If you want to join our weekly free training:

https://www.facebook.com/groups/STRentalsecrets

Most property managers and co-hosts pitch homeowners on management fees.

Mike Reilly pitches them on $100,000 in tax savings. And it closes more deals than anything else.

In this Portfolio Clinic training, Mike breaks down the STR tax loophole — why it works, who qualifies, and exactly how to use it to attract high-income homeowners and win management contracts.

This is not investment or tax advice. But it is the most powerful conversation you can have with a prospective homeowner — and most co-hosts and property managers are never having it.

In this training Mike covers:

- Why taxes are the #1 expense for every high-income W2 earner and business owner

- How a doctor making $375K in California goes from a $145K tax bill to a $47K tax bill — with one STR

- What a cost segregation study is and how it accelerates depreciation in year one

- The two requirements to qualify for the STR loophole: 7-day average stay and 100+ hours of material participation

- Why 90% of CPAs don't know this loophole exists — and how to help your homeowner educate theirs

- The exact conversation flow to have with prospective and new homeowners

- How Mike charges a $20-25K consulting and design fee upfront — then takes over management in year two

- Real results: one homeowner got $80K back this year, another got $60K last year

- How to structure the deal so the homeowner qualifies AND you get the management contract

- What to do with a cost segregation study if the homeowner wants to be fully passive

- How to handle depreciation recapture and when to recommend a 1031 exchange

This is one of the highest-leverage strategies a co-host or property manager can learn right now.

Want help implementing this in your business?

Go to: https://strsecrets.com/implement

📲 Connect with STR Secrets:

Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

Apply to work with us: https://strsecrets.com/apply

STR Secrets Podcast: https://strsecrets.com/podcast

Timestamps:

0:00 - Why Taxes Are Your Homeowner's Biggest Expense

3:20 - The Math: How a Doctor Paying $145K in Taxes Can Change Everything With One STR

6:00 - What Is a Cost Segregation Study and Why Every Homeowner Needs One

8:30 - How Much Can You Depreciate in Year One? (The 25% Rule)

10:00 - The Two Tests to Qualify for the STR Loophole

12:00 - Running the Numbers: From $145K Tax Bill to $47K With One Property

14:30 - The Exact Conversation to Have With Every Prospective Homeowner

16:30 - How to Charge a Consulting Fee and Design Fee Upfront

18:00 - Real Results: $80K Back This Year, $60K Last Year

19:30 - What If the Homeowner Wants to Be Fully Passive?

21:00 - Depreciation Recapture and When to Recommend a 1031 Exchange

22:00 - Q&A: Cost Seg on an Existing Property, Passive Losses and More

Most couples don't survive a loss like that. Instead, it became the moment that changed everything.

In this episode, E and Chris sit down with Cara and Mark Truckey — two STR Secrets boardroom alumni who have built a real estate portfolio of 65+ units across Wisconsin and Florida while raising three kids and running multiple businesses.

This is one of the most honest and human conversations we have had on this show.

In this episode Cara and Mark cover:

- How losing their son reshaped their entire perspective on time, work, and money

- How Cara quit her hospital job in 2020 and Mark quit his plumbing W-2 in 2021

- How they went from a few house flips to 65+ rental units across two states

- Their first STR — a lake property in Wisconsin they bought by accident

- Why Mark struggled with delegation for years — and the 80/20 rule that broke the pattern

- How to find the right people for the right seats — and why belief in the vision matters more than skills

- How Cara transitioned into Savvy Realty as a top agent in the Tampa Clearwater market

- What actually keeps a husband and wife business partnership aligned

- The daily habit that is their real superpower — and has nothing to do with business

- How to change your identity before the results show up

- Mark's upcoming $130 million capital campaign for a K-12 school in Wisconsin

- Cara's goal: 40 STRs under management in Florida by end of 2027

- Their #1 secrets to success: courage and fighting past limiting beliefs

If you want to increase your revenue, automate your day to day operations and spend more time with your kids: http://strsecrets.com/apply

If you want to join our weekly free training:

https://www.facebook.com/groups/STRentalsecrets

Connect with Cara:

Instagram: www.instagram.com/caratruckey

Facebook: www.facebook.com/caratruckey

Savvy Realty: www.savvy.realty/cara

Timestamps:

0:00 - Highlights

1:00 - Introducing Cara and Mark Truckey

5:05 - Their Story: Growing Up in Wisconsin and Losing Their Son in 2016

7:32 - How Grief Changed Their Relationship With Time and Money

9:03 - How They Built the Portfolio: Flips, BRRRs and Their First Accidental STR

10:21 - How They Split the Business: Cara on Sales, Mark on Construction

11:56 - Building the Team: Florida and Wisconsin Operations

14:11 - Mark's Delegation Journey: The 80/20 Rule That Changed Everything

16:48 - Right People in the Right Seats: Why Belief in the Vision Matters Most

18:24 - Identity First: You Have to Become the Person Before the Results Show Up

21:33 - How to Actually Change Your Identity — Not Just Understand It

24:28 - Why Being Part of a Mastermind Has Always Been Their Edge

25:25 - Running a Business With Your Spouse — What Actually Works

26:47 - Spiritual Alignment: The Foundation That Kept Them Together Through Tragedy

27:23 - The Matthew McConaughey Analogy: You Won't Always Walk Side by Side

32:21 - How Cara Made the Decision to Join Savvy Realty

35:00 - Their Real Superpower: Health, Accountability and Alignment

38:27 - What's Next: Mark's $130M School Campaign and Cara's Management Goals

42:23 - Their #1 Secrets to STR Success

If you want to join our weekly free training:

https://www.facebook.com/groups/STRentalsecrets

Every time a past guest books your property again through Airbnb — Airbnb takes the fee. Again. Repeat guests generate over $1 billion in revenue for Airbnb annually. And most STR operators are doing nothing to capture that themselves.

In this Portfolio Clinic session, Mike Reilly breaks down the direct booking system he uses across his 30-property portfolio — and reviews a real direct booking website live with a community member.

He walks through how to collect guest info from every Airbnb and Vrbo stay, how to build a 12-touch text and email funnel that brings guests back without the OTA in the middle, and how to incentivize your team to close direct bookings on your behalf.

He also covers the occupancy tax process most operators get wrong, why your contact list is a business asset that increases your company's exit value, and what actually makes a direct booking website convert.

If you are still relying 80-100% on Airbnb for bookings — this is the training that changes that.

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 Airbnb Makes $1 Billion From Your Repeat Guests

2:27 - Why You Can't Build a Business on Someone Else's Land

4:36 - How Airbnb's Fee Change Impacted Revenue (And What to Do)

7:05 - Occupancy Tax: The Mistake That Could Cost You a Six-Figure Bill

9:23 - Live Website Review: Lori's Direct Booking Site

13:43 - What Makes a Direct Booking Website Actually Convert

19:53 - How to Collect Guest Info From Every Airbnb and Vrbo Stay

21:15 - The QR Code Exit Strategy That Drives Direct Bookings

21:35 - The 12-Touch Text and Email Funnel for Repeat Guests

24:34 - Why Mike Pays His Team $50 Per Direct Booking Closed

25:41 - Two Social Posts a Week — Done by Your Team, Not You

27:32 - How a 3,000-Contact CRM Protects You If Airbnb Shuts You Down

31:07 - Why Direct Bookings Increase Your Company's Exit Valuation

33:54 - Action Items and Closing Thoughts

If you want to join our weekly free training:

https://www.facebook.com/groups/STRentalsecrets

Most STR operators don't think about regulation until it's already too late.

Julie pulls back the curtain on what’s really happening in short-term rental regulation and why hosts can’t afford to stay invisible. From local politics to nationwide advocacy, this episode is a wake-up call for operators who think regulation is someone else’s problem.

Here's what we covered:

• How Julie went from accidental host to industry advocate

• Why anti-STR arguments often hide deeper community concerns

• The biggest mistake hosts make when regulations start changing

• Why advocacy is not charity, but a real business investment

• How small hosts can contribute without becoming full-time activists

• What the Right to Rent Collaborative is building for the future of the industry

Guest Bio:

Julie Marks is Executive Director of the Right to Rent Collaborative (R2RC), a national initiative supporting state and local short-term rental associations in building advocacy capacity, legal readiness, and sustainable funding infrastructure. An association founder and industry advocate, Julie works at the intersection of national strategy and local execution, helping communities organize and engage effectively with policymakers.

Julie founded the Vermont Short-Term Rental Alliance (VTSTRA) in 2021 and served on the Vacation Rental Management Association’s Government Affairs Council from 2022 to 2024. She operates Homestead Hospitality in Vermont and manages rental properties in Vermont and Washington.

Connect with Guest:

julie@r2rcollaborative.org

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

https://www.instagram.com/vtstra/

https://www.instagram.com/r2rcollaborative/

Timestamps:

0:00 - Intro

8:01 - Introducing Julie Marks

8:28 - How Julie Accidentally Became an STR Advocate

10:00 - From Op-Ed to Statewide Alliance: The Vermont Story

11:26 - Why the Same Fight Is Happening in Every Market

12:23 - What Communities Are Really Upset About (It's Not What You Think)

16:19 - The Hard Truth: What STRs Have Genuinely Changed

18:34 - Why "It Won't Happen in My Market" Is a Dangerous Assumption

21:16 - How to Get Involved Without Going to Every City Hall Meeting

23:35 - What the Right to Rent Collaborative Does and How It Works

26:17 - "I'm Too Small to Matter" — Julie's Response

28:21 - The $2 Per Booking Model: Your Business Insurance Policy

29:08 - Why This Is a Branding Opportunity, Not Just an Obligation

35:52 - How to Start a Local Association From Scratch

38:23 - Where to Find Julie and Get Connected

39:36 - Julie's #1 Secret to STR Success

If you want to join our weekly free training:

https://www.facebook.com/groups/STRentalsecrets

This one is different.

At our last STR acquisitions event at the Freedom Factory in Beverly, MA, we did something we'd never done before.

We filled a hat with real homeowner objections — things operators hear every day — and had four coaches handle them live on stage in front of 50 operators.

No prep. No script. No safety net.

Coaches Mike Reilly, Dave, Darryl, and E took turns handling objections like "your fees are too high," "you're not local," "I don't want to be locked in," and "I want to take advantage of the STR tax loophole." Each coach handled them differently — because that's the point. There is no single right answer. There's the answer that fits your voice.

This is an hour of live, unfiltered STR sales training recorded in the room. If you're growing a property management or cohosting business, this episode will change how you handle objections.

Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

If you want us to review your listing, org chart, pricing or anything related to STR business, join here:

➡ https://www.facebook.com/groups/STRentalsecrets

Most STR companies obsess over guest reviews.

Blue Gems obsesses over owner profitability.

And they grew to 180 properties under management doing it.

In this episode, recorded live at the Freedom Factory in Beverly, MA, E and Chris sits down with Aidan Groll — co-founder of Blue Gems Management, one of Florida's fastest-growing STR companies. Aidan and his partner JB manage 180+ properties across Orlando and Clearwater Beach with a 36-person team — and grew almost entirely through organic relationships, not paid ads.

In this episode Aidan breaks down:

- How he went from a corporate accounting job to buying his first duplex in March 2020

- How a 400 sq ft backyard ADU made $50K in its first year and convinced him to go all in on STRs

- Why Blue Gems puts owners 70% over guests — and how they pitch that to new clients

- Their full org chart at 180 units: 14 in maintenance, 7 in guest experience, 3 in sales and more

- Why they do ALL maintenance in-house — and why speed was the deciding factor

- How they automated 70% of guest communication with AI in the last year

- Their 7-day contract-to-live-listing goal and how they hit it consistently

- How they choose markets based on regulatory stability — not just cash flow

- Why they shut down their podcast and social media for 2+ years to focus on growth

- Their plan to reach 350-400 units through acquisitions of smaller operators

- The Valley of Disappointment — and why most people quit right before it gets good

- Aidan's #1 secret to STR success: patience

This is a masterclass in building a real, scalable STR management business.

---

About Aidan Groll:

Aidan Groll is the co-founder of Blue Gems Management, an Orlando-based vacation rental management company that has grown to oversee 180+ properties across Florida. Originally a real estate investor with a background in corporate accounting, Aidan and his business partner JB pivoted to short-term rentals in late 2021 — building their own management infrastructure before opening to third-party clients in early 2023. Since then, Blue Gems has scaled to a 36-person team with full in-house maintenance operations, serving property owners across Orlando and Clearwater Beach.

Time Stamps:

0:00 - intro

0:54 - Introducing Aidan Groll and Blue Gems Management

1:28 - What Blue Gems Does Differently (Owner-First Philosophy)

4:14 - The Real Cost of Building This Business

5:08 - Aidan's Origin Story: From Accounting Job to House Hacking in 2020

7:54 - The $50K ADU That Changed Everything

9:10 - Scaling to 180 Properties: How Blue Gems Grew Without Paid Ads

10:46 - The Contrarian Take: Why They Don't Chase 5-Star Reviews

13:46 - How to Pitch the Owner-First Model to New Clients

18:26 - Inside the Org Chart: 36 People, 180 Properties

20:08 - Why They Do All Maintenance In-House

25:38 - How AI Automated 70% of Guest Communication

29:54 - From Signed Contract to Live Listing in 7 Days

31:18 - How to Choose Markets Based on Regulatory Stability

36:49 - Why Aidan Is Selling His Portfolio to Bet on the Management Company

40:41 - The Real Cost of Building This Business

43:59 - The Future: 350+ Units and Acquiring Smaller Operators

47:15 - Aidan's #1 Secret to STR Success

Connect with Aidan:

Instagram: https://www.instagram.com/aidangroll/

LinkedIn: https://www.linkedin.com/in/aidan-groll

Email: aidan@bluegems.group

📲 Connect with STR Secrets:

Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

STR Secrets Podcast: https://strsecrets.com/podcast

If you want to increase your revenue, automate your day to day operations and spend more time with your kids: http://strsecrets.com/apply

If you want to join these live trainings:

https://www.facebook.com/groups/STRentalsecrets

This is the first episode of the STR Portfolio Clinic. A brand new series where me and Mike Sjogren pull up real STR listings on screen and diagnose what's working and what's not. Live. In front of everyone. No filter.

This episode is all about listings.

We reviewed two real Airbnb properties from operators who volunteered to put their listings on the hot seat.

First up is a brand new beach cottage in Oak Island, North Carolina. Second row from the ocean. Clean listing. But nobody's clicking on it. We broke down why and gave the owner a full game plan on the spot.

Then we pulled up a riverfront property in Murphy, North Carolina. Fly fishing right off the deck. Beautiful area. Went an entire summer with zero bookings. It took about 10 seconds to see what was wrong.

We also break down the ALE framework which stands for amenities, location, and experiences. This is the framework behind how we build listings across 30+ properties that generated over $5M in bookings last year.

If your listing has been sitting or your bookings have slowed down, this episode will show you exactly what to fix and in what order.

Want your listing or business reviewed on a future episode? Drop CLINIC in our DMs

TIMESTAMPS:

0:00 - What is the Portfolio Clinic

0:55 - The ALE Framework: Amenities, Location, Experiences

4:17 - Listing Review #1: Beach Cottage in Oak Island, NC

5:09 - Photo feedback: It's clean but it's too white

6:31 - How to use AI for sunset and lifestyle shots

7:15 - Staging amenities: Reilly's beach property example

8:41 - Who's your avatar and why it changes your photos

9:12 - Sjogren: The wizard room hero image strategy

10:33 - Using ChatGPT to create twilight shots

11:38 - Interior updates vs working with what you have

12:47 - Getting five star reviews on a new listing

13:52 - The combined listing strategy for side by side properties

16:58 - Aerial shot hack to show both properties

17:48 - Listing Review #2: Riverfront A-Frame in Murphy, NC

18:16 - Sjogren's first reaction: "I don't love this first photo"

19:04 - Andy's story: Zero bookings since launch

19:56 - Why you need to relaunch dead listings

20:35 - Phone photos are killing your listing

21:24 - What lifestyle photos this property actually needs

22:47 - Comp analysis: What top properties in Murphy look like

25:02 - Brutal feedback: The photos make it look dark and dated

26:35 - Staging the deck and outdoor space

28:41 - The game plan: Photos, relaunch, pricing, reviews

29:42 - The Airbnb new listing push and why Andy missed it

30:09 - Small changes that pay for themselves in one night

30:47 - Insurance and liability for offering amenities

33:23 - Bonus: Quick review of Christie's listing

35:40 - What's coming next and the Freedom Factory event

Most people end Q1 the same way they started it.

Behind on goals. Ahead on excuses.

In this solo episode, E breaks down why that happens — and what to actually do about it before Q2 starts.

This isn't a motivational pep talk.

It's a direct, honest look at the real reason you keep self-sabotaging — even when you know exactly what you need to do.

In this episode, E covers:

- Why the brain doesn't perceive time as time — and what that means for how you're living

- Tony Robbins' 3 S's framework: State → Story → Systems (and why you're skipping the first two)

- The 5 core wounds that create self-sabotage: rejection, abandonment, humiliation, betrayal, and injustice

- The difference between being self-centered vs. self-aware — and why it changes everything

- The belief thermostat: why you always reduce yourself back to what you think you're worth

- 3 questions to ask yourself right now as you close out Q1

- The one question E asks himself that "terrifies the shit out of him" — and keeps him moving

If the year hasn't gone the way you planned — this episode is the reset you need.

📲 Connect with STR Secrets:

Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

Apply to work with us: https://strsecrets.com/apply

STR Secrets Podcast: https://strsecrets.com/podcast

Timestamps:

0:00 - Intro

2:09 - Q1 Check-In: Are You Still Holding Your Standards?

3:57 - Why Time Feels Like It's Running Away (The Science of Memory Markers)

6:13 - Stop Just Learning — Start Experimenting

7:13 - Tony Robbins' 3 S's: State, Story, and Systems

9:23 - Why Mindset Work Alone Keeps Failing You

9:47 - The 5 Core Wounds Behind Every Self-Sabotage Pattern

11:23 - How Your Brain's 3 Layers Are Keeping You Stuck

13:38 - Self-Centered vs. Self-Aware: The Shift That Changes Everything

15:37 - The Belief Thermostat: Why You Keep Reducing Yourself

17:05 - Your Honest Q1 Review: Facts Only, No Stories

18:38 - 3 Questions to Ask Yourself Before Q2 Starts

20:33 - Nobody Is Coming to Save You

22:56 - "Is This the Final Version of You?"

Check out our free 6 step course: https://level.strsecrets.com/pc-book

If you want to join these live trainings:

https://www.facebook.com/groups/STRentalsecrets

If your listings aren't getting booked right now — don't panic and drop your prices.

In this week's Thursday training, Mike Reilly sits down with Maryann Wahhab, revenue management expert and STR operator across 6 states, to break down exactly what's working right now to get booked at the rates you want.

Maryann went from college basketball coach to full-time STR revenue manager — and now helps operators stop leaving money on the table in soft markets.

In this episode, Mike and Maryann cover:

- Why your slow bookings are probably a listing problem — not a pricing problem

- The booking window zones every operator needs to understand (and how to price each one)

- How Mike went 30% up year over year on Vrbo with one simple OTA trick

- The "booking velocity" metric Maryann tracks at 7, 15, and 30-day marks

- How a listing went from page 6 to page 2 on Airbnb in one week

- Why virtual stays are a game changer for dead listings

- The full listing re-optimization playbook for properties with no bookings in 30+ days

- How to use Airbnb's rule sets and length-of-stay discounts to capture more revenue in slow season

This is the training your listings need right now.

---

🎙️ About Maryann Wahhab:

Maryann is a revenue management expert and STR operator managing properties across 6 states. A former Division I basketball coach, she left the game in 2023 to manage properties full-time — and now helps STR operators maximize revenue in any market condition.

---

Timecodes:

0:00 - Why Your Listings Aren't Getting Booked Right Now

2:30 - Meet Maryann Wahhab: From Basketball Coach to STR Expert

6:00 - How to Read Your Market Before You Touch Your Prices

10:00 - Booking Window Zones Explained (And How to Price Each One)

15:30 - Booking Velocity: The Metric That Tells You When to Act

20:00 - How to Play the Airbnb and Vrbo Algorithm Game

25:30 - The OTA Trick That Got Mike 30% Up Year Over Year on Vrbo

30:00 - Virtual Stays and How to Reinvigorate a Dead Listing

36:00 - The Full Re-Optimization Playbook for Struggling Listings

41:30 - Length-of-Stay Discounts and Airbnb Rule Sets in Slow Season

46:00 - How to Differentiate Your Listing So You're Never in a Price War

Instagram: https://www.instagram.com/sean_bakhtiari/

Check out Seacoast 2 Summit: https://www.seacoast2summit.com

Check out our free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

What happens when a corporate finance guy from Boston decides he's done working for someone else — and bets on short-term rentals?

Sean Bakhtiari is the co-founder of Seacoast 2 Summit Vacation Rentals and The Bakhtiari Group, a top-performing real estate sales team across Massachusetts, New Hampshire, and Maine. As an active STR investor, his work sits at the intersection of real estate, hospitality, and investment strategy throughout New England.

After 9 years in Boston's financial district, Sean bought his first STR. Then a second. Then started building a management company.

At 12 properties, he hit a wall. He was good at business development and client relationships. But systems, operations, and scale? Not his strengths. That's when a serendipitous call from Chris changed everything.

Today, Sean and Chris co-run Seacoast to Summit Vacation Rentals — managing 120+ properties across the New Hampshire seacoast, lakes and mountains region, and North Shore of Massachusetts. Almost entirely on referrals, with virtually no paid marketing.

In this episode, Sean and Chris pull back the curtain on:

- How they identified each other as the right partner (and what 3 things you need to align on before you sign anything)

- Sean's "help first, never sell" philosophy — and why it's responsible for most of their growth

- Why they've said no to 10+ deals in the last 3 months (and why that's the right call)

- The two fears they stay up at night thinking about as they scale

- How to delegate without feeling like you're losing control

- What it takes to keep your team culture intact as you grow

- Why boutique hotels might be the next frontier for this business

This is a rare episode — a founder bringing on his business partner and pulling off the veil on how a real, values-driven STR company actually works at scale.

---

Timestamps:

0:00 - Introducing Sean Bakhtiari: Chris's Business Partner

2:45 - How Sean Went From Corporate Finance to STR Management

6:30 - Building Seacoast to Summit: From 12 to 120 Properties

10:15 - How Sean and Chris Found Each Other (The Serendipitous Call)

15:00 - The 3 Things You Must Align On Before Partnering

18:30 - The "Help First" Sales Mindset That Built the Business

23:00 - Why They Said No to 10 Deals in 3 Months

27:00 - The Two Fears They Have About Growing Too Fast

32:30 - How to Delegate Without Losing Control

37:00 - Keeping Team Culture Intact at Scale

42:00 - What the Future Looks Like: Boutique Hotels and Brand Building

46:00 - Sean's #1 Secret to STR Success

Instagram: @jeremiahkwatson

Business: www.affluentvacays.com

Check out our free 6 step course: https://level.strsecrets.com/pc-book

STR Secrets FB group https://www.facebook.com/groups/STRentalsecrets

He did everything people told him to do.

Got clean. Went to college. Got a good job. Made good money.

And he was still unhappy.

In this episode, we talk with Jeremiah Watson. Jeremiah just quit his corporate job. He now runs an 18-property cohosting business in Los Angeles. He is the 73rd person to leave their job through STR Secrets.

Here's what you'll learn:

→ How Jeremiah went from addiction and jail to building a real business

→ Why he lost $50K his first year — and what he changed

→ How he got his first cohosting deal with one cold call

→ The small team that runs his business today

→ His goal: 66 properties by the end of 2026

This is what actually doing the work looks like.

Timestamps:

00:00 - Who Is Jeremiah Watson?

03:12 - From Addiction and Jail to Turning His Life Around

08:11 - Why He Chased the Corporate Dream

11:36 - He Tried STRs and Lost $50K in Year One

13:16 - How He Found Cohosting and Got His First Deal

16:36 - How He Grew From 1 to 18 Properties

19:11 - His Team and How the Business Runs Today

21:27 - His Big Goal: 66 Properties by End of 2026

22:45 - What to Do If You Have a Job and No Time

27:06 - How to Balance Drive With Gratitude

31:57 - Why This Business Is About More Than Money

It’s about building the team that can support the growth.

In this episode, Chris and E sit down with Alex Hall — talent advisor and leadership strategist — to break down the real challenges STR operators face when building teams.

From job clarity and org structure to burnout, hiring, and leadership development, Alex shares the frameworks that help operators scale from a handful of listings to a real company.

If you're trying to grow beyond the stage where you do everything yourself, this episode is a masterclass in leadership and people management.

Inside this episode:

• Why most STR companies don’t actually know who reports to who

• The biggest hiring mistake operators make while scaling

• How to structure a team from 10 to 100+ listings

• Why burnout happens during fast growth

• The leadership habits that retain great talent

• When to introduce equity or long-term incentives

If you want a real business — not just a portfolio of properties — it starts with leadership.

Guest Bio:

Alex Hall is the founder of Valinor Talent Solutions, where he serves as a fractional HR executive helping growing companies build strong people strategies, leadership development, and scalable teams. With over a decade of experience in talent and organizational development, he partners with businesses to create high-performing workplaces. Alex works with short-term rentals to develop their talent strategy so they can focus on delivering exceptional guest experiences through thoughtful design, strong systems, and hospitality-driven service.

Guest Contacts:

alex@valinortalent.com

www.valinortalent.com

Get FREE Access to our 6 STEP course:

https://www.strsecrets.com/podcast

Timestamps:

00:00 – Why Most Teams Don’t Know Their Role

02:00 – Success, Identity, and Leadership Growth

04:30 – Introducing Alex Hall: Talent Advisor for STR Operators

07:25 – When STR Businesses Actually Need HR Support

09:20 – The 3 Levels of Team Structure as You Scale

12:40 – The Most Common Hiring Problems in STR Companies

14:00 – Why Job Clarity and Accountability Are Missing

17:10 – The 33% Rule: When Leaders Outgrow Their Team

20:05 – Burnout Signals Every Operator Should Watch

23:20 – Building Org Structures for 10–100 Listings

26:00 – Why Systems Matter More Than Org Charts

27:00 – How Great Leaders Reward and Motivate Teams

30:00 – Equity vs Performance Bonuses for Key Employees

33:00 – The 3 Rules of Leadership: Clear, Kind, Respectful

36:10 – Leadership Lessons for First-Time Founders

39:50 – AI’s Role in Future STR Operations

42:40 – Final Advice for Building a Great STR Team

Instagram ➡️ https://www.instagram.com/mikereillync/

Follow this link for the Free training:

https://level.strsecrets.com/pc-book

You want to grow a property management business, you will eventually hit the same wall:

You become the person slowing things down.

In this video, I share the exact playbook we built before hiring our first salesperson.

Inside this training you’ll learn:

• The perfect type of property we target

• The exact type of homeowner we want to work with

• The biggest problems Airbnb owners face today

• How we show our value to sign new clients

• The "UI Method" for finding struggling Airbnb properties

• The exact numbers and goals we set for our sales team

• The best ways we find and talk to new owners

• Our step-by-step sales process and first phone calls

• What happens right after an owner signs with us

If you want to grow your company to 30, 40, or 50+ properties, you need a sales plan that works every single time.

This episode shows you exactly how we built ours.

Subscribe for new weekly videos ➡️ https://bit.ly/2Nrn4XO

Timestamps:

00:00 – Why You Need a Sales Plan

01:12 – The 4 Steps of Our Sales Playbook

02:10 – Finding the Perfect Property

03:05 – The Perfect Homeowner

04:18 – Problems Airbnb Owners Face

05:45 – Creating a Strong Offer

07:00 – Why You Need a CRM Software

08:50 – Sales Goals and Numbers to Track

10:20 – The Experiment: 120 Calls in 6 Weeks

11:35 – Our Sales Win Rates

12:18 – How to Find Leads: The UI Method

13:30 – Using Referrals and Partners

14:05 – Direct Mail and Ads

15:05 – Running Facebook Ads for Leads

16:10 – Our Sales Process

17:20 – The First Call and Asking Questions

18:15 – Handling Owner Concerns

19:05 – Bringing on a New Owner

20:00 – Weekly Sales Tracking

21:10 – Hiring and Testing a Salesperson

Connect with us on other social media platforms:

STR Secrets FB group ➡️ https://www.facebook.com/groups/STRentalsecrets

Michael Sjogren FB Page ➡️ https://www.facebook.com/theAirbnbGuy

Instagram ➡️ https://www.instagram.com/miike.sjogren

Linkedin ➡️ https://www.linkedin.com/in/mikesjogren

Then 2008 hit.

Reserves drained.

Assets liquidated.

Eventually — bankruptcy.

Most investors never come back from that.

In this episode, Jon St. Leger breaks down:

• What the 2008 crash really felt like

• Why he keeps his portfolio at 33% LTV

• How to prepare for the next recession

• What “Equity Manifestation” actually means

• How he turned a 20-room motel into a 47-key boutique hotel

• Why delayed gratification builds real wealth

• The blue-collar advantage most people ignore

Jon now owns 13+ short-term rentals, long-term rentals, and is breaking ground on a beachfront boutique hotel in the Outer Banks.

If you’re serious about building generational wealth in real estate — this one is different.

Follow Jon on Instagram: @jon_boy14

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

TimeStamps:

00:00 – Equity Manifestation & The $100M Vision

02:00 – Identity, Mindset & Future Self Thinking

05:30 – From Blue Collar Beginnings to Construction Company

09:45 – Building a Portfolio… Then 2008 Hit

12:30 – The Mental Toll of Bankruptcy

14:45 – Lessons From the Crash: Reserves & Exit Strategies

17:00 – Why He Keeps 33% Loan-to-Value

19:00 – Not Overleveraging in Growth Cycles

21:30 – From STR Portfolio to Boutique Hotel Developer

24:00 – Turning a 20-Room Motel into 47 Keys

27:00 – Getting Town Buy-In & Emotional Attachment

30:00 – Leading Teams & Maintaining Morale

32:30 – The Power of Delayed Gratification

35:00 – Return on Sweat Equity (R.O.S.E.)

37:00 – Blue Collar Wealth Strategy

39:00 – The $100M Real Estate Target

41:00 – Where Opportunity Lives & Final Advice

Supply is rising.

Middle-class travel is tightening.

Occupancy is projected to decline.

Rates are compressing.

If your Airbnb still looks like 2024… you're in trouble.

In this training, I break down my full 4-step photography system:

– What to upgrade BEFORE hiring a photographer

– How to properly interview lifestyle photographers

– What to do on photo day to maximize impact

– How we use AI to write captions and enhance photos

– How we organize everything inside our operating system

If you’re scaling a property management or co-hosting business, this is not optional anymore.

Timestamps:

00:00 – Why 2026 Will Be Harder for STR Operators

02:12 – Supply Is Rising, Occupancy Is Falling (The Reality Check)

03:30 – Step 1: Refresh Before You Photograph

06:10 – Using ROI Analysis to Justify Property Upgrades

09:20 – Real Estate vs Lifestyle Photography (Huge Difference)

12:05 – What Elite STR Photos Actually Look Like

16:00 – How to Properly Interview a Photographer

19:10 – Photo Day Execution: Staging That Converts

22:15 – Organizing Photos for Scalable Operations

25:00 – Using AI to Write Captions for Every Photo

27:00 – Editing & Enhancing Photos with AI

29:15 – The Freedom Operating System Explained

32:00 – How to Scale Photography Across Multiple Listings

34:15 – Mastermind, CRM, and 2026 Growth Strategy

36:50 – Final Advice: Upgrade or Get Left Behind

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

They don’t.

In this Boardroom recap from the Freedom Factory, we unpack the real reasons businesses stall — and it’s not systems.

It’s people, identity, and the state you operate from.

Inside this episode:

• Why most business bottlenecks are solved by the right “who”

• The difference between hiring people and developing talent

• W2 vs 1099 mistakes operators make

• Why State → Story → Strategy is the real order of success

• The 4 archetypes running your decisions (Warrior, Magician, Lover, Sovereign)

• Why high performers get stuck in Warrior mode

• How seasonality applies to your business and your life

• Why kindness to yourself is a competitive advantage

If you feel like something is holding you back… this episode will hit.

Timestamps:

00:00 – Boardroom at the Freedom Factory Recap

02:15 – From Cooked Books to 80,000 Meals a Week

04:10 – Visionaries Get Small When Stuck in Operations

05:45 – The “Right Who” Solves Most Bottlenecks

07:50 – Building Talent Structure (Not Just Hiring)

10:40 – W2 vs 1099: What Operators Must Understand

12:20 – The 3 S’s of Breakthrough: State > Story > Strategy

15:05 – The 4 Archetypes Running Your Life

18:30 – Warrior Mode & The Seasonality of Growth

21:10 – Kindness, Presence & The Power of Awareness

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, she breaks down how she pivoted during the pandemic, why most investors don’t have enough grit, and how mastering calendar discipline can completely transform your rental income.

We dive into:

• Why community changes everything in real estate

• The biggest mistake STR hosts make when pivoting to midterm rentals

• Calendar discipline and how to control guest behavior

• How to use data tools like PriceLabs the right way

• Building multiple income streams without burning out

• Protecting your time while scaling a real estate business

If you’ve been feeling stuck, burned out, or uncertain about the next step in your rental business — this episode will challenge you to think differently.

Timecodes:

00:00 – Intro

03:12 – Why Community Is a Competitive Advantage

05:00 – The Power of Grit in Business

07:02 – Vivian’s Real Estate Journey (2004–2018 Gap Explained)

09:56 – Corporate Burnout at Apple & Transferable Skills

13:05 – Why Most Investors Pivot Too Fast

16:48 – Why Midterm Rentals Make More Strategic Sense

21:41 – The Calendar Discipline Most Hosts Ignore

25:31 – Transitioning from STR to MTR the Smart Way

30:29 – Why Vivian Built Her Own Platform

35:07 – Building Teams Without Burning Out

38:10 – Setting Boundaries & Protecting Your Time

42:05 – The 80% Confidence Rule (Just Do It)

Guest Bio:

Vivian Yip started investing in 2004 but took her journey more seriously after being inspired by a hotel owner she met at a random airport encounter in Chicago. She and her husband started to flip houses in 2018 and ended up making enough to afford to keep the real estate. She always dreamed of leaving the corporate world, so she used her steady paycheck at Apple to support their real estate goals. In 2019, she started her first short-term rental and was forced to pivot in 2020 with the pandemic. Now she runs multiple businesses focused on short-term rentals, mid-term rentals, and corporate housing, and she coaches others on the strategy behind securing profitable leases from Airbnb and beyond.

Guest Link:

Instagram.com/vivianyip_official

vivian@vivianyip.com

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, Madison Rifkin breaks down what actually works when partnering with content creators, why follower count is a useless metric, and how STR operators should think about social media as a long-term control channel — not a quick ROI play.

We also go deeper into founder identity, building brands that can be sold, and the mistakes operators make when they tie everything to themselves.

If you want more direct bookings, stronger brand trust, and a business that isn’t dependent on Airbnb alone, this episode is required listening.

Inside the episode:

• Why follower count doesn’t matter anymore

• How to vet influencers the right way

• The real way to think about ROI from content creators

• Why social media is your only true control channel

• Content ideas that work even without a “viral” property

• Founder identity mistakes that kill exits

• How to build a brand that survives without you

Timestamps:

00:00 – Why Influencer Marketing Is Broken for Most STR Hosts

03:20 – Madison’s Journey Building Mount and Entering STRs

06:40 – Why Follower Count Is a Terrible Metric

10:10 – How to Vet Influencers Based on Brand Alignment

13:30 – The Truth About ROI in Influencer Marketing

17:10 – Why Social Media Is a Control Channel, Not an Ad

20:00 – Content That Works Without a “Viral” Property

23:10 – Founder Identity and Why It Hurts Exits

26:30 – Building a Brand That Isn’t Tied to You

30:45 – Lessons From Selling a Company and Starting the Next Chapter

Guest Bio:

Madison Rifkin is the Founder and CEO of Mount where she finds the world's best hidden gems. She connects STR hosts and local businesses to local influencers and travel content creators so travelers can discover these hidden gems. She’s rooted in the Short Term Rental Industry where she’s won the Rising Star Award in 2022 and 2023.

Guest links:

https://www.linkedin.com/in/madison-rifkin-23037712a/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, we sit down with Hayley Anderson, a 22-year-old operator already on her second business, to unpack the mindset, discipline, and leadership traits that actually drive growth. From failing early to building confidence through reps, this conversation goes far beyond arbitrage or co-hosting.

If you want to scale your business — or your life — this episode will challenge how you think about comfort, confidence, and commitment.

Inside the episode:

• Why conviction matters more than experience

• How confidence is built through reps and failure

• The leadership habit that quietly builds culture

• Why comfort is the enemy of growth

• Learning to bet on yourself before results show up

• Applying mindset across business, relationships, and life

Timestamps:

00:00 – Intro

04:20 – Hayley’s Early Hustle and Second Business at 22

08:10 – Confidence Is Built Through Reps, Not Motivation

12:30 – Failing Early Without Letting It Define You

16:40 – Comfort vs Growth: The Tradeoff Most Avoid

20:15 – Leadership Starts With Small Cultural Habits

24:35 – Betting on Yourself Before Results Show Up

29:00 – Applying Mindset Across Business and Life

33:40 – Why Age, Model, and Capital Matter Less Than Belief

38:10 – The One Trait That Predicts Long-Term Success

Guest Bio:

Hailie Maarie Anderson is a 22 year old short term rental host operating over 70 rentals across three markets, all run 100% remotely through a blend of technology and teams.

While scaling her own portfolio, she has taken the stage at industry events to share her systems and insights, and has successfully coached over 1,300 individuals to start and scale their own short term rental businesses. Hailie’s mission is to be a leading voice for those who want to build and live an unconventional life, one without limits!

Guest Link:

https://www.instagram.com/hailiemaarie/?hl=en

https://www.tiktok.com/@hailiemaarie

https://youtube.com/@hailiemaarie?si=3qCgG6OPXqwZTgU2

https://www.linkedin.com/in/hailie-maarie-4b20a5276/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, we break down AirDNA’s 2026 outlook and translate the data into real, tactical decisions for hosts and property managers. Demand is softening, supply is shifting, and average properties are losing ground — but operators who adapt will win.

This is a data-backed walkthrough of what’s changing, why it matters, and exactly what to do next.

If you want the Training on how you should look at increasing your pricing so that you are not making 15 to 18% less than you were a year over year just click the link and DM "FEE".

https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T035&utm_content=FEE

Inside this episode:

• What AirDNA’s 2026 data actually says about demand and supply

• Why average properties will lose occupancy and revenue

• The markets and property types positioned to outperform

• How to talk homeowners into smart upgrades (with ROI)

• Why property managers are pulling ahead of solo hosts

• Using AI and systems to protect reviews and prevent burnout

00:00 – What the 2026 STR Outlook Means for Hosts & Property Managers

03:30 – Why STR Supply Has Flattened (And Why That Matters)

06:10 – Demand Is Softening: The Economic Reality Hosts Must Accept

09:15 – Average Properties Will Lose Occupancy in 2026

12:00 – Why Larger, Luxury Properties Are Winning Again

15:00 – Shedding Low-Performing Properties to Refocus Growth

18:20 – Coastal & Urban Markets: Where Smart Money Is Moving

21:00 – How to Sell Homeowners on Strategic Property Upgrades

24:30 – Property Managers vs Solo Hosts: The Performance Gap

27:40 – AI, Systems, and the Only Way to Scale Without Burning Out

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, we break down what actually changes when you go from being a solo operator to leading a real team. From earning respect instead of demanding it, to building systems that support people (not suffocate them), this conversation unpacks the leadership shifts required to scale without chaos.

If you’re growing doors, people, or partnerships — this episode will change how you think about leadership.

Inside the episode:

• The two ways leaders earn respect (and why only one works)

• Why supporting team members’ goals makes you more valuable

• How ego quietly slows down growth

• Leading teams through systems, not micromanagement

• What it really takes to earn buy-in as a leader

• Why consistency beats motivation when scaling

00:00 – The Two Ways Leaders Show Up (Title vs Example)

04:10 – Why Supporting Team Growth Makes You More Valuable

08:05 – From Solo Operator to Leading People

12:30 – Letting Go of Ego to Scale Faster

16:05 – Earning Respect Without Authority

20:10 – Using Systems to Reduce Team Burnout

24:05 – Aligning Company Goals With Personal Goals

28:00 – Consistency Over Motivation in Leadership

32:10 – Scaling Teams Without Losing Culture

36:20 – The Leadership Standard That Sustains Long-Term Growth

Guest Bio:

Ryan Leake, originally from Mill Valley, CA, moved to Austin, TX in 2023, where he left corporate America and founded Host Del Casa, a short-term rental management company.

After successfully building the business, Host Del Casa merged with Five Star Vacation Home Rentals (FSVHR), where Ryan now serves as a Managing Partner for the #1 luxury short-term rental management company in Central Texas - managing 60+ luxury short-term rental properties across Austin and San Antonio.

In addition to his role at FSVHR, Ryan became a coach and consultant for STR Secrets, the leading short-term rental business coaching program, where he helped operators overcome self-limiting beliefs and build profitable, lifestyle-driven STR businesses.

Today, Ryan continues to coach and mentor new short-term rental operators, share insights as a thought leader in the space, and prioritize a life designed around freedom, impact, and balance.

Guest Link:

www.instagram.com/itsaleake

ryan-leake.com

fivestarvhr.com

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, Frank Bosi (Hostfully) joins the show to unpack the real challenges STR leaders face as they scale—pressure, decision fatigue, emotional weight, and the constant tension between automation and hospitality.

Drawing from years inside luxury hotels like Ritz-Carlton and Four Seasons, Frank breaks down what most operators get wrong about tech stacks, leadership, hiring, and guest experience—and how to build systems that create confidence instead of doubt.

Inside this episode:

1. Why tech stack decisions are emotional, not logical
2. How disconnected tools quietly create leadership stress
3. The difference between automating tasks vs removing hospitality
4. What luxury hotels get right about training and consistency
5. Why leaders must absorb pressure instead of passing it down
6. How to hire people who protect your brand when you’re not watching

This is a must-listen for any STR operator building a team, scaling systems, or feeling the weight of leadership.

00:01 – Why Tech Stack Decisions Are Emotional, Not Logical

03:45 – Automation vs Hospitality: Where Operators Go Too Far

07:10 – The Weight of Leadership Most People Aren’t Ready For

11:00 – Why Disconnected Tools Create Doubt and Stress

15:20 – Lessons STR Operators Can Steal From Luxury Hotels

19:10 – Why Leaders Can’t Have “Bad Days” Publicly

23:30 – Hiring People Who Protect Your Brand When You’re Not There

27:40 – Training, Standards, and Why Consistency Beats Luxury

31:50 – Using Tech to Create Confidence, Not Complexity

36:40 – The Real Role of a Leader in Scaling STR Operations

Guest Bio:

Frank Bosi is the Senior Director of Partnerships at Hostfully, a leading platform supporting short-term rental operators around the world. He drives strategic relationships across the STR ecosystem; working with technology partners, influencers, coaches & thought leaders to help property managers scale and deliver great guest experiences.

Frank also actively contributes to industry conversations through webinars, events and podcasts (such as this) designed to help operators grow smarter, faster, and more profitably.

Outside of work, Frank prioritizes faith, fitness, and family; spending his free time with his wife and kids, training CrossFit, and staying focused on overall wellbeing.

Guest Link:

https://www.instagram.com/frank_bosi/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, E and Chris break down why most people start the year motivated… then quietly drift back into old patterns. The problem isn’t strategy, tools, or ambition — it’s misalignment between who you say you want to become and how you actually spend your time.

This conversation dives deep into identity, courage, time audits, consistency, and the hidden habits that either compound your growth or quietly sabotage it.

Inside this episode:

1. Why your calendar tells the truth about your real priorities
2. The “perfect week” exercise that exposes misalignment fast
3. Why every new level requires letting go of your old identity
4. How fear, comfort, and ego silently slow your progress
5. The power of small, consistent actions over big intentions
6. Why courage often means saying “no,” not “yes”

If you’ve ever felt busy but stuck — this episode will hit home.

00:00 – Why New Year Motivation Dies Faster Than You Expect

02:05 – The Reality Check: When Goals Collide With Real Life

04:20 – The Calendar Test: Do Your Actions Match Your Goals?

07:40 – Designing Your “Perfect Week” (And What It Exposes)

10:55 – Your Dreams Are Expensive — Here’s the True Cost

14:30 – Killing the Old Version of Yourself to Level Up

17:55 – Faith vs Fear: Making Decisions Without Freezing

21:30 – Small Habits That Quietly Compound Massive Change

25:10 – Letting Go of Ego to Create Space for Growth

29:05 – Enjoyment, Consistency, and Becoming Your Best Self

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, we break down what actually separates top-performing short-term rentals from the ones stuck in the middle. From design and amenities to operations, leadership, and systems—this is a real look at how elite STR businesses are built and sustained in hyper-competitive markets.

This isn’t theory. It’s what’s working right now.

Inside this episode:

- Why “good enough” STRs are getting crushed

- The amenity arms race (and how to win without wasting money)

- What guests notice that most hosts completely miss

- How ops and hospitality matter more than design long-term

- Why disciplined systems protect profit—even in down years

- The leadership mindset required to scale without chaos

If you want longevity in this industry, this episode is required listening.

00:06:15 – Becoming “The Guy” in a Hyper-Competitive STR Market

07:45 – Why Copying Competitors Is a Losing Strategy

09:15 – The New Minimum Standard for STR Design & Amenities

11:40 – Why Half-Upgraded Properties Always Underperform

18:50 – The Amenity Arms Race: What Actually Moves Revenue

20:00 – When Design Stops Mattering and Ops Take Over

26:10 – Building Teams and Systems That Don’t Break Under Stress

30:45 – Leadership Lessons from Military and STR Operations

34:05 – How Efficiency Protects Profit in Down Revenue Years

39:35 – The Long-Term STR Play: Scale, Discipline, and Longevity

Guest Bio:

Shane O’Connor is the CEO & Founder of Alchemy Real Estate & Alchemy Hosting. Alchemy is based in Tampa, FL, building a portfolio of Short-Term Rental assets primarily focused in Central Florida. By delivering vertically integrated, top-tier service from beginning to end in the investment process, Alchemy has grown from a single property (and single employee) to 11 properties & a team of four in less than a year. In that same time, Alchemy will have also delivered more than $3M in closed real estate deals for its clients.

By the end of 2022, it is Shane’s goal to have a blended Direct Ownership & Co Hosting portfolio of 30 properties centered in Florida, to then begin expanding to other markets. Shane is a graduate of the United States Naval Academy and served as an Officer in the U.S. Navy for 9 years. He received an M.S. Degree in Real Estate from the University of Florida. He runs the company with his brother, Captain Devin O’Connor, who is an active duty Marine Corps helicopter pilot in addition to being the Director of Operations for Alchemy.

Guest Link:

https://www.instagram.com/oc_dreams19/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, Chris and E break down why goals alone don’t create change, how identity drives momentum, and the real reason most people stall out by February. This is a deep, practical conversation on discipline, accountability, emotionalized goals, and how to build habits that actually stick.

If you’ve ever felt stuck despite “doing all the right things,” this episode will reframe how you think about growth — personally and professionally.

Inside this episode:

• Why identity matters more than motivation

• How emotionalized goals create automatic discipline

• The “never two days in a row” rule that builds momentum

• Why most people sabotage themselves without realizing it

• How to design accountability that actually works

• Turning small daily actions into long-term transformation

👉 If this episode resonated, share it with someone who’s setting big goals this year — and subscribe for more real conversations on growth, leadership, and execution.

00:00 – Why the Point of a Goal Is Growth, Not the Outcome

02:05 – Identity vs Outcomes: The Real Way to Set Goals

04:20 – Emotionalizing Goals to Create Immediate Action

06:10 – Going Deeper on “Why” Using the Seven Layers Exercise

08:35 – Shifting from “I Have To” to “I Get To”

10:15 – Building Momentum with Small, Non-Sexy Wins

12:40 – Vision First: Thinking Big Enough for the Next Level

15:05 – Quarterly Sprints and the Power of the 12-Week Year

17:40 – Time Blocking Life, Family, and Business (In That Order)

20:30 – Accountability, Never Missing Twice, and Staying in Motion

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, Stacey St. John breaks down how self-awareness, intuition, mindset, and values-driven leadership shape long-term success in business and life. From recognizing limiting beliefs to building aligned teams and managing energy, this conversation goes far beyond surface-level motivation.

If you’ve ever felt stuck, overwhelmed, or pulled in too many directions — this episode explains why and what to do about it.

Inside this conversation:

1. How intuition and body awareness guide better decisions
2. Why identity drives action (and keeps people stuck)
3. The difference between excitement and misalignment
4. How to hire and lead based on values, not resumes
5. Practical mindset tools to reset stress and overwhelm
6. Why self-image and internal stories affect performance
7. How high performers accept feedback without ego

00:00 – Why Most Entrepreneurs Stay Stuck (It’s Not Strategy)

03:45 – Introducing Stacey & Why Mindset Drives Everything

07:20 – Front Pocket vs Back Pocket Decisions Explained

10:50 – Learning to Trust Intuition Without Second-Guessing

14:30 – Energy, Stress, and Showing Up as a Leader on Bad Days

18:10 – Building the Right Team: Values Over Skills

22:40 – Why Misaligned Hires Quietly Kill Momentum

27:05 – Identity Shifts Required to Reach the Next Level

31:20 – Rewriting Internal Stories That Limit Growth

35:50 – Integrating Mindset Work Into Daily Business Life

Guest Bio:

Stacey St. John is a visionary real estate entrepreneur who is reshaping the short-term rental industry for women on Airbnb. She founded the Female Short-Term Rental Investors Facebook Group, The STR Sisterhood, and The Short-Term Rental Virtual Summit for Women. Stacey began her short-term rental journey on Airbnb in 2020; she quickly realized the industry’s potential and the opportunity to empower women through real estate investing to help them create successful, profitable “Airbnb businesses.” She has since built a 7-figure portfolio and left her corporate career to focus on her mission. Stacey is a strong advocate for women in business and is committed to creating a more equitable and inclusive industry. She is a frequent speaker at short-term rental and Airbnb industry events and is a regular contributor to industry publications.

Guest Link:

https://www.instagram.com/stacey_st.john/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

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 communication (without killing hospitality)
• Why fragmented STR software stacks are breaking ops
• How AI becomes the new infrastructure for scale

00:00 – Why Solving Everything Breaks Most Tech-Enabled STR Companies

03:05 – “Business as a Service” vs Traditional STR Software Stacks

06:20 – From Operator to Platform Builder: Shahar’s Real Estate Path

10:10 – Why Tech-Enabled PMs Fail Without Focus

14:30 – The Hidden Cost of Fragmented PMS + Tools

18:05 – Why AI Fails Without Full Operational Data

22:40 – How AI Can Eliminate 80% of Guest Communication

27:15 – The Real Bottleneck: Scaling Ops, Not Software

32:10 – Why All-in-One STR Platforms Are the Future

38:20 – The Direction of AI, Automation, and STR Businesses

Guest Bio:

Shahar Goldboim is the Co-Founder and CEO of Boom, the world’s first Autonomous Property Management System (AiPMS)—a platform redefining how real estate assets are operated through AI. Before founding Boom, he built DesignedVR, a hospitality management company overseeing more than $150 million in assets. This extensive experience gave him a firsthand understanding of the intricate, day-to-day challenges property operators face.

Throughout his career, Goldboim has been involved in hundreds of millions of dollars in real estate transactions as an investor and broker, and has deployed over $50 million in syndication funds. That deep operational and financial experience shaped his belief that the future of property management lies in automation, intelligence, and human-centered design.

Today, Boom merges hospitality, real estate, and AI to help operators around the world manage smarter, scale faster, and unlock the full potential of their assets.

Guest Link:

https://www.linkedin.com/in/shahar-goldboim-80820b95?utm_source=share&utm_campaign=share_via&utm_content=profile&utm_medium=ios_app

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, Chris and E sit down with Mark Lumpkin from STR Cribs, the company behind 500+ STR setups, to break down the real reasons properties fail and what the best operators do differently.

If you’re buying, designing, furnishing, or managing STRs — this is a masterclass in thinking like a pro instead of an amateur.

Inside this episode:

• The biggest mistakes investors make when buying or furnishing STRs

• Why “more amenities” isn’t the answer — strategic amenities are

• How to work with (and filter out) bad owners

• The 80/20 rule for projects, clients, and portfolio performance

• Why elite STR teams operate like “SEAL Team 6”

• How culture, tension, and standards lead to scale

• The future of STR Cribs and Mark’s next business moves

Guest Bio:

Mark Lumpkin helps investors set up highly profitable STRs all over the country.

00:00 – How STR Cribs Started & Grew to 500+ Setups

00:04:45 – Why High-Net-Worth Investors Still Make Rookie Mistakes

00:09:10 – The Amenities Strategy That Actually Drives Bookings

00:13:55 – Institutional Investors vs Mom-and-Pop Operators

00:18:25 – The Problem With Owners Who Want to “Test It First”

00:22:40 – The 80/20 Rule, Pumpkin Planning & Firing Bad Clients

00:27:05 – Sniper vs Machine Gun: How to Focus Your Time as an Operator

00:31:30 – The STR Cribs Hiring Philosophy: SEAL Team 6

00:36:15 – Creating a High-Performance Culture Through Healthy Tension

00:41:50 – What’s Next for STR Cribs & Mark’s Personal Vision

Guest Link:

https://www.linkedin.com/in/mark-lumpkin-84b173142/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, Bernie Cesareo reveals the mindset and identity shifts that transformed his life, his confidence, and his STR businesses — from shrinking portfolios to scaling multiple companies with clarity and purpose.

This episode breaks down the real reason most hosts stay stuck, how to think and act like a CEO, and the inner work required to grow a business that matches the life you want.

Inside this episode:

• The identity upgrade that changed Bernie’s life

• How self-image controls your STR results

• Why talking about your vision attracts the right people

• The shift from operator → leader → CEO

• How Bernie built multiple businesses by delegating

• Why gratitude, belief, and clarity fuel massive growth

00:01:12 – Bernie’s Big Mindset Shift: Stop Doing Everything Yourself

00:04:07 – “Assume the Wish Fulfilled”: Rewriting Your Identity

00:08:10 – Manifesting the Dream Jeep: Breaking 30 Years of Beliefs

00:11:20 – Running Multiple STR Businesses Through Identity Upgrades

00:14:36 – Lifestyle Freedom: Why Bernie Never Misses His Son’s Games

00:17:00 – The Elder-Care Village Vision: Thinking Bigger Than STR

00:20:12 – From Player to Coach to CEO: Letting Go of Control

00:24:18 – Correcting Systems, Not People: Real Leadership

00:28:55 – How Speaking Your Vision Attracts the Right Opportunities

00:33:42 – Gratitude, Belief, and the Identity That Builds Your Future

Guest Bio:

Bernie Cesareo and his wife Courtney started the company by turning a long-term rental in their hometown into a short-term rental and doing everything themselves from guest support to cleaning and maintenance. Happily surprised with the success and popularity of this property, they decided to turn this side hustle into a primary business. They loved providing quality accommodations and creating great value for their guests and felt they could do this on a larger scale. They started growing the business by becoming co-hosts for other property owners and have added team members to help make everything run smoothly. After several years, they have a team of 8 that manages anywhere from 20-40 properties.

Guest Link:

https://eaglestays.com/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

With Sonder filing bankruptcy and operators across the country getting crushed by fixed leases, the truth is clear: the STR model you choose determines whether you scale… or sink.

In this episode, we break down why arbitrage is failing, what Sonder’s collapse teaches every host, and why co-hosting remains the most profitable, low-risk, scalable model in 2025 and beyond.

Inside this episode:

 • Why arbitrage collapses under pressure

 • The hidden costs operators never calculate

 • Why co-hosting produces higher margins with lower risk

 • How boutique operators beat centralized “big brand” models

 • What the fastest-growing hosts are doing differently

 • The shift every STR operator must make in 2025

Message me to get a free resource and see how the program could fit your goals.

Click the link below:

https://go.strsecrets.com/podcast?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T034&utm_content=RESOURCE

00:01:00 – The Real Cost of Arbitrage: Leases, Debt & Cash Burn

00:02:30 – Why Arbitrage Margins Collapse in Today’s Market

00:03:45 – Co-Hosting vs. Arbitrage: The Risk Difference

00:05:10 – Arbitrage at Scale Becomes a Cash-Flow Death Trap

00:06:15 – Real Examples of Small Operators Losing Money

00:07:10 – The Tiny Margin of Error That Kills Arbitrage Deals

00:08:30 – Why Co-Hosting Wins: Low CAC, High Lifetime Value

00:10:20 – How Operators Are Scaling Co-Hosting With $0 Spend

00:12:20 – Centralized vs. Local: Why Guest Experience Matters

00:15:00 – Why Arbitrage Can’t Keep Up With Industry Changes

00:17:00 – The Bankruptcy Wave: Small Operators Getting Hit

00:18:30 – How to Pivot Out of Arbitrage Before It’s Too Late

00:20:10 – What a Healthy Co-Hosting/PM Business Looks Like

00:22:00 – No Get-Rich-Quick: The Reality of STR Success

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

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/

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/



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/



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/

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/

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/

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/

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/

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/

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/

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/

In this breakdown, we show you exactly how to rebuild your listing from the ground up to rank higher, convert faster, and stand out in a crowded market.

• The step-by-step to create a perfect, profit-ready listing

• The mistakes 90% of hosts make in titles and descriptions

• How to fix your visuals and brand in minutes

• What data says about click-through and conversions

• The system top hosts use to stay booked year-round

Want to make your Listing Perfect? Grab the FREE Guide.

Click the link below and DM us "OPTIMIZE"

https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T029&utm_content=OPTIMIZE

00:00:56 – Creating the Perfect Listing: What Goes Into It

00:03:39 – The Listing Description Framework (Step-by-Step)

00:05:34 – Lifestyle Photos That Drive Bookings

00:09:16 – Photo Strategy: Location, Amenities, Experience

00:13:24 – Use Captions to Boost Click-Through Rate

00:14:24 – The Big Description Mistake: Paragraphs vs Bullets

00:21:44 – Are You Actually Optimized? The Search-to-Listing Check

00:24:03 – KPIs to Optimize Your Listing (Property Refresh Cadence)

00:25:30 – Test Photos for Higher Conversions & CTR

00:26:57 – Build Your Direct-Booking Brand (After You Dominate Airbnb)

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

In this episode, Thibault shares actionable strategies that hosts can use to protect margins, win more bookings, and scale smarter.

• Why Airbnb’s new fee model has hosts freaking out

• How to price for what guests see (not what you keep)

• Tools like PriceLabs—and why they’re useless without context

• How European vs. U.S. guests think about fees differently

• When to simplify pricing and present “one clean price”

• The principles of occupancy, demand, and market alignment

00:05:12 – 3 Pricing Foundations Every Host Must Know

00:07:02 – Why Hosts Are Freaking Out About Airbnb Fees

00:08:22 – The Real Reason Airbnb Changed Its Fees

00:09:15 – The Only Price That Matters to Guests

00:10:24 – Why “One Clean Price” Converts Better

00:11:50 – Airbnb vs. Vrbo vs. Booking.com Costs Compared

00:12:09 – How Airbnb Went From Host-Friendly to Guest-First

00:24:50 – Are More Bookings Always Better?

00:25:04 – AI + Pricing Strategy: Where the Future Is Headed

00:25:22 – Who Owns Mistakes—You or the Machine?

Guest Bio:

Thibault Masson is the Head of Product Marketing at PriceLabs. His short-term rental journey started as a villa owner in Bali and St. Barts, which gave him firsthand insight into the opportunities and challenges of hosting. That passion for hospitality later brought him to Booking.com, where he worked on vacation rental strategy at a global scale, and inspired him to launch Rental Scale-Up as a platform for industry knowledge-sharing. Today at PriceLabs, Thibault brings together his experience as a host, tech marketer, and industry advocate to help property managers worldwide grow through smarter pricing and revenue management.

Guest Link:

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

Get FREE Access to our Community and Weekly Trainings:

http://group.strsecrets.com/

• How to pitch revenue expectations with confidence

• The $10K guarantee that beat out competitors

• Proposal + deal analyzer templates revealed

• How to handle homeowners on the phone

• Closing tactics to avoid being ghosted

• The 13-day timeline broken down step by step

Want the ACTUAL Step by Step Training? Just click the link below.

https://go.strsecrets.com/watch-strs-vacasa?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T028&utm_content=StepByStep2

In this episode, Matt shares his hard-earned lessons on revenue management, scaling, and the mindset shifts that set top operators apart.

• The truth about revenue management: when to DIY vs. hire

• How beginners can scale from 1–2 units to many

• Success traits Matt has seen across hundreds of operators

• Why your calendar is the foundation of business success

• The mindset shift: “If you can’t help yourself, you can’t help others”

• How to design life first, then build STR around it

00:02 – DIY Revenue Management: Matt’s 3 Best Tips

14:11 – Success Traits vs. Failure Traits

15:29 – The Power of a Strong WHY

18:29 – Calendar & Life Buckets for STR Success

19:08 – If You Can’t Help Yourself, You Can’t Help Others

20:52 – Designing Life First, Then Business

Guest Bio:

Matthew McDonald is a short-term rentals and hotels investor and coach.

Guest Link:

matt.mcdonald@strsecrets.com

Get FREE Access to our Community and Weekly Trainings:

http://group.strsecrets.com/

In this episode, finance expert Ben Coons breaks down the numbers behind gross vs. net commission models—and what you must do to protect your margins.

• Gross vs. net commission explained in plain English

• How Airbnb’s fee hits managers vs. homeowners

• Why this change is different from Vrbo and Booking.com

• Pricing adjustments to avoid eating the new fee

• Commission stacking and where your money really goes

• How to communicate fee changes to homeowners clearly

• Key takeaways to stay profitable under the new system

Co-hosts and homeowners: want the real numbers on Airbnb’s 15% fee?

Click the link and DM us “SPREADSHEET” and we’ll send you the file.

Link: https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T027&utm_content=Spreadsheet

00:04:30 – Example Scenarios: Who Really Pays the Fee

00:07:00 – Comparing Airbnb, Vrbo, and Booking.com

00:11:30 – Impact on Gross Model Operators

00:14:00 – Impact on Net Model Operators

00:18:30 – The Homeowner’s Point of View

00:23:30 – Commission Stacking: The Hidden Cost

00:26:00 – Pricing Adjustments to Stay Profitable

00:29:00 – How to Communicate Fee Changes to Homeowners

00:32:00 – Key Takeaways: Run the Numbers & Adapt Early

Get FREE Access to our Community and Weekly Trainings:

http://group.strsecrets.com/

In this episode, Chris shares practical frameworks and timeless principles that every business owner (and STR host) can use to stand out, attract clients, and scale smarter.

• Why marketing and sales matter more than ever

• The real difference between content and community

• How to build a personal brand the right way

• Authentic content vs. performative posting

• Head vs. heart: the two frames of content

• Why information ≠ transformation in business

• How to message to your avatar’s pain + desire

• Funnels, ads, and what they can’t replace

• Systems for managing leads without overwhelm

• Why investing in belief shifts your identity

00:01:27 – Why Listen to Chris (Marketing & Sales Depth)

00:03:07 – Community Leverage > Content Alone

00:11:38 – “Give Me a Framework” Moment

00:12:02 – Starting a Brand the Right Way

00:15:05 – Content Resistance, Authenticity, and Output

00:16:48 – Frames of Content: Head vs. Heart

00:21:26 – Information ≠ Transformation

00:26:33 – Avatar, Pain + Desire (Messaging 101)

00:28:15 – Ads, Funnels, and Social Avoidance

00:34:45 – Investing in Belief and Identity Shift

Get FREE Access to our Community and Weekly Trainings:

http://group.strsecrets.com/

In this episode, we break down the cohosting model step by step—from the basics to the systems that let you scale sustainably.

• What cohosting really is (and how it works)

• The 3 key things you need before starting

• How to choose the right market for success

• Proven ways to find clients and grow your portfolio

• The cohost funnel: your roadmap from startup to scale-up

Want the tested and proven Pitch Deck? Just click the link below and DM us "Pitchdeck"

https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T026&utm_content=Pitchdeck

00:04:45 – What Is Cohosting

00:11:49 – Cohosting vs. Arbitrage

00:12:59 – Why Arbitrage Is Failing

00:15:45 – Why Cohosting Is a Better Model

00:17:26 – Three Key Things Before Starting

00:23:40 – Market Selection for STR

00:26:52 – Acquisition Channels for Clients

00:28:15 – The Cohost Funnel Framework

00:29:40 – Tracking Where You Are in the Funnel

00:34:10 – Special Giveaway for Listeners

Get FREE Access to our Community and Weekly Trainings:

http://group.strsecrets.com/

In this episode, Emanuele and Mike break down how STR can fuel bigger goals, lasting freedom, and a life by design.

• Why STR is a tool, not the destination

• The mindset shift that changes how you build

• How to keep your bigger vision in focus

• Avoiding the trap of chasing unit count

• Using business to buy back your time and freedom

00:03:21 – Designing a Business That Lasts

00:05:26 – Keeping Your Bigger Vision Alive

00:06:32 – The Mindset Shift for STR Success

00:11:00 – The Mindset Shift for STR Success

00:12:15 – Why Belief Fuels Momentum

00:15:27 – Designing a Business That Lasts

00:17:11 – Designing a Business That Lasts

00:19:35 – How to Build Lasting Momentum

00:20:25 – Designing a Business That Lasts

00:20:56 – Scaling With the Right Mindset

Get FREE Access to our Community and Weekly Trainings:

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In this episode, he joins Emanuele to break down the science behind choosing the right markets and making STR numbers work for you.

• How John analyzed 100+ STR markets with zero failures

• The method he uses to “decipher the numbers”

• Why market selection is the real make-or-break skill

• Common mistakes hosts make when running numbers

• How to use data to build a sustainable STR portfolio

00:04:20 – Using Data to Drive STR Success

00:07:23 – Using Data to Drive STR Success

00:08:38 – How to Analyze STR Markets Effectively

00:09:33 – Using Data to Drive STR Success

00:10:45 – How to Analyze STR Markets Effectively

00:19:15 – Learning From Costly STR Mistakes

00:19:53 – Spotting Profitable STR Deals

00:21:15 – How to Analyze STR Markets Effectively

00:22:57 – How to Analyze STR Markets Effectively

00:25:27 – Using Data to Drive STR Success

Guest Bio:

John Bianchi is the Founder of STR Search. He has successfully directed over $100M+ investments into cash-flowing Airbnbs across the country. As a master of deciphering complex datasets, John has a 100% success rate across 250 + properties for helping his clients acquire cash-flowing Airbnbs. When he's not poring over data, he’s spending quality time with his family.

Guest Link:

https://www.instagram.com/theairbnbdataguy/

Get FREE Access to our Community and Weekly Trainings:

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This episode dives into how that moment reshaped his approach to business—and why building systems that outlast you is the true measure of success.

• The turning point when Steve realized he couldn’t keep grinding

• Why time freedom matters more than unit count

• How to design an STR business that runs without you

• Systems vs. hustle: the real key to longevity

• Lessons every host should apply before burnout hits

00:06:06 – Why Time Freedom Beats Unit Count

00:08:03 – The Health Crisis That Sparked Change

00:11:22 – Reframing Success Around Freedom

00:14:48 – Designing a Business That Runs Without You

00:16:52 – Shifting From Hustle to Sustainability

00:20:08 – Systems That Keep Growing Without You

00:26:32 – Avoiding the Burnout Trap

00:29:10 – Lessons From Scaling the Wrong Way

00:33:49 – Time Freedom as the Real Metric

00:34:20 – Building an STR Business That Lasts

Guest Bio:

Steve Resnick left the corporate world to pursue a career in co-hosting. He scaled from 12 to 99 properties in less than 2 years.

Guest Link:

https://linktr.ee/heavenlyrez

Get FREE Access to our Community and Weekly Trainings:

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This episode dives deep into mindset, grit, and the obstacles that stop most people before they ever scale.

• The difference between interest and commitment

• Why obstacles are often just excuses in disguise

• Lessons from Navy SEALs on resilience

• How to reframe challenges into momentum

• What separates consistent winners from quitters

👉 Do you really want it? Prove it—click the link below and start building your STR business today.

https://go.strsecrets.com/podcast?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T025&utm_content=Wantit

00:00:02 – Deciding If You Really Want It

00:01:29 – The First Mindset Shift Toward Success

00:02:24 – Breaking Through Excuses and Rationalizations

00:03:26 – Why Most People Quit Too Early

00:04:50 – Building Grit When Challenges Stack Up

00:06:01 – Turning Pain Into Long-Term Discipline

00:07:15 – Lessons on Focus From Elite Performers

00:08:29 – How to Push Past Mental Barriers

00:09:39 – Recommitting When Doubt Creeps In

00:10:58 – Keys to Sustainable Personal and Business Growth

Get FREE Access to our Community and Weekly Trainings:

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But the ones that work? They’re powered by more than numbers.

In this episode, we break down both sides of the equation: finding deals that actually perform and delivering hospitality that scales profit.

• 10-point hospitality playbook

• Why 95% of STR deals never make sense on paper

• The creative edge investors need to make deals work

• Why service ≠ hospitality (and why guests feel the difference)

• How to balance ROI with guest delight and repeat bookings

00:03:56 – Service vs. Hospitality

00:06:11 – Setting Higher Financial Targets

00:08:09 – Guest Experience at Every Stay

00:15:12 – Building a Hospitality-Driven Team

00:16:23 – Guest-Centric Business Model

00:17:17 – Scaling Means Scaling Leadership

00:20:27 – The Roots of Modern Hospitality

00:22:52 – Designing Emotional Guest Checkpoints

Get FREE Access to our Community and Weekly Trainings:

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In this episode, they share the systems, deals, and mindset that made it possible.

• How they pivoted from co-living to STRs

• The growth path from a handful of units to 80

• Systems they rely on to keep operations tight

• The partnerships that accelerated their scale

• Lessons learned about market selection and timing

00:04:31 - Learning from a high-functioning real estate company

00:05:52 - Landing a management gig through direct outreach

00:08:04 - Managing a growing number of people

00:10:15 - Staying focused while running STR operations

00:14:42 - Biggest drags on a short-term rental business

00:16:05 - What each founder values most in the business

00:18:59 - Identifying problems and fixing them

00:20:48 - Preventing issues from stacking up

00:23:39 - Taking responsibility for team mistakes

00:26:57 - Boutique hotel as a pivotal business asset

00:28:39 - Balancing investment strategy with STR management

00:34:36 - Staying at your own properties to evaluate quality

00:37:18 - Challenges get easier with experience

Guest Bio:

Blake Anthony Carter and Jeremy Courtney have both been operating in real estate and property management for over a decade. They initially got started in the co-living space, which led them to short-term rentals. They eventually sold our co-living business and with all-in on short-term rentals. Blake and Jeremy started a Facebook group and a meet-up group that allowed them to become known as the go-to guys for STRs in Austin. Their company is called Cribs. Blake and Jeremy now own a boutique hotel and three SF doors. They manage over 80 listings and have a real estate sales/consultant team.

Guest Link:

https://www.instagram.com/blake.anthony.carter

https://www.instagram.com/thejeremycourtney

Get FREE Access to our Community and Weekly Trainings:

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In this episode, we dive into what it takes to scale, the operational demands behind success, and how to grow without sacrificing your life.

• How the top U.S. property manager was built since 2021

 • The workload reality behind rapid STR growth

 • Why work-life balance is elusive in property management

 • How to keep guest satisfaction high while scaling

 • Lessons on building a sustainable management model

Want to get crystal clear on your goals and scale your STR business?

Click the link below to book a discovery call and see if our Mastermind is the right fit for you.

Link: https://go.strsecrets.com/podcast?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T024&utm_content=Goal

00:00:43 - Guest Introduction: Jamie Lane on the Report

00:04:58 - Operational Quality: Maintaining Cleaning at Scale

00:05:53 - Local PM Groups vs. National Lists

00:08:26 - Threshold: ~20 Listings Per Market To Appear

00:10:28 - Work Ethic Analogy (Kobe at 3:00am)

00:12:56 - Hiring/Team/Tech Stack

00:15:28 - Value Score Signal vs. Outcome

00:16:37 - Seasonality or Demand Shifts

00:19:48 - Methodology: Econometric Models to Isolate Drivers

00:22:04 - Pricing Tactics to Drive Occupancy

00:24:40 - Market Share / Portfolio Size

00:25:12 - Policy Analysis: Cleaning Fees Across Managers

Get FREE Access to our Community and Weekly Trainings:

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In this episode, we break down the systems, hiring moves, and mindset shifts that free you from the day-to-day grind—so you can grow faster.

• Why you always need that next big goal

• The real reason we become entrepreneurs: time control

• How to qualify and hire your first key player

• Setting up turnover checklists that run without you

• The role that keeps properties guest-ready every day

• Why you must have someone who can step in for you

• The investment that buys back your time

• How to stop micromanaging and reacting to fires

00:04:03 - Why you always need that next big goal

00:04:01 - The real reason we become entrepreneurs: time control

00:10:35 - How to qualify and hire your first key player

00:09:25 - Setting up turnover checklists that run without you

00:01:06 - The role that keeps properties guest-ready every day

00:13:57 - Why you must have someone who can step in for you

00:00:01 - The investment that buys back your time

00:19:51 - How to stop micromanaging and reacting to fires

Get FREE Access to our Community and Weekly Trainings:

http://group.strsecrets.com/

From attracting 30 members to the mastermind to tactical takeaways from a 2000+ person event, we break it all down.

• Why raw content works better than polished

• The one onboarding question that reveals true goals

• STR WealthCon recap: biggest takeaways

• How to get ROI from live events

• The vibe shift in the STR community

-

Want to get crystal clear on your goals and scale your STR business?

Click the link below to book a discovery call and see if our Mastermind is the right fit for you.

Link: https://go.strsecrets.com/podcast?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T023&utm_content=Clear

-

00:03:01 - Raw Content That Converts

00:05:55 - Massive Takeaways From WealthCon

00:08:42 - Unlock Event ROI Secrets

00:11:32- Mindset Shift Every Host Needs

00:14:25 - Behind the Scenes of a Power Launch

00:16:54- High-Impact Networking Tips

00:19:32- Underrated Gold From Live Events

00:22:21 - Mastering the Referral Flywheel

00:25:06- Growth Hacks for Ambitious Hosts

Get FREE Access to our Community and Weekly Trainings:

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But they’re not designed for how people actually *live.*

In this episode, guest architect Zeke Freeman shares the hidden design flaws baked into most houses — and how his process reshapes spaces around *real human behavior.*

Whether you’re remodeling a home, designing an Airbnb, or dreaming about your next property, this episode will flip how you think about space, function, and flow.

What you’ll learn:

- Why most homes don’t reflect how people actually use them

- How to design with *invisible behavior patterns* in mind

- The “door test” for practical flow in short-term rentals

- Why your home may be sending the wrong emotional signals

- Zeke’s process for uncovering how a space wants to work — before you build

00:01:15 - Designing Identity: From Architecture to Personal Branding

00:04:32 - Why Architects Make Great Entrepreneurs

00:07:58 - Thinking in Systems: A Superpower for Founders

00:10:40 - Applying Space Planning to Business Structure

00:14:06 - Designing Offers Like Floor Plans

00:17:21 - Why Constraints Fuel Creativity

00:21:44 - How Messaging Is Like Structural Engineering

00:26:02 - From Drafting Buildings to Drafting Funnels

00:30:55 - The Hidden Layer of Brand Architecture

00:35:19 - Why Most Founders Skip the Blueprint Phase

00:40:46 - Using Architectural Thinking to Scale Operations

00:45:10 - Form Follows Function in Business Too

Guest Bio:

Zeke Freeman is a visionary architect, builder, and passionate advocate for the transformative power of design. With over two decades dedicated to shaping the realms of hospitality and Colorado's modern design, Zeke has emerged as a leader in boutique hotels, hospitality development, and strategic business management. As the CEO of TheRootTeam, which includes an international team of Architects, an estate brokerage, and a Hospitality Development Company, Zeke Freeman has not only left an indelible mark in Colorado Architecture but has also steered the company towards its 12th year of success, bringing many beautiful projects and many more impacted lives together across the Front Range. Zeke is also the host of the RADicalhospitality show, which explores the intersection of Architecture, Development, and Hospitality.

Guest Link:

https://linktr.ee/zfreeman1

Get FREE Access to our Community and Weekly Trainings:

http://group.strsecrets.com/

In this episode, Adam breaks down the 5 core sales frameworks he teaches to high-performance closers in STR and beyond.

From reframing rejection to diagnosing like a doctor, this is the mindset, structure, and clarity that separates amateurs from closers.

What You’ll Learn:

• The “doctor frame” for every sales call
• Why connection > charisma
• The mindset shift every new closer must make
• Why your pitch must pass the “grunt test”
• How sales becomes your ultimate life skill

Guest Bio:

With over $100 million in sales to his name, Adam Stein brings a rare mix of high-performance sales strategy and human-centered communication to the mic. Having taken more than 4,000 sales calls and reviewed over 10,000, he's coached and led sales teams from startup scrappers to 9-figure juggernauts. An avid golfer and father of two awesome boys, Adam blends psychology, mindset, and real-world sales mastery to help entrepreneurs sell with confidence, clarity, alignment, and compassion.

00:04:31 - Learning from a high-level sales mentor changed everything

00:08:54 - Overcoming mindset blocks was the first real sales battle

00:13:04 - Sales is philosophy — not just tactics

00:17:26 - Old-school sales techniques don’t work in STR anymore

00:21:58 - Great salespeople are obsessed with discovery

00:26:12 - Your pitch must pass the “grunt test”

00:30:35 - If you don’t believe in what you’re offering, they’ll feel it

00:34:48 - Diagnosing like a doctor earns trust and conversions

00:39:10 - Sales is service when done with integrity and empathy

Guest Link:

https://www.instagram.com/the.salesscientist/

Get FREE Access to our Community and Weekly Trainings:

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This episode breaks down exactly why $150K–$200K is now the minimum to win, and how to outpace the competition by investing in what actually matters.

You’ll learn:

• How Mike’s team turned a $715K property into a 26%+ cash-on-cash winner

• Why outdated listings are getting crushed in today’s market

• The new furnishing rule of thumb (hint: it’s not $6K per room anymore)

• Why “I’ll add amenities later” is the biggest red flag from investors

• Real-world examples of design ROI and creative deal structuring

• How to dominate Year 2 with direct bookings, not just Airbnb

If you’re serious about STR, this episode will shift how you think about budget, value, and building long-term cash flow.

-

Want bookings before you're even done renovating?

Just click the link below to get the Free Training.

https://go.strsecrets.com/podcast?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T022&utm_content=PreLaunch

-

00:03:30 – Budget Furniture and Low Investment No Longer Work in B or C Markets

00:05:00 – Reinvesting in Amenities Can Revive Underperforming Properties

00:07:15 – Pre-Launching With Mood Boards Can Generate Bookings Before Renovation Ends

00:09:03 – Investing More in Amenities Can Double or Triple Cash-on-Cash Returns

00:13:02 – You Need Direct Bookings—Don’t Rely Only on Airbnb and VRBO

00:15:01 – You’re Competing on ADR Only If You’ve Maxed Out the Amenity Strategy

00:23:29 – Borrow Amenities From Other Markets to Win in Your Own

00:25:16 – Don’t Wait to Upgrade—Do It Upfront or You’ll Lose Money

Get FREE Access to our Community and Weekly Trainings:

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In this episode, Patrick breaks down his roll-up strategy for short-term rental management businesses, focusing on Joshua Tree.

You’ll learn:

• How to value STR property management companies

• The hidden formula top performers are using (4.9+ reviews + max RevPAR)

• How he’s creating additional revenue from Netflix, OF shoots, and more

• The underrated power of real hospitality, hyper-local service, and partner alignment

This isn’t just about scaling, it’s about building a legacy business in a saturated market.

00:00:11 - Become the Local Expert, Not a Nationwide Manager

00:08:45 - Three Business Lessons from Open Water Swimming

00:09:03 - Use a Roll-Up Strategy to Scale Management Companies

00:10:00 - Study High-Performing PMs for 4.9+ Ratings at Scale

00:11:20 - How to Value and Buy STR Management Companies

00:13:32 - Use Off-Market Outreach to Acquire Small Managers

00:17:00 - Full-Service PM is the Only Way to Compete in Joshua Tree

00:21:22 - Add Production Shoots to Maximize Weekday Revenue

00:25:45 - How to Get Featured by Netflix and PR Agencies

00:35:00 - Partnerships are Marriages—Choose and Lead with Trust

Guest Bio:

Patryk Swietek is a 28-year-old entrepreneur with a background in building tech companies since the age of 14. Ever since getting into real estate at 24 years old, he's been a thought leader in the STR industry, teaching the co-hosting model with his own Amazon best seller book and online podcast. He scaled from 5 of his own properties to managing over 100 signed properties in Joshua Tree in under 1 year. He has bought 3 STR co-hosting companies to become the #1 co-host in one of the most competitive vacation rental markets in the country. His company and homes have been featured on Netflix, Wall Street Journal, NY Times, Dwell, etc.

Guest Link:

https://www.instagram.com/patryk_swietek

Get FREE Access to our Community and Weekly Trainings:

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In this episode, we break down exactly how the short-term rental tax loophole works, how you can use it to eliminate 5–6 figures of taxable income, and what rules you must follow to stay IRS-compliant.

Whether you own 1 property or manage dozens, this is one of the most powerful tools in your financial playbook.

You’ll Learn:

• Why this loophole can save you $40K+ per property

• The 2 conditions to qualify for non-passive treatment

• How cost segregation studies supercharge your deductions

• Why co-hosts & PMs can charge consulting fees using this

• What to avoid if you don’t want the IRS to audit you

Want to directly talk about taxes and how you can make use of the tax loophole for STRs? Just click the link below:

https://go.strsecrets.com/podcast?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T021&utm_content=Taxes

00:05:08 – Powerful Tax Strategy to Slash Your Income

00:06:01 – How One Property Saved Me $92,000 in Taxes

00:09:02 – Must-Know Criteria to Unlock STR Tax Benefits

00:09:11 – Track This or Risk Losing Your Tax Deductions

00:10:16 – Use It Wrong, Lose It All

00:12:03 – Avoid This Common Mistake with Friends and Family

00:13:04 – How to Legally Save $40,000 with Depreciation

00:16:06 – Transform OK Deals Into Great Ones

00:17:17 – A Brilliant Offer Property Managers Should Use

Get FREE Access to our Community and Weekly Trainings:

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In this episode:

• Jeff’s journey from VRBO and Expedia to Furnished Finder

• Why monthly rentals are the most underserved niche in real estate

• How to price your MTR listings for max profit

• The 3 types of hosts who thrive on Furnished Finder

• Tech upgrades, new guest demographics, and the future of midterms

• Why most Airbnb hosts still don’t understand real returns

Whether you’re a casual host or a pro operator, this episode will help you rethink your strategy, lower your fees, and build a more resilient rental business.

Guest Bio:

Jeff Hurst is the President and CEO of Furnished Finder, a role he assumed in November 2023 at the invitation of the company’s founders. Prior to that, Hurst was the Chief Operating Officer of Expedia Brands and Co-Lead of Expedia Group Marketing. Before that, he was the President of Vrbo and Chief Strategy Officer of HomeAway, where he oversaw the company’s successful sale to Expedia, Inc. Before venturing into the vacation rental industry, Hurst worked as a consultant at McKinsey & Company, collaborating with consumer brands on corporate strategy, mergers and acquisitions, and pricing strategies. Hurst received his MBA from the Stanford Graduate School of Business and BA from the University of Texas at Austin.

00:05:00 - Game-Changing Insights: Luxury Brands in Vacation Rentals

00:10:00 - Unstoppable Leaders: CEOs Who Shaped My Philosophy

00:15:00 - Winning Balance: How I Prioritize Family, CEO Role, & Life

00:20:00 - Bold Moves: Why I Chose Furnish Finder Over Other CEO Jobs

00:25:00 - Secret Advantage: Choosing the Right City & Team First

00:30:00 - Proven Blueprint: Advice to My Son on Career & Leadership

00:35:00 - Power Tip: Best Way to Reconnect with Furnish Finder

00:40:00 - Ultimate Secret: #1 Tip for Short Term Rental Success

00:45:00 - Smart Hack: How Hosts Save Money by Reverse-Engineering Airbnb

Guest Link:

https://www.linkedin.com/in/jeff-hurst-atx

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

In this episode, we break down exactly what changed and what to do about it.

Here’s what you’ll learn:

• Why Airbnb is auto-switching hosts to a “Firm” policy, without clear consent

• What happened to the original Strict policy (spoiler: it’s weaker now)

• The difference between “Strict,” “Firm,” and the new “Limited” cancellation options

• Real refund scenarios, who gets paid when guests cancel

• Why Mike is switching to “Limited” on all new listings

• How to check if your policy was changed (and how to fix it)

Don’t let Airbnb rewrite your house rules without you knowing.

Want to get the latest Airbnb Policy One-Pager?

Just click the link below and DM the word "Policy".

Link: https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T020&utm_content=Policy

00:00 - Airbnb Cancellation Policy Changes & How To Adapt

01:24 - Choosing the Right Cancellation Policy: Strict vs Firm vs Limited

02:49 - How To Use Rank Breeze To Track Your Airbnb Rankings

04:14 - Opting Out of Airbnb’s Forced Policy Changes

05:39 - How New Listings Are Affected By Airbnb’s Updated Rules

07:04 - Strategies for Competing in Saturated STR Markets

08:29 - Building Repeat Clients & Getting Direct Bookings

09:54 - Protecting Against Chargebacks With Rental Agreements

11:19 - Know Your Market’s Booking Window & Adjust Policies

12:44 - Using Tools Like AirDNA & Rank Breeze To Optimize Revenue

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

In this episode, you’ll learn:

• Why most first-time hosts shouldn’t expect a profit (and what to aim for instead)

• The $65K reno gamble that paid off, plus how to pitch owners to invest

• 5 non-negotiables every STR investor needs to check before buying

• How to match properties to real investor goals (not hype)

• What to say when a listing has bad photos, ugly furniture, and zero bookings

• How to turn stale listings into discounted wins using seller credits

• The mindset shift that helped turn their lowest income year into their highest ever

Whether you’re starting from scratch or trying to turn things around, this episode is packed with honest advice and real numbers to help you grow the right way.

Don’t go it alone, learn from people who’ve already done it.

00:01:14 - Revenue Boost: Previous Owner’s $30K Shows Untapped Potential

00:05:05 - Hustle Story: From Mowing Lawns to Building Wealth

00:09:37 - Mindset Shift: Realizing It Was Never Just a Job

00:13:00 - Profit Jump: Small Changes, Big Revenue Growth to $70K

00:16:54 - Unique Selling Point: Win Without a Pool

00:19:31 - Client Filter: Say ‘No’ More Often to Grow Stronger

00:20:42 - Investor Clarity: Aligning with Each Investor’s True Goal

00:22:45 - Negotiation Win: Securing $130K in Seller Credits

00:26:29 - Host Reality: Why Airbnb Won’t Help When It Matters

Guest Bio:

Joe Rohne bought my first two short-term rentals in 2022, one with his wife and one with a business partner. Within three months, he shifted into cohosting and picked up 2 cabins in Branson. Joe went to the STR Wealth Conference and met a bunch of people. From there, he started his own cohost mastermind to have weekly calls and help each other grow. He grew to 12 mostly luxury cohost properties. Joe sold his first two STRs in 2024 and upgraded to a larger luxury property, and is looking to buy another this year. All this turned into him having a co-host podcast and helping others get into this space. He has been a realtor for 5+ years in St. Louis, and got his license in Florida to sell in Panama City Beach, which is where the majority of his STR business is. In August 2024, Joe got linked with Tyler and the Savvy team, and he is now building a team that services the entire panhandle. He currently has ten co-hosts and one owned property.

Guest Link:

facebook.com/joe.rohne

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

Just 18 months later?

He runs 37 listings, left his W-2, and built a profitable, freedom-filled business, all without using his own capital.

In this episode, we break down exactly how he did it:

• The red flags in his arbitrage model that forced a pivot
• How he turned losses into leverage with a co-hosting pitch
• A case study that took one property from $90K → $211K
• The “Underserved Investor Method” for finding hidden gems
• Why volume doesn’t matter, precision does
• And the system he used to scale without capital or burnout

If you’re stuck, tired, or scaling blindly, this might be the episode that saves your business.

00:00 - Burned Out at 11 Units, Freedom at 37: The Mark Story

00:01 - Rising Rents and Saturation: Why Arbitrage Fails

00:04 - Audit and Pivot: How a Simple Portfolio Audit Changes Everything

00:05 - Switch to Co-Hosting: Scale with No Capital

00:06 - The Design ROI Pitch: Turn $10K Into $33K Fast

00:09 - Underserved Investor Method: Find Hidden Gems Others Miss

00:12 - $30K Redesign → $211K Revenue: Real Numbers, Real Proof

00:13 - Fire Bad Managers: Care Wins Big

00:14 - Small but Mighty: Profit Without Massive Volume

00:15 - Cohosting Margins: 50%+ With Full Teams

00:16 - Don’t Blame Pricing: Fix Your Offer and Model Instead

00:17 - Raise the Bar: Better Hosts, Better Homes, Better Industry

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

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
• Her playbook for turning burnout into purpose-driven success

Tools & strategies for STR → MTR pivots, burnout recovery, and branding with integrity.

00:35 - Never Build Your Whole Business on Someone Else’s Platform

06:03 - Building a Strong Real Estate Brand Identity

07:01 - How to Be Known in Your Network to Grow Your Business

13:00 - Choosing the Right Community to Plant Roots for Business & Life

16:17 - Growing from STR to MTR: Changing Ownership Structures

17:33 - Airbnb Kicked Me Off: The Risk of Platform Dependence

19:20 - Switching from Short-Term to Mid-Term Rentals: Why & How

25:00 - Why Midterm Rentals Mean Better Clients & Less Work

26:12 - Using AI and Custom GPTs for Marketing and Operations

30:51 - Becoming a Relocation Specialist: Multiple Income Streams

33:02 - Smart Branding: Pick a Consistent Name & Handle

34:28 - Niche Marketing: Speaking Directly to Your Avatar

39:46 - Sharing Authentic Life Stories to Build Audience Trust

43:53 - First Aid Kit for Burnt Out Hosts: Breathwork, Meditation, Nervous System Health

48:35 - Success Secret: A Never-Quitting Mindset

Guest Bio:

Amanda Williams, widely known as The Traveling Realtor, is a seasoned real estate entrepreneur, eXp Realty agent, and visionary behind Carolina Furnished Rentals (CFR). Founded in 2019, Carolina Furnished Rentals skyrocketed in 2020 as demand for longer stays surged during the pandemic. This pivotal success became a lifeline in 2021 when Amanda was unexpectedly removed from Airbnb through no fault of her own—a common challenge for many hosts relying solely on third-party platforms.

Rather than seeing it as a setback, Amanda turned this challenge into an opportunity to take full control of her business, doubling down on the mid-term rental (MTR) model. She transformed Carolina Furnished Rentals into a thriving enterprise, proving the power of owning your brand and building a business independent of volatile platforms.

Today, Amanda uses her expertise to help Airbnb hosts with 5+ properties transition to the stability and profitability of MTRs. Through her 30-Day MTR Sprint Program, she provides hands-on coaching, automation strategies, and proven systems to help property owners scale smarter, reduce headaches, and create a business they truly own.

Amanda’s mission is simple: empower others to build wealth, freedom, and a brand they’re proud of while navigating the ever-changing rental landscape. From coaching clients to speaking at events, Amanda inspires hosts to take control of their future and achieve financial independence on their own terms.

Guest Link:

https://www.instagram.com/amandathetravelingrealtor/

Get FREE Access to our Community and Weekly Trainings:

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...it’s your offer.

In this episode, we walk through how to dominate even when bookings slow down, using frameworks that helped our clients grow from 0 to 100+ properties (without lowering their standards).

Inside, you’ll learn:

• The 2 sales you must make to land AND grow every client
• How to niche down with an offer big managers can’t touch
• Why “boutique” isn’t enough (and what to say instead)
• ChatGPT + Hormozi = your unfair advantage
• The COHOST sales framework that turns owners into clients fast

If you’re tired of feeling stuck in the cohosting middle zone…This is the episode that unlocks your next 10 doors.

Want to generate your Perfect Offer? Just click the link below to get the ChatGPT Prompt:

https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T018&utm_content=Prompt

00:00 – Stand Out or Stay Stuck: Why Differentiation Is Non-Negotiable

00:12 – The COHOST Framework: A Proven Sales Funnel for STR Growth

00:45 – Survive the Booking Slump: Why Traditional Markets Are Struggling

02:44 – Don’t Panic Price: How to Maximize Occupancy Without Slashing Rates

04:48 – The #1 Mistake: Thinking Being Small Automatically Wins Trust

05:15 – Riches in Niches: Hyper-Focus Your Property Strategy

07:00 – The Plus-One Strategy: Tiny Add-Ons That Win Big Contracts

10:33 – STR Takeover Transformation: Craft an Offer They Can’t Refuse

14:59 – Risk-Reversal Guarantees: The Ultimate Owner Conversion Tactic

21:00 – Make STRs Great Again: Why Boutique Operators Are the Future

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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 breaks 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 never sleeps

If you’re still running 80% of your business manually…this episode will change that.

03:00 - Audit Your Inner Voice to Align with the Life You Want

07:00 - Step Into Your Vision by Speaking It Out Loud

10:00 - Optimize Sales Calls Using Custom GPT Feedback Loops

12:30 - Write High-Converting Listings and Titles with AI

14:00 - Do Market Research, Regulations, and Pricing with GPT

15:30 - Automate and Personalize Guest Messaging at Scale

17:00 - Generate Social Media and Website Content with ChatGPT

19:00 - Streamline Hiring, SOPs, and Onboarding with AI

22:00 - Analyze Property Performance and Build Offers with GPT

Get FREE Access to our Community and Weekly Trainings:

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In this episode, we break down exactly what’s coming, why this event will never happen again, and how to make the most of it.

What you’ll learn:

• Why this is the last WealthCon hosted by Mike & Bill

• The new format designed for all STR business levels

• Speaker highlights: Cody Sanchez, Pace Morby & more

• The 9 deep-dive masterclasses (creative finance, hotels, scaling)

• Real deals, partners, and freedom stories born from past WealthCons

• VIP & Diamond perks: elite networking, pre-events, premium access

• Mike’s “Generational Wealth Blueprint” sneak peek

Whether you’re coming or just curious, this is the behind-the-scenes breakdown you need.

Learn more about the 2025 STR Wealth Conference

https://na.eventscloud.com/ereg/index.php?eventid=829193&discountcode=MEMBERSONLYCLUB

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02:58 – Why This Is the Final STR WealthCon

04:50 – Scaling from 15 to 2000+ Attendees in 3 Years

06:45 – Why This Will Be the Most Impactful STR Event Yet

07:17 – Keynote Power: Cody Sanchez, Pace Morby & Business Mastery

12:00 – A Brand-New Generational Wealth Roadmap (Never Shared Before)

15:26 – Networking Blocks: How Deals Worth Millions Begin

17:20 – Raising Industry Standards: How Better Hosts Beat Regulation

20:03 – How to Build a Business That Runs Without You

Buck scaled two.

In this episode, we break down how he went from managing one unseen unit in Nashville to running a 70-property short-term rental operation and a digital marketing agency at the same time.

No fluff, just systems, AI, and strategic growth.

What you’ll learn:

• How he jumped from 5 to 20 units with one key client
• The team structure and cashflow strategy that saved them in winter
• Using AI + Hormozi to craft irresistible offers
• The “$10 / $100 / $1K / $10K” time block system
• Why smart maintenance = higher reviews and retention

If you’re building a real business, this one’s a blueprint.

04:48 – How One STR Outperformed 4X and Sparked a Business

10:55 – Cleaning & Tech Enabled Remote STR Scaling

13:27 – Investor Stepped In During Cash Flow Crisis

15:05 – Zig When Competitors Zag: Break Industry Norms

17:00 – 5-Star Guarantee: No Commission Without Reviews

20:01 – Flat-Fee Maintenance Boosts Property Standards

24:00 – Focus on $1K and $10K Tasks to Scale Faster

Guest Bio:

Buck Cumbo is the owner of www.seamountainvacations.com. He is managing nearly 50 million dollars in assets amongst 60+ properties in the Myrtle Beach area. Buck have also recently been brought on as Brand Director at www.theonehundredcollection.com.

Guest Link:

http://www.instagram.com/captain_buck_

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

It’s called “Services,” and it lets guests book things like chefs, trainers, and masseuses without your approval, while you carry all the liability.

In this episode, I break down:

• Why this new feature is dangerous for pro hosts
• How to opt out in 3 steps
• How to beat Airbnb at its own game by building your own Services page
• Why relying on Airbnb in 2025 is a bigger risk than ever

If you’re serious about building a business (not just listing properties), this is mandatory viewing.

03:04 - The Hidden Risk for Hosts: Guests Can Book Services Without You Knowing

04:45 - Host Liability Risks From Airbnb Services

05:55 - How Bad Service Experiences Can Hurt Host Reviews

07:00 - Why Airbnb Rolled Out Services Without Consulting Hosts

08:15 - The Simple 3-Step Process to Opt Out of Airbnb Services

10:28 - Why Hosts Must Act Now: Collective Opt-Out Pressure Matters

13:00 - How to Add a “Services” Tab to Your Direct Booking Website

16:00 - Partnering With Local Providers Can Lead to Repeat Guest Referrals

19:00 - Will Opting Out of Services Affect Airbnb Search Rankings?

22:00 - Airbnb Is Targeting Hobby Hosts—What It Means for Pros

23:30 - Why You Must Diversify Beyond Airbnb and Build a Real Business

26:05 - STR Secrets Fulfillment Strategy for Different Host Levels

Guest Link:

instagram.com/boostlyuk/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

Diana and Josh, two married architects, were forced to reimagine their future after losing both their fathers in 2021.

What began as a journey to escape the W-2 grind became Terra Palm Springs, the city’s first true wellness boutique hotel.

They reveal how they:

• Pivoted from flips and BRRRRs into commercial real estate

• Used their design and construction edge to underwrite with vision

• Created immersive guest experiences that transcend hospitality

• Built three synergistic businesses to scale with intention

• Took bold action while honoring their deepest personal “why”

This story will move you, inspire you, and give you a real blueprint for building a brand, and a life that matters.

What You’ll Learn:

• How to spot your unfair advantage (and actually use it)

• The key to underwriting without inflating projections

• What makes a boutique hotel truly stand out

• How to transition from short-term rentals to hotel ownership

• Why generosity is the secret weapon in hospitality

00:00 - Action drives clarity

00:35 - Process-proven growth

01:36 - Power couple feature

02:20 - Life-changing loss

05:55 - Strategic shift to scale

07:26 - Expert system builders

09:50 - Value-add obsession

10:56 - Underwrite with confidence

14:30 - Unapologetic branding

16:42 - First-of-its-kind wellness hotel

21:00 - Team-powered execution

25:40 - The real estate awakening

28:00 - Finding purpose through pain

31:30 - Create your unfair advantage

36:00 - Future-built freedom

43:00 - Hospitality secret: give generously

Guest Bio:

Diana and Josh Dobken have 15+ years of experience in the architecture and construction industries. They strategically invest in value-add opportunities where they can use their design expertise to maximize their return on investment. Additionally, Diana and Josh co-host 35+ MTRs and STRs across multiple states for other real estate investors, bringing their hospitality standards and design sensibility to each property we manage.

Beyond property investment, Diana and Josh also manage comprehensive operations teams for hotels, with them overseeing director of operations roles and guest experience management. This hands-on operational experience gives them invaluable insights into how design decisions impact day-to-day functionality and guest satisfaction.

Their most current project involves the Architectural and Interior design of Terra Palm Springs, the first wellness Boutique Hotel in Palm Springs featured in Vogue, Forbes, Hotels Above Par, and selected as part of Travel and Leisure It List of 2025’ 100 Best New Hotels in the World.

Guest Link:

http://www.instagram.com/d.i.fi

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

From custom comps to Airbnb integration, this episode breaks down the new features, how to use them, and what they reveal about the 2025 STR landscape.

What you’ll learn:

• How to use the new Rentalizer confidence score and custom comps
• Why saved projections and expense tracking are game changers
• The truth about 2025 booking trends (and who’s winning)
• What AirDNA’s forecast says about rates, RevPAR, and smart investing

If you’re serious about short-term rentals, you can’t afford to miss this.

Want to get our Latest Deal Analyzer?

Just click the link to our Instagram below and send 'Rentalizer'

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02:35 – Why the Update Matters: Major Interface and Logic Changes

05:10 – Data Model Shift: From Historical to Projected Revenue

08:00 – The 3 Core Metrics You MUST Understand in the New Version

11:00 – Updated Filters: Comp Selection and Market Targeting

13:30 – Accuracy Considerations: What AirDNA Gets Wrong (and Right)

16:45 – Real-Time Demo: Using the New Tool to Analyze a Property

20:20 – How to Reverse Engineer a Successful STR Deal with AirDNA

24:00 – Hidden Pitfalls: Common Mistakes People Make Post-Update

28:10 – Strategic Recommendations for Using the New Rentalizer

Get FREE Access to our Community and Weekly Trainings:

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What happened next?

A wild ride through the world of short-term rentals, driven by family, strategy, and a long-term vision few operators ever reach.

In this episode, Fouad breaks down:

• How a personal medical emergency forced him to buy his first Airbnb
• Why most operators price listings wrong—and how he uses math instead
• The real difference between luxury and comfort STRs (and why he runs both)
• His custom tech stack using Go High Level
• And the real reason he’s scaling to $12M/year before exiting

This one’s for the operators who want to scale smart, stay profitable, and build something sellable.

What you’ll learn:

• How to scale with dual verticals (luxury + comfort)
• Why you must reverse-engineer around your exit
• How banking lessons apply directly to STRs
• Why pricing = math, not emotion
• How Fouad thinks about purpose and legacy

Ready to build a business that banks would beg to fund?

Fouad shows you how.

03:30 – Breaking the Golden Handcuffs: Why He Left Corporate

07:00 – First STR Deal: Starting Small With Big Vision

10:00 – Smart Risk: Learning to Bet on Yourself

13:00 – From 1 to 10+ Units: Scaling With Confidence

17:00 – Wealth Mindset: Thinking Like an Owner, Not an Operator

20:00 – Cash Flow vs Time: Redefining Success Metrics

24:00 – Building a Business, Not a Job: Systems and Team Growth

27:00 – Lessons From the Field: What He’d Do Differently

30:00 – Purpose-Driven Investing: Time, Family, and Freedom

Guest Bio:

Fouad Bazzi is a professional in the short-term rental (STR) industry. His activities include owning, managing, and building new build-to-rent properties, as well as consulting and educating others in the STR space. He also owns a pool servicing company that specializes in serving STR properties.

Guest Link:

https://www.instagram.com/fouad_airbnb

Get FREE Access to our Community and Weekly Trainings:

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In this live breakdown, we cover:

• The truth about Airbnb’s new “Services” feature and why it matters

• What this means for photographers, chefs, massage therapists, and YOU

• How Airbnb plans to monetize add-ons (and why you might not see a cut)

• Major liability concerns Airbnb isn’t talking about

• How this could affect your guest experience—and your reviews

• Why this is really a pivot toward becoming the Instagram of Travel

Plus: actionable strategies to get ahead of this change, build local service partnerships, and protect your property.

TLDR? This update means more work for hosts, unless Airbnb starts paying us to help them grow. Watch this now so you’re not caught off guard.

Want to get the summary of Airbnb's Latest Update?

Just click the link to our Instagram below and send 'Update'

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00:00 – Bold Shift: Airbnb’s 2025 Release Redefines the Platform

01:30 – Major Update 1: Cleaning Services Now Offered to Guests

04:00 – Major Update 2: Handy Services and Maintenance on Demand

06:30 – Control at Risk: Services Can Be Scheduled Without Host Approval

08:45 – Host Autonomy Undermined: Who Has Access to Your Property?

10:30 – Guest Experience Prioritized: Host Voice Being Muted

12:00 – Airbnb’s Strategic Shift: From Booking Site to Service Ecosystem

13:30 – Host Action Plan: Communicate, Audit, and Prepare

Get FREE Access to our Community and Weekly Trainings:

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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 founder.

Whether you’re a startup founder, STR operator, or tech junkie—this is a must-listen for anyone who wants to win big without burning out.

Ready to scale? Tap into Marcus’s billion-dollar playbook now.

00:00 – Go Bigger: Why Playing Small Carries the Same Risk but Less Reward

00:39 – Craft Over Hype: The Power of Repetition and Mastery

02:04 – Be There: Why Leading Remotely Doesn’t Win Markets

03:45 – Market Leadership: How Hostaway Beat Older, Bigger Players

05:58 – Hiring Giants: From 50,000 Applicants to the Top 0.1%

08:59 – Cost of Ambition: Health, Relationships, and the Real Price of Building

12:29 – Go for Billionaire Moves: Why Medium Goals Aren’t Worth the Sacrifice

15:31 – Choosing Good Money: Partnering with Investors Who Let You Lead

17:23 – No Kitchen Rules: Keeping Creative Control While Scaling Up

20:27 – Invisible AI: How Hostaway Uses Tech to Deliver Unseen Excellence

23:00 – Review Intelligence: Turning Guest Feedback into Business Strategy

25:30 – Tool Advantage: Hostaway’s Marketplace as a Growth Engine

27:17 – Global Expansion: Owning New Markets One Continent at a Time

29:33 – Regulation Shakeout: Why Strong Rules Are Good for Professionals

32:50 – Reputation Reset: Cleaning Up the Industry with Standards That Matter

Guest Bio:

Marcus Räder is co-founder and CEO of Hostaway, the leading all-in-one vacation rental management software. Originally from Finland, Marcus has lived in many countries around the world including Sweden, Poland, and The Netherlands before settling in Canada. It was this passion for travel, real estate and his dedication to learning about the vacation rental ecosystem that enabled the creation of Hostaway.

The company quickly grew thanks to the deep technological expertise of its founders, with over a decade of tech start-up success between them. Hostaway gives property managers all the tools needed to compete with hotels and other vacation rentals, including sales channel management, dynamic pricing and hospitality services. It now boasts preferred partnerships with Airbnb, Vrbo and Booking.com, in addition to a marketplace of over 100 integrated software partners.

Guest Link:

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

Get FREE Access to our Community and Weekly Trainings:

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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

• The exact moment a founder must pivot from operator to people leader

• How to use the 5 Dysfunctions of a Team framework to build culture that scales

• Why emotional safety is the hidden growth lever most CEOs ignore

• And how to actually implement event takeaways before you lose momentum

This isn’t another tech tips episode.

It’s a tactical and vulnerable deep dive into what it takes to scale, lead, and stay grounded in 2025.

00:00 – Building Confidence: Lessons from Struggle, Sales, and Self-Belief

04:00 – Rewiring Identity: From Overwhelm to Intention

08:00 – Leveraging Chaos: Why Adversity Becomes Your Superpower

12:00 – The Four Levels of Competence: From Unconscious to Mastery

16:00 – Winning in Business: Simplifying Systems, Offers, and Time

20:00 – $20K Days in 5 Hours: Prioritizing High-Leverage Work

24:00 – Clarity Is Power: Why Lack of Decision-Making Kills Momentum

28:00 – Excuse Audit: The Hidden Stories That Keep You Small

32:00 – Emotional Regulation: How to Respond Instead of React

36:00 – Final Challenge: Step Into Power and Choose a New Story

Get FREE Access to our Community and Weekly Trainings:

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…but because they don’t have a system.

In this training, Mike and Chris break down the 3 proven models for hiring virtual assistants.

Agency, recruiter, and self-hire.

Plus the crucial 4R framework you need before bringing anyone on.

Whether you’ve got 5 properties or 100+, this is the training that saves you from wasted money, broken systems, and constant turnover.

What you’ll learn:

• The 3 types of VA hiring models (and when to use each)

• The biggest reason your VA won’t work out (it’s not what you think)

• How to build a talent pipeline that scales with your portfolio

• When to hire for skills vs culture fit

• Bonus: Where to find agency + recruiting referrals we actually trust

_

Want to get the FREE VA Contract and 4R Doc?

Just click the link to our Instagram below and send 'Contract'

https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T013&utm_content=Contract

00:00 – Hiring Roadmap: Breaking Down the VA Models

02:00 – Agency Model Explained: Training Wheels for Scaling Leaders

05:00 – Recruiting Model: Upfront Investment, Long-Term Efficiency

08:30 – Self-Hiring Secrets: Full Control, High Risk, High Reward

11:00 – Referral Power: Leveraging A-Players to Source Talent

13:30 – Cultural Pitfalls: The Hidden Risk in Team Referrals

16:00 – Specialty Roles: Revenue Management vs. Marketing VAs

19:00 – Creating Execution Frameworks for Social & Brand Marketing

22:00 – Revenue Management Mastery: Metrics, Mindset, and Misconceptions

25:00 – Bonus Resource: Contract Templates & Legal Protections for VA Hiring

Get FREE Access to our Community and Weekly Trainings:

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They’re missing decision.

In this episode, Mike and Emanuele break down the 5 mindset philosophies that transformed their lives...

...from escaping burnout and W2 jobs to building multi-million-dollar businesses and raising families with time freedom.

If you feel like you keep “trying” but never break through, this episode will call you out...

...and pull you forward.

What you’ll learn:

• The most powerful reframe for taking back control of your life
• Why saying “I’ll try” guarantees failure
• How to train your decision-making muscle daily
• The “day one” philosophy that separates top performers from the rest
• A no-fluff breakdown of time vs. money thinking (and how to escape the trap)

Ready to finally commit?

This is your line in the sand.

00:00 - Uncovering Transformational Beliefs that Redefined Success

04:00 - Embracing Radical Ownership: Life Happens *For* You

09:35 - Unlocking Growth Through the Day One Philosophy

14:30 - The 4 Powerful Stages of Skill Development

18:20 - Tactical Time vs Money: Rewriting Productivity Rules

22:00 - Designing a $20K Month in 5 Hours: The Value-Driven Hustle

26:30 - Eliminating Excuses: Breakthrough Decisions that Shape Destiny

31:10 - The Critical Power of Fast Decision-Making

33:00 - Rethinking Reality: Story, Meaning & Inner Peace

35:00 - Final Challenge: Cut the Dirty Yes, Choose Powerfully

Get FREE Access to our Community and Weekly Trainings:

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In this episode, Mike breaks down the 7 most common mistakes that silently ruin guest experiences and the reviews that follow.

These aren’t theories.

They’re field-tested lessons from 1,200+ reviews, across 28 properties, and over 5 years of hosting.

You’ll learn:

• Why nickel-and-diming your guests kills conversion
• The #1 amenity guests expect (but almost no one provides)
• How to stop losing stars from poor messaging and over-automation
• Why Photoshop and misleading listings backfire (fast)
• The deep clean schedule every top host follows
• How to protect margins while leveling up experience
• The review-killer most hosts don’t realize they’re doing

If you’re stuck at 4.8 and can’t crack 4.95+, this is your fix.

05:00 – Algorithm Boost: How Amenities and Photography Drive Ranking

06:00 – Lightning Response: The Profit Power of Immediate Communication

08:00 – Misleading Listings: The Hidden Cost of Photoshop and Fluffed Locations

11:00 – Guest-Friendly Pricing: Stop Nickel-and-Diming for Add-Ons

13:00 – Annual Investment Rule: Keeping Properties Fresh and 5-Star Worthy

15:00 – The Upgrade Clause: Property Improvement Plans That Scale Value

17:00 – The Cleanliness Factor: Deep Cleaning Every Quarter Pays Dividends

19:00 – Messaging Mistakes: Why Over-Communication Kills Guest Experience

21:00 – Final Recap: 7 Things Hosts Do That Secretly Cost Them Reviews

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

AirDNA’s Chief Economist Jamie Lane joins the show to break down what’s actually happening behind the scenes in the short-term rental market...

...and why most hosts are missing the shift.

Inside this episode:

• The real story behind occupancy, rates, and guest demand in 2024
• Why “big box” managers are losing properties fast
• The key numbers top investors are watching (and how to use them)
• How AirDNA’s new tools are reshaping STR deal analysis
• The warning signs for hosts scaling past 50 units and what breaks first
• Why small, well-managed portfolios are quietly outperforming everyone

You’ll also hear how Jamie’s team is using AI and custom comps to bring never-before-seen clarity to STR investing...

...and what you can do to stay ahead.

Listen now to future-proof your portfolio before the data leaves you behind.

03:30 – Supply Shock: Why New STR Listings Are Surging Nationwide

07:00 – Booking Behavior: How Travelers Are Changing Their Habits

10:00 – Revenue Realities: The Decline in ADR and Occupancy Rates

13:30 – Market Saturation: Top Cities Facing Over-Supply Pressures

17:00 – Strategic Advantage: How to Win in Competitive Markets

21:00 – Data-Backed Decisions: Using AirDNA to Stay Ahead

24:00 – The Investor Shift: From Arbitrage to Ownership Models

27:00 – Resilience & Risk: Preparing for Softening Demand Cycles

30:00 – Long-Term Outlook: What Smart Operators Are Doing Next

Guest Bio:

Jamie Lane is Vice President of Research for AirDNA, a short-term rental data & analytics company. He is responsible for data analysis, thought leadership, and leveraging advanced analytical techniques to provide new insights into short-term rental supply, demand, and pricing trends. He has been published in academic and professional journals and regularly speaks at lodging industry forums.

Prior to AirDNA, Jamie spent 10 years as an economist at CBRE, leading research, forecasting and data intelligence teams to support client analysis. Mr. Lane is an active member of the National Association of Business Economists and the Atlanta Economics Club. Jamie holds a B.S. in Economics from the University of Georgia and an M.S. in Business Economics from Georgia State University.

Guest Link:

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

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

Ashley Freeman wasn’t supposed to be here.

Divorced, struggling to make ends meet as a tennis pro.

She took a chance on Airbnb with her farmhouse.

Now she manages over 105 units, leads a team of 25……

and lives a life most people only dream about.

In this powerful episode, Ashley reveals:

• How a side hustle became a 7-figure business
• The mindset shifts that changed everything
• Why systems + a strong team scaled her from 4 to 100+ properties
• How she created a 5-star guest experience that owners can’t stop raving about
• The identity shift required to step into true leadership

Success doesn’t happen overnight.

It happens when you refuse to quit.

Listen now and see how Ashley built an empire…

…one step, one belief, and one property at a time.

03:30 – From Rock Bottom to Rising Entrepreneur: Ashley’s Journey

07:00 – Faith, Grit, and Overcoming Self-Doubt in Business

10:00 – Rebuilding Self-Image: How Belief Rewires Success

13:30 – Tactical Scaling: Systems, Team Building, and Leadership Lessons

17:00 – Secrets to Sustainable Growth: Mindset, Service, and Strategy

20:30 – Life by Design: Building Freedom Through STR Success

24:00 – Living the Dream: Redneck Ranch, Soccer Travels, and Family First

Guest Bio:

Ashley Freeman is a 7-figure short-term rental expert who transformed her life through the power of short-term rentals. Starting with just one property, she scaled her business to 105 properties in under three years, growing from less than $50,000 in her first year to $2 million annually by year three, with the support and mentorship of STR Secrets and Conway Consulting. Passionate about serving others, Ashley is dedicated to helping people find the same freedom and life-changing opportunities that the short-term rental business gave her.

Guest Link:

https://www.instagram.com/velvet_ditch_villas

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

If you collect emails, drop a guidebook link, or offer guests early check-in via Venmo…

You might be in violation of Airbnb’s new policy.

In this episode, Mike Reilly breaks down exactly what Airbnb’s new off-platform & fee transparency rules mean for STR hosts.

And how to stay compliant without losing control of your business.

You’ll learn:

• The exact actions Airbnb will now penalize (even by AI detection)
• Why asking for an email could get you flagged
• How to safely use guidebooks, QR codes, and text marketing
• The only way to charge guests for add-ons (without breaking policy)
• The smart way to collect damage waivers and manage taxes without risk

If 80% of your bookings come from Airbnb, you can’t afford to get this wrong.

02:30 – Dangerous Moves: Why Secret Messaging Will Get You Flagged

05:00 – Booking Extensions & Repeat Guests: What’s Now Off-Limits

07:30 – Is Direct Booking Worth It? Margins vs Platform Protection

10:00 – Hostfully Links, Guidebooks & Legal Loopholes Explained

13:00 – Mandatory Disclosures: HOA Rules, Emails & County Compliance

15:00 – Fee Transparency: Avoiding Suspensions With Clean Listings

18:00 – Payment Violations: Why Airbnb Bans Zelle, Venmo & Side Deals

21:00 – Damage Waivers Over Deposits: How to Protect and Profit

24:00 – Airbnb AI Enforcement: Messaging Triggers and Flagging Risks

27:00 – Contact Info Restrictions: What You Can and Can’t Ask Guests

30:00 – SMS Tactics: Getting Verbal Consent and Staying Compliant

33:00 – Future-Proofing: Will Airbnb Eliminate Direct Contact?

36:00 – Review Removal Struggles: Why AI Appeals Are Failing Hosts

39:00 – Case Study: Retaliatory Reviews & the Fight for Fairness

42:00 – Platform Fatigue: Why Community Knowledge is Your Best Weapon

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

Ron Curtis didn’t quit his job.

He just built a business so efficient that he didn’t have to.

In this episode, Ron breaks down how he:

• Turned a $3,700 house hack into a 50-property portfolio
• Cleared over $10K in credit card debt and now manages $300K in available credit
• Uses his 9–5 income to fuel real estate moves without burnout
• Built systems, VAs, and SOPs to scale without stress
• Teaches financial literacy by living it, not just posting about it

You’ll also learn:

• Why relationships > money in cohosting
• The mindset shift that tripled his capacity
• And how he helped one client buy a $1M building, just from Airbnb cash flow

This episode is proof you don’t need to quit to win.

04:30 – Market Momentum: Flips, Deal Flow, and Fear-Based Opportunity

09:00 – Financial Literacy First: Foundational Principles for Entrepreneurs

13:30 – Zero to Fifty Listings: Scaling with Systems and Strategic Partnerships

18:00 – Designing Teams for Freedom: SOPs, VAs, and the Org Chart Blueprint

22:30 – The Mindset Shift: Working On the Business, Not In It

27:00 – Simplify to Scale: Letting Go of the Noise and Focusing on ROI

31:30 – Buying Back Time: Vertical Integration and Efficiency Hacks

36:00 – Real Client Wins: How STR Cashflow Changed Lives and Bought Freedom

41:00 – House Hacking & Books That Sparked a Million-Dollar Portfolio

Guest Bio:

Ron Curtis is a native Washingtonian and the founder of a short-term and mid-term rental management business based in the Washington, DC area. Ron's journey into short-term rentals started with house hacking—he leveraged first-time homebuyer programs to purchase his first home, a turnkey $423,000 property, for just $3,700 out of pocket. He converted his basement into a studio efficiency and listed it on Airbnb. As Ron traveled, he realized his basement was consistently booked and covering his mortgage. That’s when he fell in love with the concept of Paycations—earning passive income while exploring the world. He built an automated, scalable business model that allows him to manage rentals from anywhere with just WiFi and a reliable cleaning team. Over the last 3.5 years, he has organically grown from managing one property to 50—all while working a full-time 9–5 government job in DC. Ron loves to share his insights on scaling a short-term rental business, automation strategies, and how others can achieve financial freedom through short-term rentals.

Guest Link:

www.instagram.com/wavy_stay

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

Everyone’s complaining about deals not working.

But here’s the truth...

...it’s not the market; it’s your property.

In this episode, we break down:

• Why most STRs fail to hit pro forma in today’s market
• How one $700K Pinehurst property generated $45K in bookings in 5 weeks
• What amenities are actually driving bookings in top markets
• How to design listings that feel different (and rank higher)
• Simple ROI math for cold plunges, saunas, and garage conversions

You’ll also learn how Airbnb is shifting toward experiential stays.

And how to make sure your listing stands out in a sea of sameness.

Don’t wait for the perfect deal. Create it...with the right design and data.

04:00 – Targeting Travel Avatars: Niche Down to Maximize Bookings

06:00 – Real Case Study: How a $700K Property Secured a Celebrity Booking

08:00 – Pre-Launch Tactics That Drove $12K in Bookings Without Photos

10:00 – Benchmarking & Amenity Differentiation in Saturated Markets

12:00 – ROI on Amenities: Saunas, Cold Plunges & Game Rooms

14:00 – Pinehurst Playbook: Amenity Investments That Drive ADR Growth

16:00 – Tailoring Amenities to Market: Golfers, Families & Regional Travel Types

18:00 – Algorithm Hacks & Listing Design That Trigger Emotion and Visibility

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

Emanuele Pani went from mopping floors and fixing leaks…to owning nearly every unit in his building.

But success wasn’t what he expected.

In this episode, you’ll hear:

• How he bought 39 out of 40 units using seller financing & hustle
• What happened when COVID hit, no grace period, no backup plan
• The creative deals that made it all possible (and profitable)
• Why burnout and identity loss followed after the win
• How he rebuilt his purpose with long-term hospitality and legacy in mind

This isn’t a how-to. It’s a how-he-did-it.

From broke to burned out and back to intentional growth.

04:30 – From Cleaning Units to Closing Deals: The Hustle Years Begin

09:00 – Bold First Move: Buying 12 Apartments with No Credit

13:30 – Managing Chaos: Mortgages, Maintenance, and Mentality

18:00 – Refinancing & Reinvesting: How One Refi Fueled the Next Level

22:30 – Rising Too Fast: Distractions, Syndications, and Burnout

27:00 – The Redemption Plan: 18-Unit Acquisition Through Sheer Will

31:30 – Pandemic Pivot: Surviving COVID with Mid-Term Mastery

36:00 – The Final Two: Closing the Hardest Sales with Strategic Leverage

41:00 – Full Circle Wealth: STR Structure, Community, and Long-Term Vision

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

In this episode, Tyler Coon and Mike Reilly dive into what’s really happening across the short-term rental market in 2024...

...and where the smart money is moving.

You’ll learn:

• Why low-end properties are disappearing (and what replaces them)
• How investors are multiplying profits through equity exits
• What upgrades are actually producing 50%+ cash-on-cash returns
• The biggest mistake STR hosts make with property design and amenities
• Why boutique cohosts and local managers are beating big-box operators

The STR industry is consolidating, and only the best will survive.

05:30 – Luxury Dominance: The Future of Short-Term Rentals

08:30 – STR Consolidation: Why Only the Top 10% Will Thrive

11:00 – Strategic Renovation: High ROI From Over-Investing in Design

13:30 – Sleeping 30: Big Groups, Bigger Opportunity

16:00 – Building a Moat: Unique Amenities That Lock In Demand

18:30 – Recession-Proof Strategy: Why Luxury Still Wins in Downturns

20:30 – Equity Moves: Sell or Reinvest for Maximum Return

23:30 – Portfolio Power: Scaling with High-Performing Assets

Get FREE Access to our Community and Weekly Trainings:

group.strsecrets.com

It’s not your strategy.

It’s not your effort.

It’s your identity.

In this episode, mindset coach Adam reveals how shifting his subconscious beliefs helped him triple his income in just 8 months……without changing his work ethic.

You’ll learn:

• Why you attract what you feel, not what you say you want

• How to rewire limiting beliefs using emotional repetition

• Why most goals fail without identity alignment

• The daily 30-minute practice that transforms your vibration

• Why real estate, business, or coaching success starts in the mind

Hard work isn’t enough.

Change your inner world

……and watch your outer world follow.

04:00 – Breaking Point: Transformational Moments that Spark Change

08:00 – Identity Shift: Reprogramming Your Self-Image for Success

12:00 – Unshakable Ownership: Facing Hard Truths to Reclaim Power

16:00 – Debunking Limiting Beliefs: Where They Come From & How to Break Free

20:00 – Emotionalization Mastery: Embodying Beliefs That Attract Results

24:00 – Regulate to Rewire: The Role of Nervous System in Manifestation

28:00 – Vibrational Alignment: How Feelings Shape Reality

32:00 – Real-World Manifestation: From Vision to Deal in 3 Days

36:00 – Integration & Flow: Anchoring the Inner Work into Real-Life Wins

Guest Bio:

Adam Avenus is a mindset and manifestation coach who has spent the last 8 years learning about neuroscience, quantum physics, spirituality and the psychology behind the production of extraordinary results. He found this work first through meeting a coach while he was selling Real Estate, and she helped him triple his income in 8 months. After experiencing what he thought was ‘success’ selling real estate, he started building a company in the software space, came and worked at STR Secrets, and built a small management company, all before going all in on his coaching business. When Adam first found his work, he made $4,000/month and was depressed. Now, he has made over $100,000 last month and have never felt more free or peace in his life. 

Webinar Link:

https://go.avenusconsulting.com/quantumleapmasterclass

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com