Short Term Rental Secrets Podcast

Latest Episodes:

Ep 256 - Why 95% of STR Deals Fail—and the 10 Hospitality Rules That Make the Rest Win Aug 25, 2025

Show notes

Most STR deals fail before they even start—95% don’t pencil out.

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

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

• 10-point hospitality playbook

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

• The creative edge investors need to make deals work

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

• How to balance ROI with guest delight and repeat bookings

00:03:56 – Service vs. Hospitality

00:06:11 – Setting Higher Financial Targets

00:08:09 – Guest Experience at Every Stay

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

00:16:23 – Guest-Centric Business Model

00:17:17 – Scaling Means Scaling Leadership

00:20:27 – The Roots of Modern Hospitality

00:22:52 – Designing Emotional Guest Checkpoints

Get FREE Access to our Community and Weekly Trainings:

http://group.strsecrets.com/

Ep 255 - How Two Investors Scaled from Co-Living to 80 STRs with Blake Anthony Carter and Jeremy Courtney Aug 18, 2025

Show notes

Blake and Jeremy went from managing shared co-living spaces to running 80 short-term rental properties.

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

• How they pivoted from co-living to STRs

• The growth path from a handful of units to 80

• Systems they rely on to keep operations tight

• The partnerships that accelerated their scale

• Lessons learned about market selection and timing

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

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

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

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

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

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

00:18:59 - Identifying problems and fixing them

00:20:48 - Preventing issues from stacking up

00:23:39 - Taking responsibility for team mistakes

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

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

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

00:37:18 - Challenges get easier with experience

Guest Bio:

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

Guest Link:

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

https://www.instagram.com/thejeremycourtney

Get FREE Access to our Community and Weekly Trainings:

http://group.strsecrets.com/

What It Really Takes to Run a Top STR Management Company | The STR Scale Show with Mike Reilly | Ep 24 Aug 14, 2025

Show notes

Being the #1 property manager in the U.S. isn’t all glamour—it’s grind.

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

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

• The workload reality behind rapid STR growth

• Why work-life balance is elusive in property management

• How to keep guest satisfaction high while scaling

• Lessons on building a sustainable management model

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

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

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

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

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

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

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

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

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

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

00:16:37 - Seasonality or Demand Shifts

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

00:22:04 - Pricing Tactics to Drive Occupancy

00:24:40 - Market Share / Portfolio Size

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

Get FREE Access to our Community and Weekly Trainings:

http://group.strsecrets.com/

Ep 254 - How to Buy Back Your Time and Scale Your STR Business Faster Aug 11, 2025

Show notes

Most STR owners get stuck putting out fires instead of building the business they actually want.

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

• Why you always need that next big goal

• The real reason we become entrepreneurs: time control

• How to qualify and hire your first key player

• Setting up turnover checklists that run without you

• The role that keeps properties guest-ready every day

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

• The investment that buys back your time

• How to stop micromanaging and reacting to fires

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

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

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

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

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

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

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

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

Get FREE Access to our Community and Weekly Trainings:

http://group.strsecrets.com/

What You Actually Missed at STR WealthCon (and Why It Matters for STRs) | The STR Scale Show with Mike Reilly | Ep 23 Aug 07, 2025

Show notes

This episode is a behind-the-scenes look at the latest STR WealthCon.

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

• Why raw content works better than polished

• The one onboarding question that reveals true goals

• STR WealthCon recap: biggest takeaways

• How to get ROI from live events

• The vibe shift in the STR community

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

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

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

00:03:01 - Raw Content That Converts

00:05:55 - Massive Takeaways From WealthCon

00:08:42 - Unlock Event ROI Secrets

00:11:32- Mindset Shift Every Host Needs

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

00:16:54- High-Impact Networking Tips

00:19:32- Underrated Gold From Live Events

00:22:21 - Mastering the Referral Flywheel

00:25:06- Growth Hacks for Ambitious Hosts

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

Ep 253 -The Architecture of Living: Why Design Should Fit Your Real Life with Zeke Freeman Aug 04, 2025

Show notes

Most homes look good on paper.

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

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

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

What you’ll learn:

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

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

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

- Why your home may be sending the wrong emotional signals

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

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

00:04:32 - Why Architects Make Great Entrepreneurs

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

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

00:14:06 - Designing Offers Like Floor Plans

00:17:21 - Why Constraints Fuel Creativity

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

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

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

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

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

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

Guest Bio:

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

Guest Link:

https://linktr.ee/zfreeman1

Get FREE Access to our Community and Weekly Trainings:

http://group.strsecrets.com/

Ep 252 - The 5 Sales Principles Every STR Closer Needs to Master with Adam Stein Jul 28, 2025

Show notes

If you want to win in cohosting, you need to sell.

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

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

What You’ll Learn:

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

Guest Bio:

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

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

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

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

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

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

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

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

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

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

Guest Link:

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

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

Most STRs Fail Because They Cut Corners (Here’s the Math) | The STR Scale Show with Mike Reilly | Ep 22 Jul 24, 2025

Show notes

Most people lose in STR because they think small.

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

You’ll learn:

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

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

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

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

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

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

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

Want bookings before you're even done renovating?

Just click the link below to get the Free Training.

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

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

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

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

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

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

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

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

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

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

Ep 251 - The Airbnb Roll-Up Strategy No One’s Talking About with Patryk Swietek Jul 21, 2025

Show notes

He’s not managing Airbnbs, he’s buying the companies that do.

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

You’ll learn:

• How to value STR property management companies

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Guest Bio:

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

Guest Link:

https://www.instagram.com/patryk_swietek

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

The Tax Loophole That Can Wipe Out $40K (Even With 1 Property) | The STR Scale Show with Mike Reilly | Ep 21 Jul 17, 2025

Show notes

The new Trump-era bill just brought back 100% bonus depreciation and STR owners are about to get a massive tax break.

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

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

You’ll Learn:

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

• The 2 conditions to qualify for non-passive treatment

• How cost segregation studies supercharge your deductions

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

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

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

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

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

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

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