Ep 239 - How Ashley Freeman Built a 105-Unit STR Business After Hitting Rock Bottom

DIVORCED, BROKE… THEN SHE BUILT A 105-UNIT STR BUSINESS.

Ashley Freeman wasn’t supposed to be here.

Divorced, struggling to make ends meet as a tennis pro.

She took a chance on Airbnb with her farmhouse.

Now she manages over 105 units, leads a team of 25……

and lives a life most people only dream about.

In this powerful episode, Ashley reveals:

• How a side hustle became a 7-figure business
• The mindset shifts that changed everything
• Why systems + a strong team scaled her from 4 to 100+ properties
• How she created a 5-star guest experience that owners can’t stop raving about
• The identity shift required to step into true leadership

Success doesn’t happen overnight.

It happens when you refuse to quit.

Listen now and see how Ashley built an empire…

…one step, one belief, and one property at a time.

03:30 – From Rock Bottom to Rising Entrepreneur: Ashley’s Journey

07:00 – Faith, Grit, and Overcoming Self-Doubt in Business

10:00 – Rebuilding Self-Image: How Belief Rewires Success

13:30 – Tactical Scaling: Systems, Team Building, and Leadership Lessons

17:00 – Secrets to Sustainable Growth: Mindset, Service, and Strategy

20:30 – Life by Design: Building Freedom Through STR Success

24:00 – Living the Dream: Redneck Ranch, Soccer Travels, and Family First

Guest Bio:

Ashley Freeman is a 7-figure short-term rental expert who transformed her life through the power of short-term rentals. Starting with just one property, she scaled her business to 105 properties in under three years, growing from less than $50,000 in her first year to $2 million annually by year three, with the support and mentorship of STR Secrets and Conway Consulting. Passionate about serving others, Ashley is dedicated to helping people find the same freedom and life-changing opportunities that the short-term rental business gave her.

Guest Link:

https://www.instagram.com/velvet_ditch_villas

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