From Hurricane Loss to 70 Rentals: Scaling STR Business

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What happens when a hurricane wipes out one-third of your short-term rental portfolio in just two weeks, and forces you to rethink everything about how you operate, scale, and survive?

In this episode of Get Paid For Your Pad, Kaye Putnam (Head of Marketing at Freewyld and Freewyld Foundry) sits down with Joe Prillaman, co-founder of Host Help, to unpack how a natural disaster became the unexpected turning point that pushed him from managing his own properties to building a professional STR management company overseeing nearly 70 homes.

Joe shares the raw reality of losing properties to hurricanes and floods, carrying fixed mortgages and team costs, and realizing that managing for owners is a completely different business than managing your own portfolio. This conversation explores the operational stress, leadership decisions, and system-building required to rebuild stronger—without sacrificing guest experience, five-star reviews, or long-term vision.

Whether you manage 10 listings or are already scaling a full property management operation, this episode offers a clear look at what actually breaks as portfolios grow, why quality must be built upfront, and how crisis often accelerates the lessons most operators learn too late.

You’ll discover:

• How losing one-third of a portfolio forced a major STR business pivot

• Why managing owner properties is far harder than managing your own

• What changes operationally when you move from 30 to 70 rentals

• Why “cute, clean, comfortable” still drives five-star reviews at scale

• How guest experience systems prevent small issues from becoming disasters

• Why quality onboarding saves years of operational pain

• How pricing becomes the highest ROI activity once systems stabilize

• Why removing ego is essential as teams and portfolios grow

• How disasters expose weaknesses most operators overlook

• What it really takes to scale STR management sustainably

Joe and Kaye also explore how hurricanes and floods reshaped Host Help’s risk management approach, why disaster preparedness must be built into STR operations, how AI is reducing daily workload without replacing people, and why most operators underestimate the staffing and systems required to scale beyond survival mode.

💡 Topics Covered:

• STR portfolio loss and crisis-driven growth

• Scaling short-term rental management companies

• Guest experience systems and five-star reviews

• Onboarding processes and operational checklists

• Pricing strategy as a leverage point

• Leadership roles and team structure

• Disaster preparedness for coastal STR markets

• AI in guest communication and operations

• Seasonal profitability in beach destinations

🔗 Relevant Links:

Learn more about Freewyld Foundry → https://www.freewyldfoundry.com

Follow Kaye Putnam → https://www.linkedin.com/in/kayeputnam

Follow Freewyld Foundry → https://www.linkedin.com/company/freewyldfoundry

Keywords:

airbnb, short-term rentals, STR property management, scaling STRs, hurricane disaster, STR portfolio loss, vacation rentals, property management systems, guest experience, five-star reviews, STR operations, revenue management, pricing strategy, AI in hospitality, coastal rental markets, STR growth, Freewyld, Freewyld Foundry, Get Paid For Your Pad, Kaye Putnam, Joe Prillaman, Host Help, vacation rental management, scaling property management businesses

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