ai

Ep 315 – The Breezeway CEO Has Seen 350,000 Airbnbs. This Is the Mistake He Sees Everywhere | Jeremy Gall

2026-10-13T07:14:19-04:00

How do you grow a short term rental or Airbnb management business without losing the human touch that makes guests book in the first place? In this episode of the STR Secrets Podcast, Breezeway founder and CEO Jeremy Gall breaks down the real role of AI and automation in vacation rental operations, and why automating everything could quietly kill your business. Jeremy has spent 20 years building software for vacation rental operators. He founded FlipKey and grew it into one of the world's largest vacation rental platforms before TripAdvisor acquired it in 2013. Today he runs Breezeway, the AI powered property [...]

Ep 315 – The Breezeway CEO Has Seen 350,000 Airbnbs. This Is the Mistake He Sees Everywhere | Jeremy Gall2026-10-13T07:14:19-04:00

Ep 312 – The Only AI Masterclass Airbnb Hosts Need: Leads, Revenue, and Ad Spying on Autopilot

2026-09-21T06:50:28-04:00

🚨 The AI Summit is almost sold out — grab your ticket before it's gone: 👉 www.strsecrets.com/aisummit2 Sep 29 & 30 | Salem, MA | $497 | Less than 20 Seats Remaining Download the Ad Spying Skill and other resources mentioned in the training from here: In this AI masterclass, Ryan and Mike break down the 3 AI systems every short-term rental operator needs to grow their portfolio and maximize revenue — no VAs, no guesswork, just automation. What you'll learn: 🏠 AI Revenue Manager Connect Price Labs to Claude with one click and get a full portfolio revenue report in [...]

Ep 312 – The Only AI Masterclass Airbnb Hosts Need: Leads, Revenue, and Ad Spying on Autopilot2026-09-21T06:50:28-04:00

Ep 308 – From 0 to 40+ Properties & a Hotel That Pays for His Life | Alex Steeg

2026-08-24T06:22:43-04:00

If you want to run your STR business on autopilot by a bunch of AI agents then join us for a two day hands on Ai workshop on September 29-30. Register here: level.strsecrets.com/aisummit2 From one duplex to 40+ short-term rentals and a hotel that pays for his whole life — Alex Steeg proves you don't need a real estate background to build real wealth. In this episode, Mike and Mike sits down with Alex Steeg, co-founder of Shore Way Management. Alex and his wife Rachel started in 2018 with one property, zero experience, and a simple plan to "buy a duplex [...]

Ep 308 – From 0 to 40+ Properties & a Hotel That Pays for His Life | Alex Steeg2026-08-24T06:22:43-04:00

Ep 307 – The AI Tools Actually Making STR Operators Money in 2026 | Ryan Lefebvre

2026-08-17T09:31:10-04:00

Everyone is telling you to build AI tools. Ryan Lefebvre, the AI expert behind the tools at STR Secrets, is telling you to stop. In this episode, Ryan sits down with Mike Sjogren and Mike Reilly to explain why building your own AI is the new shiny object, and why it's quietly killing operators who should be focused on their business instead. Ryan is a former fraud analyst turned pilot turned STR operator who now builds AI systems for management companies. He shares which AI wins actually move the needle, and which ones are a total waste of your time. From [...]

Ep 307 – The AI Tools Actually Making STR Operators Money in 2026 | Ryan Lefebvre2026-08-17T09:31:10-04:00

Ep 302 – How to Onboard Airbnb Properties So Owners Never Leave (Full System)

2026-07-13T04:55:56-04:00

How do you onboard 7 vacation rental properties in one month without burning out your team? Mike Reilly breaks down the exact 6-stage onboarding system NC Stays uses for every new property, from the first homeowner call to the post-launch celebration. Homeowners' trust in property managers is at an all-time low. Nearly every owner has been burned before. The managers who onboard properties with a real system are locking in 5- to 10-year relationships and standing out in a market flooded with new co-hosts. In this training you'll learn the full checklist: the handoff call and 30 question onboarding form, the [...]

Ep 302 – How to Onboard Airbnb Properties So Owners Never Leave (Full System)2026-07-13T04:55:56-04:00

Ep 301 – Why the Next Few Years Are the Best Time to Build and Sell Your STR Business

2026-07-06T06:55:13-04:00

Something big is happening in short-term rentals, and most operators have no idea. In this episode, Mike Sjogren returns to the show with Mike Reilly. And they open with a trend that changes everything. In 2022, most short-term rentals in the US were run by hosts with fewer than 20 units. By 2025, that share had dropped hard. The reason is not that hosts quit. It is that private equity quietly started buying up management companies, because the margins are good and the industry is wide open. Mike breaks down what that means for you, and reveals the project STR Secrets [...]

Ep 301 – Why the Next Few Years Are the Best Time to Build and Sell Your STR Business2026-07-06T06:55:13-04:00

Ep 296 – Direct Bookings, AI Agents & Why Airbnb Fees Are Going to 20% | Mark Simpson Returns

2026-06-01T06:26:41-04:00

🔥 LAST CHANCE — STR AI SUMMIT, June 23-24 | Freedom Factory, Beverly, MA Only 100 seats. This is where direct bookings, AI agents, and the next decade of STR get built — live, with the operators leading the charge. 👉 strsecrets.com/aisummit ───────────────────────────── 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 [...]

Ep 296 – Direct Bookings, AI Agents & Why Airbnb Fees Are Going to 20% | Mark Simpson Returns2026-06-01T06:26:41-04:00

Ep 294 – $1B STR Company CEO Tells You Exactly How AI Will Eat Your Business (Or Make You Rich) | Marcus Räder, Hostaway

2026-05-18T06:13:44-04:00

🔥 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/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 [...]

Ep 294 – $1B STR Company CEO Tells You Exactly How AI Will Eat Your Business (Or Make You Rich) | Marcus Räder, Hostaway2026-05-18T06:13:44-04:00

Ep 293 – The Man Who Lost $50 Million and Called It a Seminar | Rod Khleif on Mindset, AI, and What’s Coming

2026-05-11T05:46:49-04:00

🎟️ 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 In 2006, Rod Khleif's net worth went up $17 million while he slept. Two years later, he lost $50 million. He didn't call it a failure. He called it an expensive seminar. In this episode, E sits down with Rod Khleif — Dutch immigrant turned multifamily mogul, bestselling author, and host of the largest commercial real estate podcast in the world. At 66 years old, with 30 companies built and over 300,000 student-owned multifamily units, Rod [...]

Ep 293 – The Man Who Lost $50 Million and Called It a Seminar | Rod Khleif on Mindset, AI, and What’s Coming2026-05-11T05:46:49-04:00

Ep 291 – The 4-Year Warning: Why AI is About to Replace Average Operators| David VanWert

2026-04-27T05:52:00-04:00

Most luxury STR owners write that electric bill every month without ever knowing what's causing it. David VanWert did the same thing — until he built a platform to fix it. In this episode, E and Chris sit down with David VanWert, founder of Umbra and owner of seven STR cabins in the Smoky Mountains and Mammoth Lakes. David built Umbra after spending years watching energy costs silently destroy the profitability of high-end vacation rentals — and after realizing no existing solution was built for the STR world. In this episode, David covers: - What Umbra does: smart power monitoring and [...]

Ep 291 – The 4-Year Warning: Why AI is About to Replace Average Operators| David VanWert2026-04-27T05:52:00-04:00

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