In this episode, Chris and E sit down with the founder of Vintory to uncover the real reason PMs fail, what the top managers are doing differently, and how to build a predictable machine for owner acquisition.

Whether you're starting with 5 doors or aiming for 500, Brooke breaks down the playbook that actually works.

Inside this episode:

• Why most PMs never break past 50–100 properties

• The REAL reason owner acquisition is so difficult

• Brooke’s formula for predictable PM growth

• Why marketing is now non-negotiable for property managers

• What the top PMs are doing differently

• How the industry is shifting — and where the opportunity is

00:02:11 – Brooke’s Story: How He Scaled to 500 Properties

00:06:34 – Why Most Property Managers Plateau at 50–100 Doors

00:09:58 – Owner Acquisition: The Hardest Part of PM Growth

00:13:22 – Why Homeowners Don’t Convert (And What They Really Want)

00:17:45 – The Data Behind Fast-Growing PM Companies

00:21:18 – Why Marketing Is No Longer Optional for PMs

00:25:40 – Building a Real Sales Pipeline for Property Management

00:30:12 – Brooke’s Predictable Growth Formula Explained

00:34:49 – Industry Shifts: Consolidation, Competition, and Opportunity

00:38:27 – The Future of PM Growth (And How to Win the Next Wave)

Guest Bio:

Brooke Pfautz is one of the industry's foremost experts in growing vacation rental inventory. He literally wrote the book on inventory growth – and it’s already a three-category Amazon bestseller. Brooke got his start in the industry in 2007 when he co-founded Vantage Resort Realty in Ocean City, MD, and took an idea on a napkin to more than 500 properties in just five years. After a successful exit, he went on to grow inventory for other major vacation rental brands as a Chief Business Development Officer in multiple destinations. Most recently, as an executive at a leading vacation rental software company, he saw first-hand through MasterMind groups that he launched and facilitated what worked and what didn’t for the 20 largest and most successful companies in the country. Today, Brooke leads Vintory, the first and only CRM & Sales and Marketing Automation Platform designed exclusively for Vacation Rental Managers to grow their inventory. At Vintory, a team of over 50 growth experts is laser-focused on one thing: helping VRMs hit or exceed their inventory growth goals.

Guest Link:

https://www.instagram.com/vintoryhq/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

Your STR business is worth more than you think—if you build it the right way.

In this episode, we break down the difference between operators who burn out… and operators who build real companies that survive, scale, and eventually sell for life-changing money.

We also cover the hard lessons from companies that grew too fast, collapsed, or went bankrupt—and how to avoid their mistakes.

In this episode you’ll learn:

• Why your STR business already has real enterprise value

• What happens if everything lives in your head (and how to fix it)

• The operational mistakes that bankrupted a fast-growing STR company

• How to build systems that survive without you

• What buyers REALLY look for in an STR business

• The path to a 7–8 figure STR exit

If you want help building an STR business that actually runs without you — and is worth something one day — click the link below:

https://go.strsecrets.com/podcast?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T033&utm_content=STRS

00:01:41 - Sonder going bankrupt

00:03:15 - talking about exits / long hold / vision

00:05:09 - private equity, Blackstone, KKR, etc.

00:06:47 - Vacasa, hyper-local focus, selling to PE

00:08:47 - SOP playbook, fear of death, what happens if you’re gone

00:10:20 - CEO role, brand, numbers, game plan

00:12:00 - not as easy as it looks, 70% with PMs 20+ units

00:13:19 - PE criteria, churn, “can somebody else run my business?”

00:14:55 - Built to Sell, books, contracts, “you not being the system”

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

The STR industry is shifting — and this episode marks the beginning of a new era.



Recorded LIVE inside the brand-new Freedom Factory, Mike, E., Chris, and Reilly break down the mindset, seasons, strategy, and direction that will define the next 5 years of short-term rentals… and your future in it.

• The story behind building the Freedom Factory

• Mike’s “origin moment” and how it shaped everything

• The dark seasons every entrepreneur must push through

• Why property management will create more millionaires than arbitrage

• The new PM roll-up and what it means for exits

• How STR Secrets is evolving with 3 new shows & deeper curriculum

00:01:41 – The Freedom Factory: How This All Started

00:04:52 – Mike’s Full Circle Moment at the Old Staples Desk

00:08:35 – The “Dark Seasons” of Entrepreneurship

00:12:48 – The Four Phases of Growth Every Operator Goes Through

00:16:55 – Chris’s Story: Going Broke to Buying His First STR

00:20:33 – Riley’s Risk: Payroll on a Credit Card & Buying His First Property

00:24:40 – The Identity Shift Needed to Enter Your Next Season

00:28:53 – Why Property Management Will Create More Millionaires

00:32:41 – The PM Roll-Up & Hotel Fund Vision

00:37:58 – The New Era of STR Secrets: Three Shows + Bigger Vision

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

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/