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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

Ep 272 – How AI Will Replace Most STR Ops Work (And What Operators Should Do) with Shahar Goldboim

2025-12-15T05:23:48-05:00

AI isn’t a tool anymore — it’s infrastructure. In this episode, Chris and E sit down with Shahar Goldboim, founder of BOOM, to break down how AI is fundamentally changing short-term rental operations, exits, and scale. From selling a property management company to building tech that replaces broken workflows, this conversation dives deep into why fragmented tools are failing and why operators who don’t adapt will fall behind. Inside this episode: Why “tech-enabled” STR businesses still fail The biggest mistakes operators make when exiting Why one company can’t do funds, PM, design, and tech well How AI eliminates 80% of guest [...]

Ep 272 – How AI Will Replace Most STR Ops Work (And What Operators Should Do) with Shahar Goldboim2025-12-15T05:23:48-05:00

Ep 248 – From Airbnb Suspension to 90% Occupancy with Midterm Rentals & AI Automation with Amanda Williams

2025-06-30T07:15:02-04:00

Amanda Williams branded herself as The Traveling Realtor and built a thriving rental business, only to be banned from Airbnb overnight. In this episode, she shares how that crushing moment forced her to pivot into midterm rentals, automate with AI, and rebuild a better business that runs with less stress, higher profits, and total platform independence. What You’ll Learn: Why Airbnb banned her (and what you can do to prevent it) How midterm rentals (MTR) gave her 90–95% occupancy The AI tool she built to automate listings, guest comms & content How she balances business with nervous system regulation & wellness [...]

Ep 248 – From Airbnb Suspension to 90% Occupancy with Midterm Rentals & AI Automation with Amanda Williams2025-06-30T07:15:02-04:00

Ep 247 – The Identity Shift That Unlocks Everything (And How to Use AI to Scale Smarter)

2025-06-23T06:36:29-04:00

Most people quietly self-sabotage… Not because they don’t want success. But because they still talk like the person who doesn’t have it yet. In this solo episode, Mike and E break down how internal dialogue shapes your future, and how AI can help you become the version of yourself that already wins. What you’ll learn: How to reprogram your self-talk to unlock growth Why “watering down” your vision is killing momentum The AI tools Mike uses weekly to review sales calls, write listings, automate ops, and even train his team How to use custom GPTs to build an internal consultant that [...]

Ep 247 – The Identity Shift That Unlocks Everything (And How to Use AI to Scale Smarter)2025-06-23T06:36:29-04:00

Ep 243 – From Zero to $1B: Hostaway CEO Marcus Rader on AI, Talent, and the Brutal Truth About Scaling

2025-06-09T06:32:25-04:00

In this raw, no-fluff episode, Hostaway CEO Marcus Rader shares the hard-won lessons behind building a billion-dollar vacation rental software company, starting with zero industry experience. Marcus breaks down: Why most entrepreneurs aim too small and why it costs them everything The mental and physical toll of building at scale (including 7 years without a dentist visit) How he filters “good money” vs “bad money” when raising capital The future of short-term rentals in a regulated, AI-powered world Practical leadership advice for scaling teams without losing your mission Plus: his marathon training, travel hacks, and how to avoid becoming a micromanaged [...]

Ep 243 – From Zero to $1B: Hostaway CEO Marcus Rader on AI, Talent, and the Brutal Truth About Scaling2025-06-09T06:32:25-04:00

Ep 242 – How AI & Leadership Are Scaling the Best STR Businesses in 2025

2025-05-20T05:28:04-04:00

This episode unpacks the real playbook behind scaling short-term rental businesses with AI, leadership, and culture.   Straight from the STR Boardroom event in Salem, hosts Chris and E break down their biggest takeaways from Dr. Rachel Gainsbrugh's AI workshop to the emotional breakthroughs in hot seats, to Mark from Minoan’s CEO mindset at 50+ employees.   What you’ll learn: • The AI stacking method Rachel used to double her sales team’s close rate • The 5 levels of VA hiring, from cheap help to AI-powered specialists • Why great team members outgrow companies, and how to lead through it • [...]

Ep 242 – How AI & Leadership Are Scaling the Best STR Businesses in 20252025-05-20T05:28:04-04:00

Ep 224 – AI to Automate Your STR Portfolio with Host Buddy Founders Jay Ullrich and Sam Mayes

2025-04-28T07:48:21-04:00

Looking to simplify your property management and maximize profits? In this episode, we explore AI tools that enhance guest experiences, optimize cleaning schedules, and improve booking conversions. Tune in and learn how to leverage AI for smarter, more efficient short-term rental operations! Jay Ulrich and Sam Mayes' Bio In 2021, co-founders Sam Mayes and Jay Ullrich began their journey in the short-term rental (STR) industry by establishing a management company in San Diego. Today, their team manages over 40 units, consistently delivering operational excellence and guest satisfaction. As the business expanded, one challenge became clear to almost every host they encountered: [...]

Ep 224 – AI to Automate Your STR Portfolio with Host Buddy Founders Jay Ullrich and Sam Mayes2025-04-28T07:48:21-04:00

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