets.com/aisummit If 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 did 02:01 - E & Chris reconnect — scaling conference takeaways + the Sardinia deal update 05:39 - Introducing Marcus Räder: building Hostaway into a $1B business 08:50 - 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 raise 14:03 - What it actually feels like to run a unicorn — the founder's relationship with time 16:20 - How to build a team that thinks years ahead when employees focus on today 17:34 - Why Marcus's best hires came from web hosting, not STR 19:37 - AI in STR: excited or worried? Marcus's honest take from the CEO seat 21:47 - The viral meme that perfectly exposes the DIY AI trap 22:45 - 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 cases 24:15 - How Hostaway built its AI control layer for guest communications 27:00 - Build in-house vs. stay third party: Marcus's framework for scaled operators 28:33 - The hidden danger of AI models that silently update and change answers 29:41 - The Uber lesson every STR operator needs to hear right now 31:25 - Will AI become a race to the bottom? Where monetization is heading 32:07 - The pool pump disruption: how AI reshapes maintenance costs and who profits 34:00 - "Findability" — go ask AI to find YOUR property right now and see what happens 35:15 - Why private equity is turning STR businesses into 10x assets with AI 36:18 - What the next decade of Hostaway looks like 38:33 - Direct bookings in 2026: the dead-simple strategy most operators still skip 39:26 - 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 booking 42:13 - Build big or go work for someone — Marcus's hard truth about entrepreneurship 43:13 - 100 marathons in 100 cities: the health journey and what flat feet taught him 47:07 - The calorie analogy that explains how small disciplines compound at scale 49:36 - 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-book STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets ───────────────────────────── #ShortTermRental #AirbnbInvesting #STRSecrets #VacationRental #PropertyManagement #STRScaling #AIforSTR #Hostaway #DirectBookings #RealEstateInvesting

    51 min
  5. I Spent $5,000 Learning AI the Hard Way — Here Are the 10 Mistakes You Don't Have to Make

    May 14

    I Spent $5,000 Learning AI the Hard Way — Here Are the 10 Mistakes You Don't Have to Make

    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

    53 min
4.7
out of 5
121 Ratings

About

The Short Term Rental Secrets Podcast is dedicated to providing actionable content to help new and seasoned real estate investors launch, automate and scale their Airbnb business and fast track their journey to financial freedom. You can enjoy the podcast and other free resources at www.STRsecrets.com

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