Short Term Rental Secrets Podcast

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.

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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:
Why tech stack decisions are emotional, not logical
How disconnected tools quietly create leadership stress
The difference between automating tasks vs removing hospitality
What luxury hotels get right about training and consistency
Why leaders must absorb pressure instead of passing it down
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:
Why your calendar tells the truth about your real priorities
The “perfect week” exercise that exposes misalignment fast
Why every new level requires letting go of your old identity
How fear, comfort, and ego silently slow your progress
The power of small, consistent actions over big intentions
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:
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