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

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

NEW AIRBNB POLICY JUST DROPPED...AND IT COULD KILL YOUR LISTING.

If you collect emails, drop a guidebook link, or offer guests early check-in via Venmo…

You might be in violation of Airbnb’s new policy.

In this episode, Mike Reilly breaks down exactly what Airbnb’s new off-platform & fee transparency rules mean for STR hosts.

And how to stay compliant without losing control of your business.

You’ll learn:

• The exact actions Airbnb will now penalize (even by AI detection)
• Why asking for an email could get you flagged
• How to safely use guidebooks, QR codes, and text marketing
• The only way to charge guests for add-ons (without breaking policy)
• The smart way to collect damage waivers and manage taxes without risk

If 80% of your bookings come from Airbnb, you can’t afford to get this wrong.

02:30 – Dangerous Moves: Why Secret Messaging Will Get You Flagged

05:00 – Booking Extensions & Repeat Guests: What’s Now Off-Limits

07:30 – Is Direct Booking Worth It? Margins vs Platform Protection

10:00 – Hostfully Links, Guidebooks & Legal Loopholes Explained

13:00 – Mandatory Disclosures: HOA Rules, Emails & County Compliance

15:00 – Fee Transparency: Avoiding Suspensions With Clean Listings

18:00 – Payment Violations: Why Airbnb Bans Zelle, Venmo & Side Deals

21:00 – Damage Waivers Over Deposits: How to Protect and Profit

24:00 – Airbnb AI Enforcement: Messaging Triggers and Flagging Risks

27:00 – Contact Info Restrictions: What You Can and Can’t Ask Guests

30:00 – SMS Tactics: Getting Verbal Consent and Staying Compliant

33:00 – Future-Proofing: Will Airbnb Eliminate Direct Contact?

36:00 – Review Removal Struggles: Why AI Appeals Are Failing Hosts

39:00 – Case Study: Retaliatory Reviews & the Fight for Fairness

42:00 – Platform Fatigue: Why Community Knowledge is Your Best Weapon

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com

HE BUILT 50 STR UNITS AND STILL WORKS A 9–5.

Ron Curtis didn’t quit his job.

He just built a business so efficient that he didn’t have to.

In this episode, Ron breaks down how he:

• Turned a $3,700 house hack into a 50-property portfolio
• Cleared over $10K in credit card debt and now manages $300K in available credit
• Uses his 9–5 income to fuel real estate moves without burnout
• Built systems, VAs, and SOPs to scale without stress
• Teaches financial literacy by living it, not just posting about it

You’ll also learn:

• Why relationships > money in cohosting
• The mindset shift that tripled his capacity
• And how he helped one client buy a $1M building, just from Airbnb cash flow

This episode is proof you don’t need to quit to win.

04:30 – Market Momentum: Flips, Deal Flow, and Fear-Based Opportunity

09:00 – Financial Literacy First: Foundational Principles for Entrepreneurs

13:30 – Zero to Fifty Listings: Scaling with Systems and Strategic Partnerships

18:00 – Designing Teams for Freedom: SOPs, VAs, and the Org Chart Blueprint

22:30 – The Mindset Shift: Working On the Business, Not In It

27:00 – Simplify to Scale: Letting Go of the Noise and Focusing on ROI

31:30 – Buying Back Time: Vertical Integration and Efficiency Hacks

36:00 – Real Client Wins: How STR Cashflow Changed Lives and Bought Freedom

41:00 – House Hacking & Books That Sparked a Million-Dollar Portfolio

Guest Bio:

Ron Curtis is a native Washingtonian and the founder of a short-term and mid-term rental management business based in the Washington, DC area. Ron's journey into short-term rentals started with house hacking—he leveraged first-time homebuyer programs to purchase his first home, a turnkey $423,000 property, for just $3,700 out of pocket. He converted his basement into a studio efficiency and listed it on Airbnb. As Ron traveled, he realized his basement was consistently booked and covering his mortgage. That’s when he fell in love with the concept of Paycations—earning passive income while exploring the world. He built an automated, scalable business model that allows him to manage rentals from anywhere with just WiFi and a reliable cleaning team. Over the last 3.5 years, he has organically grown from managing one property to 50—all while working a full-time 9–5 government job in DC. Ron loves to share his insights on scaling a short-term rental business, automation strategies, and how others can achieve financial freedom through short-term rentals.

Guest Link:

www.instagram.com/wavy_stay

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com