Short Term Rental Secrets Podcast

Latest Episodes:

Ep 245 - From Tragedy to Terra: How Diana & Josh Built Palm Springs’ First Wellness Hotel Jun 09, 2025

Show notes

This episode is a masterclass in turning pain into purpose.

Diana and Josh, two married architects, were forced to reimagine their future after losing both their fathers in 2021.

What began as a journey to escape the W-2 grind became Terra Palm Springs, the city’s first true wellness boutique hotel.

They reveal how they:

• Pivoted from flips and BRRRRs into commercial real estate

• Used their design and construction edge to underwrite with vision

• Created immersive guest experiences that transcend hospitality

• Built three synergistic businesses to scale with intention

• Took bold action while honoring their deepest personal “why”

This story will move you, inspire you, and give you a real blueprint for building a brand, and a life that matters.

What You’ll Learn:

• How to spot your unfair advantage (and actually use it)

• The key to underwriting without inflating projections

• What makes a boutique hotel truly stand out

• How to transition from short-term rentals to hotel ownership

• Why generosity is the secret weapon in hospitality

00:00 - Action drives clarity

00:35 - Process-proven growth

01:36 - Power couple feature

02:20 - Life-changing loss

05:55 - Strategic shift to scale

07:26 - Expert system builders

09:50 - Value-add obsession

10:56 - Underwrite with confidence

14:30 - Unapologetic branding

16:42 - First-of-its-kind wellness hotel

21:00 - Team-powered execution

25:40 - The real estate awakening

28:00 - Finding purpose through pain

31:30 - Create your unfair advantage

36:00 - Future-built freedom

43:00 - Hospitality secret: give generously

Guest Bio:

Diana and Josh Dobken have 15+ years of experience in the architecture and construction industries. They strategically invest in value-add opportunities where they can use their design expertise to maximize their return on investment. Additionally, Diana and Josh co-host 35+ MTRs and STRs across multiple states for other real estate investors, bringing their hospitality standards and design sensibility to each property we manage.

Beyond property investment, Diana and Josh also manage comprehensive operations teams for hotels, with them overseeing director of operations roles and guest experience management. This hands-on operational experience gives them invaluable insights into how design decisions impact day-to-day functionality and guest satisfaction.

Their most current project involves the Architectural and Interior design of Terra Palm Springs, the first wellness Boutique Hotel in Palm Springs featured in Vogue, Forbes, Hotels Above Par, and selected as part of Travel and Leisure It List of 2025’ 100 Best New Hotels in the World.

Guest Link:

http://www.instagram.com/d.i.fi

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

AirDNA’s New Tools Just Gave Smart Hosts a Huge Advantage (Here’s What to Do) | The STR Scale Show with Mike Reilly | Ep 15 Jun 05, 2025

Show notes

AirDNA just dropped its biggest platform update in years, and if you’re not using these tools, you’re falling behind.

From custom comps to Airbnb integration, this episode breaks down the new features, how to use them, and what they reveal about the 2025 STR landscape.

What you’ll learn:

How to use the new Rentalizer confidence score and custom comps
Why saved projections and expense tracking are game changers
The truth about 2025 booking trends (and who’s winning)
What AirDNA’s forecast says about rates, RevPAR, and smart investing

If you’re serious about short-term rentals, you can’t afford to miss this.

Want to get our Latest Deal Analyzer?

Just click the link to our Instagram below and send 'Rentalizer'

https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T015&utm_content=Rentalizer

02:35 – Why the Update Matters: Major Interface and Logic Changes

05:10 – Data Model Shift: From Historical to Projected Revenue

08:00 – The 3 Core Metrics You MUST Understand in the New Version

11:00 – Updated Filters: Comp Selection and Market Targeting

13:30 – Accuracy Considerations: What AirDNA Gets Wrong (and Right)

16:45 – Real-Time Demo: Using the New Tool to Analyze a Property

20:20 – How to Reverse Engineer a Successful STR Deal with AirDNA

24:00 – Hidden Pitfalls: Common Mistakes People Make Post-Update

28:10 – Strategic Recommendations for Using the New Rentalizer

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

Ep 244 - From Banking to 96 STRs: Why Fouad Built a Bankable Airbnb Empire Jun 02, 2025

Show notes

Fouad spent 20 years in banking and 11 more consulting banks before walking away from corporate life when his wife’s income surpassed his.

What happened next?

A wild ride through the world of short-term rentals, driven by family, strategy, and a long-term vision few operators ever reach.

In this episode, Fouad breaks down:

How a personal medical emergency forced him to buy his first Airbnb
Why most operators price listings wrong—and how he uses math instead
The real difference between luxury and comfort STRs (and why he runs both)
His custom tech stack using Go High Level
And the real reason he’s scaling to $12M/year before exiting

This one’s for the operators who want to scale smart, stay profitable, and build something sellable.

What you’ll learn:

How to scale with dual verticals (luxury + comfort)
Why you must reverse-engineer around your exit
How banking lessons apply directly to STRs
Why pricing = math, not emotion
How Fouad thinks about purpose and legacy

Ready to build a business that banks would beg to fund?

Fouad shows you how.

03:30 – Breaking the Golden Handcuffs: Why He Left Corporate

07:00 – First STR Deal: Starting Small With Big Vision

10:00 – Smart Risk: Learning to Bet on Yourself

13:00 – From 1 to 10+ Units: Scaling With Confidence

17:00 – Wealth Mindset: Thinking Like an Owner, Not an Operator

20:00 – Cash Flow vs Time: Redefining Success Metrics

24:00 – Building a Business, Not a Job: Systems and Team Growth

27:00 – Lessons From the Field: What He’d Do Differently

30:00 – Purpose-Driven Investing: Time, Family, and Freedom

Guest Bio:

Fouad Bazzi is a professional in the short-term rental (STR) industry. His activities include owning, managing, and building new build-to-rent properties, as well as consulting and educating others in the STR space. He also owns a pool servicing company that specializes in serving STR properties.

Guest Link:

https://www.instagram.com/fouad_airbnb

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

Airbnb Summer 2025 Update: What Hosts Need to Know About Services & Experiences | The STR Scale Show with Mike Reilly | Ep 14 May 29, 2025

Show notes

Airbnb just rolled out its biggest update of the year, and if you’re a host, you need to know what’s coming.

In this live breakdown, we cover:

• The truth about Airbnb’s new “Services” feature and why it matters

• What this means for photographers, chefs, massage therapists, and YOU

• How Airbnb plans to monetize add-ons (and why you might not see a cut)

• Major liability concerns Airbnb isn’t talking about

• How this could affect your guest experience—and your reviews

• Why this is really a pivot toward becoming the Instagram of Travel

Plus: actionable strategies to get ahead of this change, build local service partnerships, and protect your property.

TLDR? This update means more work for hosts, unless Airbnb starts paying us to help them grow. Watch this now so you’re not caught off guard.

Want to get the summary of Airbnb's Latest Update?

Just click the link to our Instagram below and send 'Update'

https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T014&utm_content=Update

00:00 – Bold Shift: Airbnb’s 2025 Release Redefines the Platform

01:30 – Major Update 1: Cleaning Services Now Offered to Guests

04:00 – Major Update 2: Handy Services and Maintenance on Demand

06:30 – Control at Risk: Services Can Be Scheduled Without Host Approval

08:45 – Host Autonomy Undermined: Who Has Access to Your Property?

10:30 – Guest Experience Prioritized: Host Voice Being Muted

12:00 – Airbnb’s Strategic Shift: From Booking Site to Service Ecosystem

13:30 – Host Action Plan: Communicate, Audit, and Prepare

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

Ep 243 - From Zero to $1B: Hostaway CEO Marcus Rader on AI, Talent, and the Brutal Truth About Scaling May 26, 2025

Show notes

In this raw, no-fluff episode, Hostaway CEO Marcus Rader shares the hard-won lessons behind building a billion-dollar vacation rental software company, starting with zero industry experience.

Marcus breaks down:

Why most entrepreneurs aim too small and why it costs them everything
The mental and physical toll of building at scale (including 7 years without a dentist visit)
How he filters “good money” vs “bad money” when raising capital
The future of short-term rentals in a regulated, AI-powered world
Practical leadership advice for scaling teams without losing your mission

Plus: his marathon training, travel hacks, and how to avoid becoming a micromanaged founder.

Whether you’re a startup founder, STR operator, or tech junkie—this is a must-listen for anyone who wants to win big without burning out.

Ready to scale? Tap into Marcus’s billion-dollar playbook now.

00:00 – Go Bigger: Why Playing Small Carries the Same Risk but Less Reward

00:39 – Craft Over Hype: The Power of Repetition and Mastery

02:04 – Be There: Why Leading Remotely Doesn’t Win Markets

03:45 – Market Leadership: How Hostaway Beat Older, Bigger Players

05:58 – Hiring Giants: From 50,000 Applicants to the Top 0.1%

08:59 – Cost of Ambition: Health, Relationships, and the Real Price of Building

12:29 – Go for Billionaire Moves: Why Medium Goals Aren’t Worth the Sacrifice

15:31 – Choosing Good Money: Partnering with Investors Who Let You Lead

17:23 – No Kitchen Rules: Keeping Creative Control While Scaling Up

20:27 – Invisible AI: How Hostaway Uses Tech to Deliver Unseen Excellence

23:00 – Review Intelligence: Turning Guest Feedback into Business Strategy

25:30 – Tool Advantage: Hostaway’s Marketplace as a Growth Engine

27:17 – Global Expansion: Owning New Markets One Continent at a Time

29:33 – Regulation Shakeout: Why Strong Rules Are Good for Professionals

32:50 – Reputation Reset: Cleaning Up the Industry with Standards That Matter

Guest Bio:

Marcus Räder is co-founder and CEO of Hostaway, the leading all-in-one vacation rental management software. Originally from Finland, Marcus has lived in many countries around the world including Sweden, Poland, and The Netherlands before settling in Canada. It was this passion for travel, real estate and his dedication to learning about the vacation rental ecosystem that enabled the creation of Hostaway.

The company quickly grew thanks to the deep technological expertise of its founders, with over a decade of tech start-up success between them. Hostaway gives property managers all the tools needed to compete with hotels and other vacation rentals, including sales channel management, dynamic pricing and hospitality services. It now boasts preferred partnerships with Airbnb, Vrbo and Booking.com, in addition to a marketplace of over 100 integrated software partners.

Guest Link:

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

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

EP 242 - How AI & Leadership Are Scaling the Best STR Businesses in 2025 May 19, 2025

Show notes

This episode unpacks the real playbook behind scaling short-term rental businesses with AI, leadership, and culture.

Straight from the STR Boardroom event in Salem, hosts Chris and E break down their biggest takeaways from Dr. Rachel Gainsbrugh’s AI workshop to the emotional breakthroughs in hot seats, to Mark from Minoan’s CEO mindset at 50+ employees.

What you’ll learn:

• The AI stacking method Rachel used to double her sales team’s close rate

• The 5 levels of VA hiring, from cheap help to AI-powered specialists

• Why great team members outgrow companies, and how to lead through it

• The exact moment a founder must pivot from operator to people leader

• How to use the 5 Dysfunctions of a Team framework to build culture that scales

• Why emotional safety is the hidden growth lever most CEOs ignore

• And how to actually implement event takeaways before you lose momentum

This isn’t another tech tips episode.

It’s a tactical and vulnerable deep dive into what it takes to scale, lead, and stay grounded in 2025.

00:00 – Building Confidence: Lessons from Struggle, Sales, and Self-Belief

04:00 – Rewiring Identity: From Overwhelm to Intention

08:00 – Leveraging Chaos: Why Adversity Becomes Your Superpower

12:00 – The Four Levels of Competence: From Unconscious to Mastery

16:00 – Winning in Business: Simplifying Systems, Offers, and Time

20:00 – $20K Days in 5 Hours: Prioritizing High-Leverage Work

24:00 – Clarity Is Power: Why Lack of Decision-Making Kills Momentum

28:00 – Excuse Audit: The Hidden Stories That Keep You Small

32:00 – Emotional Regulation: How to Respond Instead of React

36:00 – Final Challenge: Step Into Power and Choose a New Story

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

Hiring a Virtual Assistant? Do NOT Skip This Step | The STR Scale Show with Mike Reilly | Ep 13 May 15, 2025

Show notes

Most people screw up VA hiring, not because they pick the wrong person…

…but because they don’t have a system.

In this training, Mike and Chris break down the 3 proven models for hiring virtual assistants.

Agency, recruiter, and self-hire.

Plus the crucial 4R framework you need before bringing anyone on.

Whether you’ve got 5 properties or 100+, this is the training that saves you from wasted money, broken systems, and constant turnover.

What you’ll learn:

• The 3 types of VA hiring models (and when to use each)

• The biggest reason your VA won’t work out (it’s not what you think)

• How to build a talent pipeline that scales with your portfolio

• When to hire for skills vs culture fit

• Bonus: Where to find agency + recruiting referrals we actually trust

Want to get the FREE VA Contract and 4R Doc?

Just click the link to our Instagram below and send 'Contract'

https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T013&utm_content=Contract

00:00 – Hiring Roadmap: Breaking Down the VA Models

02:00 – Agency Model Explained: Training Wheels for Scaling Leaders

05:00 – Recruiting Model: Upfront Investment, Long-Term Efficiency

08:30 – Self-Hiring Secrets: Full Control, High Risk, High Reward

11:00 – Referral Power: Leveraging A-Players to Source Talent

13:30 – Cultural Pitfalls: The Hidden Risk in Team Referrals

16:00 – Specialty Roles: Revenue Management vs. Marketing VAs

19:00 – Creating Execution Frameworks for Social & Brand Marketing

22:00 – Revenue Management Mastery: Metrics, Mindset, and Misconceptions

25:00 – Bonus Resource: Contract Templates & Legal Protections for VA Hiring

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

Ep 241 - The 5 Mindset Shifts That Changed Our Lives (And Can Change Yours) May 12, 2025

Show notes

Most people aren’t missing strategy.

They’re missing decision.

In this episode, Mike and Emanuele break down the 5 mindset philosophies that transformed their lives...

...from escaping burnout and W2 jobs to building multi-million-dollar businesses and raising families with time freedom.

If you feel like you keep “trying” but never break through, this episode will call you out...

...and pull you forward.

What you’ll learn:

The most powerful reframe for taking back control of your life
Why saying “I’ll try” guarantees failure
How to train your decision-making muscle daily
The “day one” philosophy that separates top performers from the rest
A no-fluff breakdown of time vs. money thinking (and how to escape the trap)

Ready to finally commit?

This is your line in the sand.

00:00 - Uncovering Transformational Beliefs that Redefined Success

04:00 - Embracing Radical Ownership: Life Happens *For* You

09:35 - Unlocking Growth Through the Day One Philosophy

14:30 - The 4 Powerful Stages of Skill Development

18:20 - Tactical Time vs Money: Rewriting Productivity Rules

22:00 - Designing a $20K Month in 5 Hours: The Value-Driven Hustle

26:30 - Eliminating Excuses: Breakthrough Decisions that Shape Destiny

31:10 - The Critical Power of Fast Decision-Making

33:00 - Rethinking Reality: Story, Meaning & Inner Peace

35:00 - Final Challenge: Cut the Dirty Yes, Choose Powerfully

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

7 Things Killing Your STR Reviews (And How to Fix Them Today) | The STR Scale Show with Mike Reilly | Ep 12 May 08, 2025

Show notes

Your property is great. So why are guests still leaving 4 stars?

In this episode, Mike breaks down the 7 most common mistakes that silently ruin guest experiences and the reviews that follow.

These aren’t theories.

They’re field-tested lessons from 1,200+ reviews, across 28 properties, and over 5 years of hosting.

You’ll learn:

Why nickel-and-diming your guests kills conversion
The #1 amenity guests expect (but almost no one provides)
How to stop losing stars from poor messaging and over-automation
Why Photoshop and misleading listings backfire (fast)
The deep clean schedule every top host follows
How to protect margins while leveling up experience
The review-killer most hosts don’t realize they’re doing

If you’re stuck at 4.8 and can’t crack 4.95+, this is your fix.

05:00 – Algorithm Boost: How Amenities and Photography Drive Ranking

06:00 – Lightning Response: The Profit Power of Immediate Communication

08:00 – Misleading Listings: The Hidden Cost of Photoshop and Fluffed Locations

11:00 – Guest-Friendly Pricing: Stop Nickel-and-Diming for Add-Ons

13:00 – Annual Investment Rule: Keeping Properties Fresh and 5-Star Worthy

15:00 – The Upgrade Clause: Property Improvement Plans That Scale Value

17:00 – The Cleanliness Factor: Deep Cleaning Every Quarter Pays Dividends

19:00 – Messaging Mistakes: Why Over-Communication Kills Guest Experience

21:00 – Final Recap: 7 Things Hosts Do That Secretly Cost Them Reviews

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

Ep 240 - New STR Data Revealed: What AirDNA Is Seeing (And What You Should Do Now) with Jamie Lane May 05, 2025

Show notes

THE STR GAME HAS CHANGED AND THE DATA PROVES IT.

AirDNA’s Chief Economist Jamie Lane joins the show to break down what’s actually happening behind the scenes in the short-term rental market...

...and why most hosts are missing the shift.

Inside this episode:

The real story behind occupancy, rates, and guest demand in 2024
Why “big box” managers are losing properties fast
The key numbers top investors are watching (and how to use them)
How AirDNA’s new tools are reshaping STR deal analysis
The warning signs for hosts scaling past 50 units and what breaks first
Why small, well-managed portfolios are quietly outperforming everyone

You’ll also hear how Jamie’s team is using AI and custom comps to bring never-before-seen clarity to STR investing...

...and what you can do to stay ahead.

Listen now to future-proof your portfolio before the data leaves you behind.

03:30 – Supply Shock: Why New STR Listings Are Surging Nationwide

07:00 – Booking Behavior: How Travelers Are Changing Their Habits

10:00 – Revenue Realities: The Decline in ADR and Occupancy Rates

13:30 – Market Saturation: Top Cities Facing Over-Supply Pressures

17:00 – Strategic Advantage: How to Win in Competitive Markets

21:00 – Data-Backed Decisions: Using AirDNA to Stay Ahead

24:00 – The Investor Shift: From Arbitrage to Ownership Models

27:00 – Resilience & Risk: Preparing for Softening Demand Cycles

30:00 – Long-Term Outlook: What Smart Operators Are Doing Next

Guest Bio:

Jamie Lane is Vice President of Research for AirDNA, a short-term rental data & analytics company. He is responsible for data analysis, thought leadership, and leveraging advanced analytical techniques to provide new insights into short-term rental supply, demand, and pricing trends. He has been published in academic and professional journals and regularly speaks at lodging industry forums.

Prior to AirDNA, Jamie spent 10 years as an economist at CBRE, leading research, forecasting and data intelligence teams to support client analysis. Mr. Lane is an active member of the National Association of Business Economists and the Atlanta Economics Club. Jamie holds a B.S. in Economics from the University of Georgia and an M.S. in Business Economics from Georgia State University.

Guest Link:

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

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

Our TOPPODCAST Picks

Follow Us

Stay Connected

Short Term Rental Secrets Podcast

Related Podcasts

Links

Stay Connected