Ep 279 - Why Conviction Beats Experience in Building a Real STR Business with Hailie Anderson
Mon Feb 02 2026
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/
More
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/