Explore every episode of the podcast Short Term Rental Secrets Podcast

He was working 80 hours every two weeks in a hospital ICU.

Open heart surgery patients. Life or death. No room for error.

And in the gaps between shifts, sometimes still in his scrubs, he was quietly building a short term rental business that would set him free.

In this episode, E sits down with Jeremy Rosen for one of the most honest W2-escape stories this show has ever told.

Jeremy joined STR Secrets with 4 properties and a full-time nursing job he loved but knew he had to leave. He went from 4 to 8 to 12 to 20 properties, all while clocking 12-hour shifts at the VA. Then he merged his company into Five Star Vacation Rentals, now running 67 properties across Central Texas, and finally walked away from nursing for good.

In this episode:

→ The exact mindset shift that took Jeremy from sick patients to happy guests, and the nurse's instinct that makes him a better host than most operators will ever be

→ How he used his days off, while everyone else scrolled, to prospect, sell, and grow

→ The "who not how" decision that broke him out of doing everything himself, and the one hire that changed his entire business

→ Why he refused to build in secret, and how speaking his goals out loud actually made them happen

→ The honest truth about quitting your W2 that almost nobody talks about, including the strange struggle of suddenly owning all of your own time

→ Why "everything is figure out able" is the only belief you need to finally make the leap

If you have a good job you're scared to leave, this is the episode you need to hear.

Free 6-step course to start your day right: level.strsecrets.com/pc-book

Join the community: STR Secrets Facebook Group

His wife said something to him that he'll never forget.

"I would let every business burn to the ground if it meant that when it's nighttime and on weekends, we could spend it as a family."

Dave Menapace didn't argue. Didn't defend himself.

He sat with it. And then he changed everything.

In this episode, E sits down with STR Secrets coach and Five Star Co-Host founder

Dave Menapace — on his birthday — for a raw, unfiltered look at four years of

building, burning down, and rebuilding a short-term rental management company

the right way.

Dave left corporate healthcare in April 2022 with two STRs and a vision.

Four years later, he's managing 58 properties. He signed number 58 this morning.

But the path there? It looked nothing like what he planned.

In this episode:

→ The "seven streams vs. seven jobs" mistake that keeps most operators broke

and burned out — and how Dave finally broke the cycle

→ How he started Five Star Co-Host over from scratch after realizing

he'd built it wrong the first time

→ The $100K IRA withdrawal that gave him the team he needed to grow

→ Why he went from 30 properties to 58 in just 5 months — and the three

obsessions that made it possible

→ The $80,000 trust account crisis that hit in September 2025 — and why

his response to it doubled the business

→ What it actually takes to build a management company worth $100M

(and why Dave believes it's just a choice)

This is not a highlight reel.

It's the version of the story most people are too scared to tell.

Want to connect with Dave? Find him on Instagram: @dave_menapace

Join the community: STR Secrets Facebook Group

Free 6-step course: level.strsecrets.com/pc-book

Timestamps:

00:00 - "Seven streams of income is not seven jobs"

08:07 - Leaving corporate, WealthCon, and the birth of Five Star Co-Host

15:48 - The Miami pool moment Kim told E: "my husband is doing a million things"

32:21 - The most important thing Kim ever said to Dave

35:45 - The three obsessions that unlocked 30 to 58 properties in 5 months

48:17 - The $80,000 crisis and what focus does under pressure

"🔥 LAST CHANCE — STR AI SUMMIT, June 23-24 | Freedom Factory, Beverly, MA

Only 10 seats left

. This is where direct bookings, AI agents, and the next decade of STR get built — live, with the operators leading the charge.

👉 strsecrets.com/aisummit

Most STR operators don't have an information problem.

They have an identity problem.

In this solo episode, mindset coach and STR Secrets co-host Emanuele Pani

breaks down the framework he's been using inside the weekly STR Secrets mindset

calls — and explains exactly why so many operators stay stuck despite doing

all the right things.

If your results haven't caught up to your effort, this episode is for you.

What you'll learn:

→ Why goals are working against you — and why standards change everything

→ The thermostat analogy: why your belief system resets your results back

to where they've always been

→ The LOVE framework for breaking old identity patterns (Liberate, Optimize,

Velocity, Elevate)

→ Why external validation from clients is a ceiling on your business

→ The one question that shows whether your internal story matches

your external goals

→ E's 5 daily affirmations and exactly how to use them morning and night

📘 Free 6-step STR course: level.strsecrets.com/pc-book

💬 Join us: STR Secrets Facebook Group

Timestamps:

00:00 - Why E goes to Italy every summer (and what it actually cost to get there)

09:00 - Stop setting goals. Start setting standards

12:00 - The LOVE framework: how to free yourself from old stories

16:00 - The thermostat analogy: why doing the work is not enough

20:00 - Three questions to ask yourself right now

23:00 - The 5 affirmations that reset your identity every single day"

🔥 LAST CHANCE — STR AI SUMMIT, June 23-24 | Freedom Factory, Beverly, MA

Only 20 seats left. Use code "PODCAST" for a flat $1000 discount:

👉 strsecrets.com/aisummit

The coupon expires Monday

This is where direct bookings, AI agents, and the next decade of STR get built — live, with the operators leading the charge.

Yorkshire, UK — Mark Simpson spent $50,000 on human appointment setters last year. They did almost nothing.

Then he built one AI agent named Icarus. In 7 days, it closed a $5,000 deal. Cost? Less than $20.

Two months later, Mark has 18 AI agents running inside Boostly. They've generated $54,000 in revenue. And he says he's never hiring a human setter again.

Mark Simpson is the founder of Boostly — the company helping STR operators escape over-reliance on Airbnb and own their direct bookings. He grew up on a farm in North Yorkshire, where his family ran a BNB. Over the last decade, he's refined the most complete direct bookings playbook in the vacation rental industry. Now on his 7th appearance on the show, he's back with the rawest, most honest take on AI agents we've had to date.

This is his blueprint for direct bookings, AI agents, and what's about to happen to operators who don't adapt.

What you'll learn:

→ Why Mark predicts Airbnb's commission is going from 15.5% to 20% — and what the data shows

→ The 65% direct booking goal — and why going 100% direct is just as dangerous as 100% Airbnb

→ The 3 things every direct booking website needs that 90% of operators still get wrong

→ The exact story of Icarus: how Mark built his first AI agent in 2 days and made his money back in 7

→ How Boostly went from a team of 20 to a team of 150 without hiring a single human

→ Why 0.05% of people pay for AI Pro — and how $18 a month puts you in the top 99.5% globally

→ The "18 minutes a day" rule that quietly turns operators into AI power users

→ How Mark trained his entire 22-person team on AI without overwhelming a single person

→ The honest answer to "are you teaching your team to replace themselves?"

→ Why "the cream rises to the top" — and which roles are about to disappear

🎙️ Guest: Mark Simpson | Founder, Boostly

🔗 Website: https://www.boostly.co.uk

🔗 Boostly Connect: https://boostlyconnect.com

🔗 LinkedIn: Mark Simpson

🔗 Instagram: https://www.instagram.com/boostlyuk

🔗 Facebook: https://www.facebook.com/mrmarksimpson

🔗 Book recommendation link: http://bit.ly/2WEOm1v

─────────────────────────────

⏱️ TIMECODES

─────────────────────────────

00:00 - The $50K wasted on human setters and the AI agent that changed everything

01:32 - Mark Simpson returns for his record-breaking 7th episode

02:15 - Life update: 4 kids, World Cup tickets, and the UK trip this summer

03:29 - "Don't build your home on someone else's land" — Mark's signature line

04:00 - Airbnb's fee hike from 3% to 15.5% — and why he saw it coming in 2022

04:30 - The next prediction: why Airbnb is going to 20% commission

06:38 - Top 3 things every operator needs to start direct bookings TODAY

07:02 - Why WordPress still wins in 2026 (and why your PMS landing page isn't a real website)

08:54 - When to flip from "this is a hobby" to "this is a business" (around property 6-7)

09:30 - Why exit-ready businesses always have strong direct booking revenue

11:51 - What does "good" look like? The 65% direct booking benchmark

13:49 - The two-part myth: high-converting website AND content/SEO effort

14:27 - Why hospitality operators are spoiled — and why that's a problem

16:40 - The fundamentals of business that STR operators keep ignoring

17:26 - The "do you know anyone" referral mindset most operators are too scared to use

19:55 - The mirror moment: who do you actually blame for missing your goals?

20:36 - AI agents — Mark's full breakdown starts here

20:57 - Why The Matrix in 1999 still defines how Mark thinks about AI

22:00 - The OpenClaude story: how one weekend GitHub project broke the industry open

24:50 - The breaking point: firing the $50K setter and going all in

25:30 - Meet Icarus — Mark's first AI agent (and the Greek myth behind the name)

26:00 - Real result: $5,000 booking closed in 7 days for under $20 in AI costs

26:30 - 18 agents, $54,000 in revenue, 2 months later

27:19 - Reality check for the shiny object chasers

29:00 - "I'm an idiot" — Mark on why anyone can do this

30:00 - All 22 Boostly employees now have their own AI agent

31:30 - The Google Chrome extension a non-technical team member built in one week

33:00 - The $18 Pro plan stat: why 99.5% of the world isn't paying yet (and what that means for you)

34:00 - The 18 minutes a day rule that compounds into mastery

35:00 - How Mark rolled AI out to his team without overwhelming anyone

36:30 - Comet by Perplexity: the agentic browser changing how teams work

38:04 - "Aren't you teaching them to replace themselves?" The hard question

38:55 - Mark's brutally honest answer (it's not what you think)

41:27 - Why AI Agent Manager is the #1 role being hired for right now

41:51 - The danger of going 100% AI (same risk as going 100% direct)

43:21 - Life on the human side: paddle, books, and saying goodbye to soccer

44:43 - 6 hours back in his day — what Mark plans to do with it

46:55 - The two killers of every operator: lack of attention and poverty of imagination

47:41 - Boostly Connect — the free tool that pulls your PMS data anywhere

49:04 - Mark's #1 secret to AI agent success: just start

─────────────────────────────

🎁 FREE RESOURCES

─────────────────────────────

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

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

Boostly Direct Booking Playbook (Mark's book): http://bit.ly/2WEOm1v

Boostly Connect (free up to 10 listings): https://boostlyconnect.com

─────────────────────────────

🔥 STR AI SUMMIT — June 23-24 | Freedom Factory, Beverly, MA

The exact AI systems Mark talks about in this episode? They get built with you LIVE at the summit.

Don't just listen to the playbook. Leave with it installed.

Only 100 seats.

👉 strsecrets.com/aisummit

─────────────────────────────

#ShortTermRental #DirectBookings #AIforSTR #Boostly #STRSecrets #VacationRental #PropertyManagement #AirbnbInvesting #AIAgents #STRScaling

Ryan will be showing how to make this and a custom revenue management tool live at the Ai Summit. Grab your spot at the AI Summit: strsecrets.com/aisummit at just $497. Use the coupon : "PODCAST"

Every homeowner conversation starts the same way.

They want to know what their property can earn.

And if you can't answer that question fast, professionally, and with data behind it —

someone else will.

In this week's training, Mike sits down with STR Secrets coach Ryan Lefebvre to

demo the AI-powered comp analysis tool that's helping property managers turn more

conversations into signed contracts.

Ryan went from 1-2 comp requests a week to 10 a week — from realtors and investors

who now send him every new listing because he delivers branded, data-backed reports

in minutes, not hours.

In this episode:

→ The exact tool Ryan built using Claude that generates a full comp report in

2 to 10 minutes (vs. 20-30 minutes manually)

→ How to use conservative, base, and optimistic revenue projections to handle

any homeowner conversation on the spot

→ Why realtors are becoming one of the fastest referral pipelines for new

management contracts — and how to tap in

→ The AI rabbit hole warning: why building your own tools can quietly kill

your business growth

→ Mike's financial freedom math: exactly how much you need invested to hit

$100K a month in cash flow

→ Why arbitrage is a dead end — and what the data on the biggest arbitrage

companies actually shows

This is not theory. Ryan runs live comps during the session on real properties

submitted by the audience — you'll see exactly how the tool works in real time.

and we'll send it straight to you.

Ready to install this and a full AI system for your business live?

Timestamps:

00:00 - Intro & Ryan Lefebvre's background

01:42 - From financial crime analyst to AI builder for STR

04:22 - How the comp tool works and what it produces

06:33 - Live demo: running an Airbnb listing in real time

09:26 - Interactive sliders and revenue scenario conversations

11:17 - How to handle bad comps and sparse markets

13:36 - Live demo: running a property address

17:34 - How the tool handles off-market or renovated properties

22:38 - Using comp reports to show homeowners the gap between unmanaged and managed

26:41 - AI Summit: what's being covered and who's speaking

29:04 - Ticket pricing and how to register

32:02 - Alex case study: 2 properties to 35 in one year

35:29 - The AI rabbit hole warning

38:00 - Using AI at any portfolio size

41:06 - Mike's financial freedom math ($8M at 15% = $1.2M/year)

44:46 - Why arbitrage is a dead model

49:27 - Should you replace your channel manager with AI? (No. Here's why)

52:45 - Q&A: summit details, recordings, revenue manager AI tool

🔥 Get $500 off at STR AI SUMMIT — June 23-24 | Freedom Factory, Beverly, MA

Use code "MEMORIAL500" while checking out at strsecrets.com/aisummit

You're doing the work. You're managing the properties. You're showing up every day.

So why does it feel like you're spinning your wheels?

In this solo show, Chris Petzy and Emanuele Pani get raw about the real reason STR

operators stall out — and it has nothing to do with the market, your pricing strategy,

or your occupancy rate.

In this episode:

→ The 3 silent causes of business stagnation (and which one is quietly killing your

growth right now)

→ Why split focus will never equal scale — and the one decision Chris made that

changed everything

→ The identity gap: how to stop making decisions from who you've been and start

making them from who you're becoming

→ E's 5 daily affirmations that rewire how you start every single day

→ Why hiring for today's need is the biggest mistake scaling operators make

If the last six months didn't go the way you planned, this episode is your reset.

Ready to build the business that funds the life?

Apply to work with us: strsecrets.com/apply

Get Carrie the AI Carousel Sniper Agent: https://level.strsecrets.com/drrachel

🔥 STR AI SUMMIT — June 23-24 | Freedom Factory, Beverly, MA

Dr. Rachel is flying in to spend 2 full hours building this exact system with you live.

You won't just learn it. You'll leave with it installed. Only 70 seats left.

👉 strsecrets.com/aisummit

Most STR operators know they need to post more. They just don't have the time, the team, or the system to do it.

Dr. Rachel Gainsbrugh does. And in Portfolio Clinic Episode 8, she pulls back the curtain on the exact AI content engine she built to generate weeks of social content without living on her phone.

Dr. Rachel is a former full-time physician turned full-time real estate investor, entrepreneur, AI strategist, and founder of Short Term Gems. She built her entire content system out of necessity — and now it runs largely without her.

In this episode, Mike Sjogren sits down with Dr. Rachel to walk through the full system live: from raw meeting notes to scheduled carousels, with AI agents doing most of the heavy lifting.

What you'll learn:

→ The 7-11-4 rule: why buyers need 7 hours of content across 11 touchpoints on 4 platforms before they trust you enough to write you a check

→ Meet Vega — the AI agent that processes all your meeting notes every night and sorts them into content, SOPs, and coaching opportunities before you wake up

→ Meet Carrie — the carousel sniper that takes one Airbnb link and delivers 10 ready-to-post carousels including captions and CTAs

→ Meet Contesta — the content queen that formats everything for each platform and sends it to scheduling automatically

→ How a property manager with 80 doors sent 60 personalized owner emails in 2 hours (he used to spend his whole weekend on it)

→ How to train your AI like an employee using SOPs — and why that one step changes everything

→ The AI data privacy protocol that keeps your sensitive files in a sandbox and out of reach

→ Why posting once or twice a week means you are already losing to operators using this system

🎙️ Guest: Dr. Rachel Gainsbrugh | Founder, Short Term Gems

🔗 Get Carrie the Carousel Sniper Agent: https://level.strsecrets.com/drrachel

─────────────────────────────

⏱️ TIMECODES

00:00 - Cold open: Carrie the carousel sniper demo — one Airbnb link, ten carousels

00:57 - Mike and Dr. Rachel intro — why she's the go-to AI person in the space

01:34 - Dr. Rachel's background: from full-time doctor to AI-powered STR investor

02:13 - The 7-11-4 rule: the Modern Trust Formula every operator needs to understand

03:04 - Two content angles for STR operators: repeat guests and new client acquisition

03:39 - Why Dr. Rachel built this system (she hates being on camera)

05:24 - The note taker habit that turns every meeting into a content asset

05:48 - The Plaud Note Pin: the wearable AI recorder Mike and Rachel swear by

07:09 - Meet Vega: the AI night agent that sorts all your meetings while you sleep

07:53 - How Vega triages every meeting into four buckets before you wake up

08:15 - Real demo: Vega identifies a coaching frame used 14 times across calls and flags it

09:23 - 425 meetings reviewed by AI that no human ever had time to touch

09:56 - How Vega processes data directly from Fireflies, Otter, and Plaud using schema

13:22 - Step two: turning the content database into actual social posts with Contesta

13:58 - Real proof: 80-door property manager sends 60 personalized owner emails in 2 hours

14:22 - How Contesta routes content to Phoebe (Facebook) and schedules it automatically

15:15 - How Mike applies this to property walkthroughs and hotel renovation updates

16:14 - Why guest reviews are an untapped content goldmine most operators ignore

17:20 - The one thing Dr. Rachel warns against: asking AI to write posts with no context

18:05 - How to sell through your real stories: the three-part owner acquisition framework

19:15 - Mike's local events agent: scraping tourism data to feed newsletters and social

20:18 - Why showing your journey (not the polish) is what builds trust and drives bookings

21:46 - Meet Carrie: the carousel sniper — live demo walkthrough

23:11 - Carrie in action: pulling property photos from Airbnb, building 8-10 slide carousels

24:50 - Guest reviews as carousel slides: 122 reviews turned into content automatically

25:29 - Carrie delivers: full carousel batch plus caption, CTA, and downloads folder

26:00 - Is all of this through Claude? Yes — Claude Co-Work and Claude Code

27:04 - How long it took to build Carrie (two months) and how fast it runs now (one command)

28:44 - Train AI like an employee: the SOP-first method for consistent results

29:49 - Real world result: executive assistant elevated from admin to EA after AI frees her up

31:47 - Dr. Rachel is speaking at the AI Summit — two full hours of live building with you

33:43 - How to train Claude with SOPs, PDFs, and audit loops

35:26 - AI quality is only as good as your SOP — garbage in, garbage out

36:31 - Who owns your property photos? What every operator needs in their photographer contract

37:19 - The Night Janitor: the AI agent that organized 16,000 photos and files in minutes

39:15 - How to talk to Claude about your messy photo library and get a real solution

41:05 - Claude Code vs. Claude Co-Work: when to use which for scheduling and automation

41:35 - Should you have separate social accounts for owner acquisition vs. guest direct bookings?

43:49 - Training AI vs. training humans: why right now is the best time to be an operator

47:02 - AI Summit preview: June 23-24, Freedom Factory, Beverly MA — build it live with Rachel

48:19 - The volume reality: someone using this system is posting 3x a day while you post twice a week

─────────────────────────────

🎁 FREE RESOURCES

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

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

#ShortTermRental #AIforSTR #STRSecrets #VacationRental #PropertyManagement #ContentStrategy #AirbnbInvesting #AIAgents #DirectBookings #STRScaling

🔥 STR AI Summit — June 23-24 | Freedom Factory, Beverly, MA

Only 100 seats. Built for operators who are serious about what comes next.

👉 strsecrets.com/aisummit

If you're managing 5, 10, or 50+ properties and wondering whether AI is a tool or a threat — Marcus Räder has the answer. And it's not what most people are saying.

Marcus is the co-founder and CEO of Hostaway — the first vacation rental software company to reach unicorn status and the recipient of the largest funding round in vacation rental history: $365 million led by General Atlantic.

He's been in this industry for over a decade. He's seen every wave. And right now, he's more excited — and more concerned for unprepared operators — than ever before.

In this episode, E and Chris sits down with Marcus for one of the most candid, far-reaching conversations in the show's history. From AI and private equity to running 100 marathons in 100 cities — this one goes deep.

What you'll learn:

→ Why private equity is circling STR operators right now and what it means for your business valuation

→ The #1 thing AI can't do for your properties (and where most operators are dangerously overconfident)

→ Why "more data = more visibility" is the new SEO — and how to make your listings AI-search-proof

→ The direct booking strategy that still works in 2026 (the basics haven't changed as much as you think)

→ How to build a team that thinks 3 years ahead when they're wired to think about today

→ The honest truth about building a big business vs. just being great at your job

→ What losing 70 pounds and running 17 marathons taught Marcus about scaling anything

🎙️ Guest: Marcus Räder | Co-Founder & CEO, Hostaway

🔗 Connect: https://www.linkedin.com/in/marketingmarcus/

🌐 Website: hostaway.com

─────────────────────────────

⏱️ TIMECODES

─────────────────────────────

00:00 - The hard truth: adapt to AI or lose guests to someone who did

02:01 - E & Chris reconnect — scaling conference takeaways + the Sardinia deal update

05:39 - Introducing Marcus Räder: building Hostaway into a $1B business

08:50 - Living the hybrid US-Europe life with family (7 months abroad)

11:48 - Hostaway's origin story: from channel manager to full PMS to $365M raise

14:03 - What it actually feels like to run a unicorn — the founder's relationship with time

16:20 - How to build a team that thinks years ahead when employees focus on today

17:34 - Why Marcus's best hires came from web hosting, not STR

19:37 - AI in STR: excited or worried? Marcus's honest take from the CEO seat

21:47 - The viral meme that perfectly exposes the DIY AI trap

22:45 - What STR operators really do during peak season (it's not what you think)

23:06 - Where AI fails: raccoons, hurricanes, guest injuries, and edge cases

24:15 - How Hostaway built its AI control layer for guest communications

27:00 - Build in-house vs. stay third party: Marcus's framework for scaled operators

28:33 - The hidden danger of AI models that silently update and change answers

29:41 - The Uber lesson every STR operator needs to hear right now

31:25 - Will AI become a race to the bottom? Where monetization is heading

32:07 - The pool pump disruption: how AI reshapes maintenance costs and who profits

34:00 - "Findability" — go ask AI to find YOUR property right now and see what happens

35:15 - Why private equity is turning STR businesses into 10x assets with AI

36:18 - What the next decade of Hostaway looks like

38:33 - Direct bookings in 2026: the dead-simple strategy most operators still skip

39:26 - Why your listing description is failing AI search (and the wall of text fix)

41:42 - Data is the new currency: whoever gives AI the most wins the booking

42:13 - Build big or go work for someone — Marcus's hard truth about entrepreneurship

43:13 - 100 marathons in 100 cities: the health journey and what flat feet taught him

47:07 - The calorie analogy that explains how small disciplines compound at scale

49:36 - Marcus's #1 secret to STR success: boring, consistent, and most people skip it

─────────────────────────────

🎁 FREE RESOURCES

─────────────────────────────

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

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

─────────────────────────────

#ShortTermRental #AirbnbInvesting #STRSecrets #VacationRental #PropertyManagement #STRScaling #AIforSTR #Hostaway #DirectBookings #RealEstateInvesting

Join use at the STR AI Summit — June 23-24 at the Freedom Factory in Beverly, MA. 100 seats only strsecrets.com/aisummit

Mike Sjogren spent over $5,000 in API credits in two months learning AI the hard way. And he wants to make sure you don't have to.

In this Portfolio Clinic training, Mike breaks down the top 10 AI mistakes that cost him real money — from not understanding context windows to memory file bloat to giving an agent 15 tasks at once and wondering why nothing got done. He then walks through exactly how STR operators should be using AI right now across three buckets: getting more properties, getting more bookings, and getting more time back.

He also shows how he rebuilt his Florida direct booking website in under a day for under $200 using Manus, how his AI agent scrapes top boutique hotel social media content overnight and delivers a morning brief, and why the goal is never to build your own software — it's to use AI as a bolt-on to everything you already have.

DM Mike on Instagram @mike.sjogren and comment PROMPT to get the free PDF of all the prompts he used to build his direct booking website.

STR AI Summit — June 23-24 at the Freedom Factory in Beverly, MA. 100 seats only.

strsecrets.com/aisummit

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 Mike Is Doing This Training (And How Much It Cost Him)

2:15 - Mistake #1: Not Understanding Context Windows ($6 Per Message)

5:30 - Mistake #2: Memory File Bloat — Why AI Gets Dumber Over Time

7:45 - Mistake #3: Using Your Most Expensive Model for Everything

10:00 - Mistake #4: Broken Cron Jobs — How to Schedule Tasks That Actually Run

13:00 - Mistake #5: Treating AI Like an Employee Who Can Handle 15 Things at Once

16:30 - Mistake #6: Not QC-ing the Output

18:00 - Mistake #7: Trying to Build Your Own PMS or Pricing Tool

20:30 - The 3 STR Buckets: More Properties, More Bookings, More Time

23:00 - How to Use AI to Automate Your Entire Prospecting Pipeline

27:00 - How to Use AI to Get More Bookings Right Now

30:00 - How to Rebuild Your Direct Booking Website With AI for Under $200

36:00 - How Mike's Overnight Agent Scrapes Top Hotel Content Every Night

39:00 - The 10 Rules for Using AI Without Burning Your Budget

42:00 - How to Motivate Your Team to Use AI Without Fear

46:00 - Where to Start If You're Brand New to AI

48:00 - STR AI Summit: June 23-24 at the Freedom Factory

🎟️ Join us at the STR AI Summit — June 23-24 at the Freedom Factory in Beverly, MA.

Only 100 seats. Early bird: $1,497.

strsecrets.com/aisummit

Tying your identity to your door count is the fastest way to burn out—or worse. In 2008, Rod Khleif lost $50 million. He calls it an expensive "seminar."

In this episode, E sits down with Rod to discuss how he rebuilt his massive real estate portfolio by fundamentally changing his peer group and his mindset.

Today, Rod's students own over 260,000 units, and he has fed more than 160,000 children through his Tiny Hands Foundation. He breaks down the massive demographic shift he calls the "Silver Tsunami"—why the demand for senior housing is about to explode, and how his team is acquiring assisted living facilities for $40,000 a door.

He also shares a massive wake-up call regarding Artificial Intelligence, explaining exactly how his own marketing team is using Claude AI to replace 95% of their manual workload.

Connect with Rod Khleif:

Website: http://Rodkhleif.com

Podcast: Lifetime Cash Flow Through Real Estate Investing

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

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

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

Join us at The STR AI Summit is June 23-24 at the Freedom Factory in Beverly, MA.

100 seats only. Grab your ticket: https://www.strsecrets.com/aisummit

Most STR operators have built a great lifestyle business. But here's the hard truth: only 1 in 10 businesses will ever successfully sell. The rest close and walk away with nothing.

In this Portfolio Clinic training, Mike Sjogren breaks down exactly how STR management companies are valued — and what operators need to start doing right now to build a business with a real exit strategy.

He walks through the EBITDA formula, the exact valuation metrics used by C2G Advisors (the top M&A firm in the STR industry), why rental arbitrage and co-hosting businesses get little to no value from buyers, and why private equity has been quietly acquiring STR management companies since 2022.

He also introduces the Freedom Collective — STR Secrets' own roll-up model designed to give operators a share of the upside instead of selling to private equity at a discount. And he breaks down how AI agents can automate an entire acquisition pipeline from property data scraping to sales call booking.

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

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

She thought it had to be one or the other.

Career or kids. No middle ground.

Then her daughter was diagnosed with leukemia at three years old.

And everything changed.

Jane Ng left corporate America to care for her daughter full time. Her daughter survived — but was left with a brain injury that means she will never be fully independent. Jane will care for her for the rest of her life.

So going back to a W2 was never an option.

Instead she found real estate. Then short term rentals. Then co-hosting. Then a coaching business helping other moms do the same thing.

Today she owns 4 STRs, co-hosts 11 properties, runs a coaching business — and is home every single day for her kids.

Here's what she shared in this episode:

→ How she bought her first out-of-state property for $50K while parked on the side of a road in New Orleans

→ Why STRs are one of the most powerful tax savings tools for stay-at-home parents

→ How she built a team that runs the whole operation — with just one weekly check-in call

→ How she structures her week so she is never tied to her phone

→ The mindset shift that stopped her from quitting when things got hard

→ How she uses AI to find her next STR market before she even talks to a realtor

→ Why hospitality — not just for guests but for cleaners, neighbors, and vendors — is her #1 secret

This episode is for every mom who thinks she has to choose.

She doesn't.

Connect with Jane:

Instagram: @theinvestingmom

YouTube: @theinvestingmom

Connect with us:

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 - Intro

4:10 - Introducing Jane Ng: The Investing Mom

4:42 - How Jane's Daughter's Diagnosis Changed Her Life Forever

6:21 - Why Going Back to a W2 Was Never an Option

7:03 - Parked on the Side of a Road in New Orleans: The Moment Everything Changed

8:20 - From Long-Term Rentals to STRs: The 1031 Exchange That Started It All

9:18 - Why Her Daughter's Illness Made Her Braver in Business

11:39 - The Middle Ground: How STRs Let Her Be a Mom and an Operator

13:28 - The Identity Guilt That Holds Moms Back — and How to Get Past It

15:10 - Her Morning Routine: Up at 5:30, Kids First, Business Second

18:01 - Portfolio Overview: 4 Owned STRs, 11 Co-Hosted Properties, 3 Businesses

18:25 - Why the STR Tax Loophole Is a Game Changer for Stay-at-Home Parents

20:32 - How Co-Hosting Started: She Said No 6 Times Before Saying Yes

22:06 - How She Built Her Social Presence as a Self-Described Introvert

25:49 - How She Manages Everything: VA Structure, Weekly Check-Ins and Time Blocking

28:07 - How She Structures Her Week to Never Feel Tied to Her Phone

31:07 - Start Small: How to Build Good Habits Without Overwhelming Yourself

36:46 - How She Uses AI to Find Her Next STR Market

39:19 - Her #1 Secret to STR Success: Hospitality for Everyone

📲 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

Most luxury STR owners write that electric bill every month without ever knowing what's causing it. David VanWert did the same thing — until he built a platform to fix it.

In this episode, E and Chris sit down with David VanWert, founder of Umbra and owner of seven STR cabins in the Smoky Mountains and Mammoth Lakes. David built Umbra after spending years watching energy costs silently destroy the profitability of high-end vacation rentals — and after realizing no existing solution was built for the STR world.

In this episode David covers:

- What Umbra does: smart power monitoring and automation built specifically for large luxury STRs

- How Umbra integrates with your PMS to automatically cut power when guests check out

- Real results: 45% reduction in electricity cost per night, $620 saved in one month on one property, 30% lower bill YoY

- How silent system failures — clogged AC units, water leaks, tripped breakers — get caught before they become emergencies

- Why electricity costs in the Smoky Mountains regularly hit $2,000-$3,000 per cabin in winter — and how to stop that

- How David scaled to seven properties in under five years using second home loans, cost segregation studies, and the STR tax loophole

- Why the STR tax play — not cash flow — is the real opportunity for high-income earners buying right now

- David's full AI workflow: how he rebuilt his entire business from the ground up using Claude

- How he cut a 100-hour design project down to under 20 hours with AI

- Why he believes operators have a 4-6 year window to get ahead of AI before things get "weird"

- The time study method: how to audit every 15-minute block of your day and identify what AI can automate

- What happens to property managers and co-hosts when AI agents handle all communications, scheduling, and pricing

- David's #1 secret to STR success: tenacity

This is a rare conversation — equal parts operations, tech, and honest truth about where this industry is headed.

---

About David VanWert:

David VanWert is the founder of Umbra, a power-monitoring and automation platform built specifically for large luxury short-term rentals. He owns seven cabins — six in the Smoky Mountains and one in Mammoth Lakes — and built Umbra after experiencing firsthand how much energy waste and property risk goes undetected in high-end vacation rentals. His background is in technology and design, and he now splits his time between operating his own portfolio and helping other owners and property managers answer one simple question: what's running right now, and should it be?

Connect with David and Umbra:

Website: umbra-energy.com

Instagram: @umbraenergy

Facebook: Umbra Energy

Timestamps:

0:00 - Intro

1:22 - Introducing David VanWert and Umbra

5:28 - E's Michelin Restaurant Story: Service Is Black and White, Hospitality Is Color

9:06 - What Is Umbra and Why Did David Build It?

10:58 - The Real Cost of Running a Luxury STR: $2,000-$3,000 Electric Bills in the Smokies

12:49 - How Umbra Works: Smart Power Automation Tied to Your PMS

14:34 - Real Results: 45% Reduction, $620 Saved in One Month

16:37 - How Umbra Catches Silent Failures Before They Become Emergencies

18:34 - David's Background: From High-End Home Automation to STR Investor

20:26 - How David Scaled to Seven Properties in Under Five Years

21:58 - The STR Tax Play: Why High-Income Earners Should Be Buying Right Now

24:30 - Is the STR Market Still Worth It? What David Is Seeing Today

27:46 - How David Rebuilt His Entire Workflow Using Claude and AI

33:25 - From 100 Hours to 20: How AI Changed His Design Business

40:13 - The 4-6 Year Window: Why You Need to Get Ahead of AI Right Now

43:11 - What Happens to Property Managers When AI Handles Everything?

45:00 - Where to Start With AI If You Have No Tech Background

47:26 - David's #1 Secret to STR Success: Tenacity

If you haven't updated your pricing yet — your next booking will pay you less than you expect.

Btw you can grab the spreadsheet from here : https://www.strsecrets.com/airbnbfee

Also, if you want to talk to us directly: http://strsecrets.com/implement

In this training Mike covers:

- What the Airbnb fee change actually means: 15.5% host-only fee applies to nightly rate, cleaning fee, resort fee, pet fee — everything

- Why the split fee showing back up in your account is a bug — not a reversal

- The exact price increase you need to make: 18.34% minimum for direct owners

- How co-hosts and property managers need to handle this differently — and why checking the listing owner's account first matters

- The fee change spreadsheet walkthrough — how to model the right scenario for your business (comment FEE CHANGE to get it)

- How to split the channel fee with your homeowner so nobody loses

- How to track your Airbnb algorithm ranking after raising prices using Rank Breeze

- Why five-star properties make 18% more in RevPAR than 4.7-star properties — and how that matters more right now

- How Mike's portfolio is pacing 130% of June goals and 120% of July goals — and why

- Why now is the time to get on Vrbo — Mike is seeing 10% more bookings YoY from Vrbo this year

- How to retarget past guests with text messages and automated campaigns to offset any Airbnb drop

- Listing optimization basics: why your first five photos, your copy, and your reviews are your most valuable assets right now

This is the most important training for STR operators this month.

📲 Connect with STR Secrets:

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 - What Just Happened: Airbnb's Fee Change Explained

1:16 - The Split Fee Is Not Back — It Was a Bug

2:23 - What 15.5% Host-Only Fee Actually Means for Your Payout

3:04 - Step 1: Increase Your Airbnb Pricing by 18.34% Right Now

4:27 - Step 2: Track Your Algorithm Ranking After Raising Prices

5:44 - How to Check and Confirm Your Fee Setting in Airbnb

8:21 - The Fee Change Spreadsheet Walkthrough

12:30 - How to Split the Channel Fee With Your Homeowner

14:26 - What Co-Hosts and Property Managers Need to Do Differently

15:12 - How to Make Pricing Changes Inside Your PMS

16:03 - Testing Price Increases: 15% vs 18% vs 25% — What We've Seen

18:01 - The Airbnb Algorithm: What Actually Moves Your Ranking

18:25 - Five-Star Properties Make 18% More in RevPAR

19:48 - Virtual Stays, Friends and Family Reviews and Algorithm Boosts

20:15 - Mike's Portfolio Is Pacing 130% of June Goals — Here's Why

21:03 - Get on Vrbo: Mike Is Up 10% YoY From Vrbo This Year

22:15 - Retarget Past Guests With Text Campaigns Right Now

23:45 - Listing Optimization Basics: Photos, Copy and Reviews

24:07 - Action Steps and Where to Get the Spreadsheet

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

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

E just got back from the Unreasonable Hospitality Summit in Nashville — and this solo episode is his full recap.

Will Guidara wrote Unreasonable Hospitality during COVID. He took Eleven Madison Park from a nice restaurant to the #1 restaurant in the world — the only restaurant to ever go from one Michelin star to three in a single year.

His philosophy: service is what you do for people. Hospitality is how you make them feel.

In this episode E breaks down the biggest lessons from the summit — how to systematize hospitality so your team delivers it consistently, why hiring the person over the resume matters more than you think, how to build a culture of praise and feedback that makes teams want to grow, and why the magic moments your guests remember are never accidental.

He also tackles the AI question head on: the answer is not cutting your team — it is repurposing them to create more human moments in a world where genuine connection is becoming a scarce resource.

The episode closes with the question Will Guidara asked the room that E says called him to greatness: "What would you attempt to do if you knew you couldn't fail?"

Get the book: Unreasonable Hospitality by Will Guidara

New book: Unreasonable Hospitality Field Guide (released April 28, 2026)

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

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

In 2016, Cara and Mark Truckey lost their 14-month-old son. He never woke up at daycare.

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 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

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 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

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 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

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

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

Resources mentioned in this episode are available at: strsecrets.com/clinic

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

YOUTUBE DESCRIPTION

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?"

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

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

Connect with Sean:

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

Connect with Jeremiah:

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

Scaling a short-term rental company isn’t just about getting more properties.

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

Want the resources mentioned in the training?

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

He built a “sexy” real estate portfolio in the early 2000s…

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

2026 is going to separate serious operators from everyone else.

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/

Most entrepreneurs think they need better strategy.

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/

Vivian Yip went from corporate burnout at Apple to building a thriving midterm rental portfolio and property management company.

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/

Most STR hosts misunderstand influencer marketing — and it’s costing them bookings.

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/

Success in STR isn’t about age, capital, or the model you choose — it’s about conviction.

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/

The STR market isn’t crashing — it’s recalibrating.

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/

Scaling isn’t a systems problem — it’s a leadership problem.

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/

Most operators think better tech will fix their problems. It won’t.

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/

Your goals aren’t failing — your calendar is.

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/

The STR game has changed—and most operators haven’t caught up.

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/

Most people don’t fail because they lack discipline — they fail because they’re trying to grow without changing who they are.

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/

Most entrepreneurs focus on tactics — but the real breakthroughs happen internally first.

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/

AI isn’t a tool anymore — it’s infrastructure.

In this episode, Chris and E sit down with Shahar Goldboim, founder of BOOM, to break down how AI is fundamentally changing short-term rental operations, exits, and scale.

From selling a property management company to building tech that replaces broken workflows, this conversation dives deep into why fragmented tools are failing and why operators who don’t adapt will fall behind.

Inside this episode:

• Why “tech-enabled” STR businesses still fail
• The biggest mistakes operators make when exiting
• Why one company can’t do funds, PM, design, and tech well
• How AI eliminates 80% of guest 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/

Your STR isn’t underperforming by accident — it’s underperforming because of decisions.

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/

Your business can’t outgrow the identity you’re stuck in.

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/

The arbitrage era is cracking — fast. 

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/

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

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

Inside this episode:

• Why most PMs never break past 50–100 properties

• The REAL reason owner acquisition is so difficult

• Brooke’s formula for predictable PM growth

• Why marketing is now non-negotiable for property managers

• What the top PMs are doing differently

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

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

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

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

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

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

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

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

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

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

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

Guest Bio:

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

Guest Link:

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

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

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

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

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

In this episode you’ll learn:

• Why your STR business already has real enterprise value

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

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

• How to build systems that survive without you

• What buyers REALLY look for in an STR business

• The path to a 7–8 figure STR exit

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

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

00:01:41 - Sonder going bankrupt

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

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

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

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

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

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

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

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

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

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



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

• The story behind building the Freedom Factory

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

• The dark seasons every entrepreneur must push through

• Why property management will create more millionaires than arbitrage

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

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

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

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

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

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

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

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

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

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

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

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

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

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



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

• How AI is transforming pricing, operations, and marketing

• The biggest mistake hosts make when “trying” automation

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

• Why your business model must evolve in 2025

• The new advantage: data-driven decision-making

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

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

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

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

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

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

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

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

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

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

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

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

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

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

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

• How to make decisions from faith, not fear

• The identity → behavior → reality chain

• Why discipline is just choosing desire repeatedly

• What to do when growth feels uncomfortable

• How your environment can hold you back

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

00:00:12 – Paradigm = Fear and Lack

00:01:44 – Choosing to Live From Desire

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

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

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

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

00:10:12 – Growth Requires Discomfort

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

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

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/