Short Term Rental Secrets Podcast

What is your short term rental management company actually worth? Jacobie Olin sells these companies for a living, around 20 deals a year worth close to 200 million dollars, and in this episode he breaks down exactly how buyers value your business, what multiples they pay, and why most operators are sitting on a lifestyle business instead of a sellable asset.

Jacobie is the founder of C2G Advisors and brokered the landmark Vacasa and Casago deal. He walks through EBITDA, multiples, take rate, churn, and the real steps to turn a small management business into something worth millions. If you have ever thought about selling your rental business one day, this is the playbook for what to build toward now.

TIMESTAMPS

00:00 Meet the man who brokers STR company sales

00:25 What C2G does and the size of deals they run

02:25 Inside the Vacasa and Casago deal

09:10 Why big money is moving into a fragmented industry

10:32 The state of the market and why the next few years favor sellers

13:30 How companies are valued by size (the multiple ladder)

16:00 Why smaller deals pay you less cash up front

17:56 Turning a lifestyle business into a sellable asset

21:00 The magic number that opens the door to real buyers

24:35 Can you sell on co-host contracts instead of full management?

26:35 Mike Reilly asks: how do I acquire another company?

32:45 The KPIs that actually drive your valuation

41:12 The fee trick that quietly raises your take rate

42:45 Where the whole industry is headed next

Want the KPI scorecard from this episode? DM @strsecrets on Instagram.

Learn more about C2G Advisors: https://c2gadvisors.com

Connect with Jacobie: [email protected]

Subscribe for new episodes every Monday.

#ShortTermRentals #PropertyManagement #AirbnbHost #VacationRentals #STRSecrets #RealEstateInvesting #BusinessExit #MergersAndAcquisitions

Everyone in short-term rentals is chasing the next tool.

The next software. The next tech company. The next shiny object.

Jason Muth did the opposite. And it built him a 53-unit business in about two years.

In this episode, Jason joins the show to break down how he grew Prideaway Stays from his first client in April 2024 to 53 properties under management, with zero acquisitions and 100 percent organic growth.

No buying other companies. No chasing every new tactic. Just one market, one avatar, and a relentless focus most operators are too distracted to hold.

In this episode:

→ Why Jason picked one town, went all in, and refused to look at a single other market

→ The organic growth engine behind 53 units, from handwritten direct mail to referrals from cleaners and owners

→ How he walked away from a career at some of the biggest media companies in the country and became the go-to short-term rental expert in his market

→ The delegation moment on a cruise that finally forced him to stop doing everything himself

→ How he educates owners with simple monthly videos and real data, and why that consistency builds trust that closes deals

→ Why the market has shifted, how property values doubled while revenue did not, and what that means for owners today

→ His number one secret to success: make big decisions fast, and stop chasing shiny objects

If you feel overwhelmed by every new tool and tactic in this space, this episode is the reset you need.

About Jason:

Jason Muth left W-2 life in 2022, after his real estate side hustle became more profitable than his corporate career at companies like Comcast, NBCUniversal, and iHeartMedia. He is the founder of Prideaway Stays, a boutique, gay-owned, tech-driven co-hosting business in Provincetown, MA, and the owner of Straightforward Short-Term Rentals in Massachusetts and New Hampshire. He also hosts the SmartStay Show.

Connect with Jason:

Instagram: @prideawaystays

Podcast: SmartStay Show, on YouTube, Spotify, and Apple Podcasts

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

Most operators grow their rental business one contract at a time. Cameron Masters skipped the line and bought his way from 18 units to over 140 in a single deal.

In this episode, we sat down with Cam to walk through the whole acquisition, start to finish. He bought a 40 year old management company, one started by a founder of Vrbo, and he shares the exact moves that got it done.

Inside this episode:

How Cam went from 18 units to 140 plus by buying one company

Why he skipped the bank and used seller financing plus a friends and family raise

How he and his partner put in just 30 percent and got the seller to carry the rest

The 10,000 dollar move that can save you from a 1 million dollar mistake

The 35,000 dollar cost he forgot to check, and how it bit him after closing

The room full of bigger operators that made him stop thinking small

If you have ever felt like real growth is out of reach, this one will change how you think about what is possible.

Want to be in the room with operators doing deals like this? Check out the STR Secrets Mastermind: strsecrets.com/apply

Connect with Cameron Masters on Instagram: @cameron.masters_

New episodes every Monday.

Want to scale your property management or co-hosting business past 10, 20, 50 listings? Book a call here: https://strsecrets.com/apply

Connect with Mike Reilly : https://www.instagram.com/mikereillync/

Most operators think busy season is the worst time to look for new properties. Mike Reilly just signed 7 new contracts that prove them wrong.

Last quarter his team at NC Stays reached out to 1,000 homeowners. They opened 68 real conversations. They signed 7 new properties, and 19 more deals are still on the table. And all of it started in the middle of peak season.

Why? Because of one thing most operators never check: the 90 day notice window. Most management contracts renew in the fall. If a homeowner wants to leave their property manager, they have to say so 90 days before the contract renews. So if you wait until September to start talking to owners, they're already stuck for another year.

In this 18 minute training, Mike walks through his COHOST funnel step by step:

C: Create awareness. A simple website, social posts, and a list of homes you want.

O: Open the conversation. Send a free 5 minute video showing the owner what they're missing. Don't ask for a meeting.

H: Hold the discovery call. This is where deals are really won, and where you filter out bad-fit owners.

O: Offer your solution.

S: Sign the contract. Including the $2,500 upgrade rule Mike puts in every contract.

T: Take over and onboard. This pairs with last week's onboarding episode.

Plus the story of a beach house owner losing $30,000 to $40,000 a year because his best photo was buried at spot #68 in his listing. And why it takes about 4.5 calls before an owner signs.

If you have no new leads right now, this episode shows you why. Save it.

Want the owner contact lists, the CRM, and a community of operators growing past 50 listings? Check out the STR Secrets Mastermind: [LINK]

New episodes every Monday.

Want to scale your property management or co-hosting business past 10, 20, 50 listings? Book a call here: https://strsecrets.com/apply

Connect with Mike Reilly : https://www.instagram.com/mikereillync/

How do you onboard 7 vacation rental properties in one month without burning out your team?

Mike Reilly breaks down the exact 6 stage onboarding system NC Stays uses for every new property, from the first homeowner call to the post launch celebration.

Homeowner trust in property managers is at an all time low.

Nearly every owner has been burned before.

The managers who onboard properties with a real system are locking in 5 to 10 year relationships and standing out in a market flooded with new co-hosts.

In this training you'll learn the full checklist:

• Why the first 30 days with a homeowner decides the next 10 years
• The 6 stages of onboarding: Handoff, On-Site Setup, Photography, Listing & Software Setup, Final Touches, and Post Launch
• How Mike's team uses Meta glasses to capture every inch of a home and turn it into checklists automatically
• The QR code trick that eliminates guest questions about the grill, hot tub, sauna, and game room
• The exact roles to hire: project manager, contractor help, listing team, and data quality
• How one Pinehurst property pulled $30,000 in bookings from mood boards alone, before it was even ready
• The review stay strategy that gets Airbnb pushing your listing to page one in week one

TIMESTAMPS

00:00 Trailer

00:37 Welcome back + what's coming for the podcast

02:02 Onboarding 7 properties in one month (all 4,000+ sq ft)

03:59 The trust crisis and why onboarding is your biggest advantage

05:00 The system and the 6 roles you need on your team

07:58 The 6 stages of onboarding explained

08:01 Stage 1: The Handoff (welcome email, onboarding form, group text)

09:55 Stage 2: On-Site Setup with Meta glasses

11:12 QR codes, inventory counts, and the house manual

14:30 Stage 3: Photography (lifestyle shots, staging, shot lists)

15:35 Stage 4: Listing & Software Setup (custom GPT listings, PriceLabs)

16:55 $30,000 in bookings from mood boards before launch

17:36 Stage 5: Final Touches (data quality, review stays, financials)

19:07 Stage 6: Post Launch (social posts, email list, owner shareables)

20:02 Why you can't scale without this process

20:41 Inside the STR Secrets Mastermind

Something big is happening in short-term rentals, and most operators have

no idea.

In this episode, Mike Sjogren returns to the show with Mike Reilly. And they open with a

trend that changes everything.

In 2022, most short-term rentals in the US were run by hosts with fewer than 20 units. By 2025, that share had dropped hard. The reason is not that hosts quit. It is that private equity quietly started buying up management companies, because the margins are good and the industry is wide open.

Mike breaks down what that means for you, and reveals the project STR Secrets has spent 16 months building to help members cash in on it.

In this episode:

→ The data behind the great short-term rental consolidation, and why the big money is moving in now

→ Freedom Collective: the new vehicle built to help operators sell their management company for a 6 to 8X exit instead of a 3 to 5X

→ How 22 members generated over $3 million in new management commissions in about 7 weeks, including one who acquired a company and added 122 doors in a single quarter

→ The full AI Summit recap

→ Why the most important hire of the next few years is an AI mplementation specialist, and why the CEO's job is to cast the vision, not tinker in the tools until 3am

→ Mike's own Q2 numbers from the new AI-powered CRM: 1,000 leads, 68 opportunities, 7 new clients, and $211,000 in new commissions, while taking only 10 percent of the sales calls himself

Whether you have your first property or your fiftieth, this episode will change how you think about where this industry is headed.

Ready to scale and exit the right way? Apply to work with us: strsecrets.com/apply

Six years ago, E said yes to something he had no idea would change his life.

300 episodes later, this is his last one.

In this final solo show, recorded from his grandparents' house in Sardinia, Emanuele Pani answers the same question this podcast has asked every guest for six years.

What is your number one secret to success?

Only this time, he answers it for himself.

E shares the 5 lessons that changed his life more than anything else.

The lessons that took him from chasing more information, more courses, and more outside validation, to the most peace, health, and happiness he has ever felt.

In this episode:

→ Why your identity, not your strategy, decides how far you go

→ The difference between goals and standards, and why standards are the ones that actually shape your future

→ How the story you tell about yourself becomes the life you live

→ Why every level of growth costs you the person you used to be

→ The inside-out truth about success that no system or strategy can replace

This is not a goodbye.

It is a thank you to a community that has spent six years in E's ears.

In your cars. In your kitchens. On your morning walks.

And it is a torch being passed.

Thank you for everything, E.

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

Join the community: STR Secrets Facebook Group

You can follow E's next chapter on his new show, CEO Mindset, available

now on Spotify and Apple Podcasts.

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 own company into Five Star Vacation Home Rentals, where he now owns the San Antonio division, part of a portfolio of 70 properties across Central Texas. And he finally walked away from nursing for good.

Today, based in San Antonio, Texas, Jeremy focuses on revenue optimization, guest experience, property operations, and scaling high performing vacation rental portfolios.

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 figureoutable" 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.

Connect with Jeremy:

Instagram and Facebook: @fivestarvhr

Email: [email protected]

Website: fivestarvhr.com

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"