AI isn’t the threat — it’s the opportunity most hosts are ignoring.



In this episode, we walk through how top operators are using AI and automation to scale smarter, simplify operations, and outpace the competition.

• How AI is transforming pricing, operations, and marketing

• The biggest mistake hosts make when “trying” automation

• Tools that save hours per week without losing the human touch

• Why your business model must evolve in 2025

• The new advantage: data-driven decision-making

Get the full AI Automation Playbook at strsecrets.com/ai

00:00:18 – Why AI Is the Next Big Shift in STR

00:02:12 – What Hosts Get Wrong About Automation

00:05:09 – The Tools Replacing Busywork in STR Operations

00:08:47 – How AI Enhances the Guest Experience

00:11:38 – Dynamic Pricing and Predictive Data in Action

00:15:22 – Building Systems That Learn While You Scale

00:19:10 – How to Combine AI With a Human Team

00:23:38 – Avoiding the “Set It and Forget It” Trap

00:27:41 – The STR Playbook for 2025 and Beyond

00:30:52 – Final Take: Use AI Before It Uses You

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

Your life is driven by one of two things: desire or fear.

In this episode, we break down how to stop making decisions from lack, step into an identity-led mindset, and actually create the conditions for growth.

• Desire vs. paradigm: the two voices in your head

• How to make decisions from faith, not fear

• The identity → behavior → reality chain

• Why discipline is just choosing desire repeatedly

• What to do when growth feels uncomfortable

• How your environment can hold you back

00:00:00 – Desire vs Fear: The Two Lenses

00:00:12 – Paradigm = Fear and Lack

00:01:44 – Choosing to Live From Desire

00:03:08 – The Identity → Behavior → Reality Flow

00:05:06 – Why Your Current Behavior Matches Your Identity

00:06:49 – Discipline = Making Desire-Based Decisions

00:08:05 – Asking: “Is This from Desire or Fear?”

00:10:12 – Growth Requires Discomfort

00:13:24 – Fear Speaks Louder Than Desire (At First)

00:16:22 – Growth Is Continuous If You Keep Choosing It

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

You can’t scale if you’re the cleaner, the guest texter, the bookkeeper, and the ops manager.

This episode breaks down exactly when to hire, who to hire first, how to onboard them, and how to keep them executing so you can grow your STR business instead of babysitting it.

• When it’s actually time to hire (not too early, not too late)

• Who your first hire should be in an STR business

• Sample VA schedule for guest communications

• How to onboard using SOPs instead of winging it

• What to pay and where to find VAs

• The weekly meeting rhythm that keeps them accountable

Want to Grab the Hiring and Onboarding Templates?

Just click the link below and DM us "VA".

Link: https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T031&utm_content=VA

00:00:04 – When to Hire Your First Person

00:00:29 – Signs You’re Doing a 40–60 Hour Week

00:03:52 – Operator First or Sales First?

00:10:07 – Sample STR VA Schedule (Guest Comms)

00:10:24 – What to Pay and What They Do

00:17:42 – Onboarding With SOPs, Not Vibes

00:17:52 – Weekly Meetings and Task Lists

00:18:56 – Growing Their Responsibilities Over Time

00:28:03 – Where to Find VAs

00:28:43 – Use Our Hiring & Onboarding Templates

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

You didn’t start an STR business to be a full-time cleaner, guest texter, or firefighter.

This episode breaks down how most hosts trap themselves in operations — and how to build systems that finally let you step out and scale up.

• Why “hustle” kills long-term growth

• The systems that keep your business running without you

• How to delegate without losing control

• Why buying back your time is your real ROI

• A blueprint to turn chaos into clarity

If you’re tired of putting out fires and want your STR to finally run smoothly,

go to strsecrets.com/ops

00:00:12 – Why Every STR Needs an Operating System

00:04:28 – Automating Guest and Team Communication

00:08:17 – Tracking Operations Like a Real Business

00:11:45 – How to Build Repeatable Systems That Scale

00:15:33 – Managing 100+ Units Without Losing Control

00:19:58 – Training Teams to Operate Like Owners

00:24:40 – Optimizing Listings for Efficiency and ROI

00:29:25 – The Data Metrics Every Operator Should Track

00:33:54 – Using Tech and SOPs to Eliminate Chaos

00:38:42 – The Future of STR Businesses Runs on Systems

Guest Bio:

Michael Dinwiddie is a real estate investor, Airbnb Superhost, and leader in hospitality operation who combines short-term rental management experience with a background in product marketing and customer experience design. As the founder of Togethere Vacation Rentals, Michael manages premium short-term rentals and boutique hotels across Washington State, helping owners increase profitability while creating meaningful guest experiences.

He also built Hospitality HQ, an operating system and training platform that equips hosts and managers with the tools, automations, and processes needed to scale efficiently. Michael’s work bridges the gap between hospitality and technology—bringing professional systems to help scale the next generation of short-term rental entrepreneurs.

Guest Link:

instagram.com/michael.dinwiddie/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

The latest Airbnb updates are already shaking the market.

From the new pricing structure to changes in visibility and payout logic, this episode breaks down what’s changed — and how hosts can respond before profits vanish.

We cover:

• Airbnb’s latest Q4 update and what it really means

• Why “Buy Now, Pay Later” hurts your revenue

• The 18% gap between guest and host payout

• How the algorithm update affects your bookings

• The steps to protect your listing performance right now

Want to track and protect your profits after the new Airbnb updates?

Just click the link below and DM us "AIRBNB" to get the exact spreadsheet Reilly shared.

https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T030&utm_content=AIRBNB

00:01:14 – The “Buy Now, Pay Later” Effect on Host Payouts

00:02:08 – Hidden Revenue Gaps in Airbnb’s Host Fee Changes

00:04:42 – What the Data Says About Visibility and Bookings

00:06:10 – How to Read and Use the Airbnb Spreadsheet

00:08:55 – Revenue Management Tips for the New Update

00:11:24 – Why Some Homeowners Will Lose More Than Others

00:14:58 – Understanding PM Revenue and Homeowner Splits

00:15:24 – Airbnb Host-Only Fee Changes Explained

00:16:01 – Channel Fee Split: How Airbnb Is Changing Payments

00:17:42 – The Real Fix: Adjusting Pricing to Protect Profit

00:19:33 – Why Transparency and Strategy Now Matter More Than Ever

00:21:14 – Recap: The Future of STR Hosting After These Updates

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

Airbnb just rolled out updates that change everything for hosts.

From hidden pricing shifts to the new “Buy Now, Pay Later” feature — this episode breaks down what’s happening behind the scenes and how it impacts your bottom line.

• Airbnb’s latest update — and what it really means for hosts

• The 18% pricing gap no one saw coming

• Why “Buy Now, Pay Later” could destroy your cash flow

• How to protect your listings from revenue loss

• The survival strategy hosts need for 2025

00:02:15 – The Buy Now, Pay Later Trap

00:04:50 – Why Airbnb’s Update Is Dangerous for Hosts

00:06:30 – How Guest Cancellations Can Bankrupt Your Month

00:10:22 – The Real Impact of Airbnb’s Policy Changes

00:14:18 – Protecting Your Listings With Better Pricing Strategy

00:18:45 – Revenue Management: How to Fight Back

00:23:10 – Why Market Compression Is Crippling Small Hosts

00:27:40 – The STR Survival Plan for 2025

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

Everyone wants a piece of the global STR market — but most will lose money doing it.

Fabio Moro reveals the brutal truths of running short-term rentals in Italy, and what it really takes to survive in a shifting STR landscape.

• Why most foreign investors get crushed in Italy

• The systems you must have to manage remotely

• What happens when the STR gold rush slows down

• How to protect your properties from market shifts

• Lessons from building a sustainable business, not a gamble

00:01:11 – How Fabio Started Investing in Italy From Abroad

00:03:45 – Finding and Trusting the Right Local Partners

00:06:20 – Turning Old Properties Into Luxury Short-Term Rentals

00:09:42 – Why Italy Is a Hidden Gem for STR Investing

00:12:55 – The Real Costs of Renovating in a Foreign Market

00:16:28 – Remote Management Systems That Actually Work

00:20:12 – Designing Guest Experiences That Command Higher Rates

00:23:40 – Due Diligence and Financial Discipline in STR Investing

00:28:10 – Scaling With Intent: Quality Over Quantity

00:32:02 – The End Goal: Freedom, Culture, and Sustainable Growth

Guest Bio:

Formerly a Partner at a major commodity trading firm with ventures spanning the US and Asia, Fabio now channels his international experience into developing distinctive villas and hospitality projects in Italy, guided by a vision of understated luxury, design and local authenticity

Guest Link:

casaroverella.it

palazzosanvito.it

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

Sief Khafagi didn’t just build a business—he built a standard.

In this episode, he reveals how leadership, culture, and vision turned TechVestor into one of the most respected brands in STR investing.

• How leadership shapes the future of the STR industry

• Building a culture that scales with integrity and precision

• Setting new standards for quality and operations

• Why great teams outperform any market cycle

• The mindset shift every STR leader needs to make

00:03:22 – The Real Problem: Bad Operators Drag the Industry Down

00:07:40 – Leadership and Vision: Believing Before Anyone Else Does

00:11:56 – Building High-Trust Teams That Scale

00:15:38 – Culture Over Everything: The Real Competitive Advantage

00:20:25 – Systems That Outlast the Founder

00:25:44 – The Truth About Scaling: Leadership vs. Management

00:30:57 – How TechVestor Blends Tech and Real Estate to Win

00:35:46 – The Future of STR Leadership and Industry Standards

00:40:38 – Legacy Leadership: Culture, Vision, and Setting the Bar Higher

Guest Bio:

Sief Khafagi is an ex-techie turned real estate investor who has helped thousands diversify into real estate. Today, he’s the founder of Techvestor, one of the first institutional-grade and backed STR portfolios. With their vertically integrated advantages across acquisitions, renovation, design, management, and more, Techvestor is the leader in short-term rentals as an asset class. Backed by in-house technology, one of the deepest talent benches in the industry, and most recently, institutional backing, they're on a path to 500+ owned STRs over the coming years.

Guest Link:

https://www.linkedin.com/in/siefkhafagi/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/