February 03, 2026
#170 Stop Building Islands: How to Start Scaling Your STR Business into an Empire
Ever felt like you’re building an empire on an island? You’re carrying the entire mental load of your business while wondering why there isn’t a roadmap for women like you? Scaling to the top of this industry requires more than just strategy; it requires the grit to go first and the heart to bring others with you. In this podcast episode, I sat down with the legendary Lisa Roads, who grew a UK property portfolio into a powerhouse managing over 175 luxury villas in Cyprus. We’re diving deep into why scaling your STR business means moving beyond the “just a host” mentality and leading with legacy.
Why Scaling Your STR Business Requires a Solid Foundation
Scaling is not just about adding more doors to your portfolio. If you add properties to a broken system, you aren’t growing—you are just scaling chaos. Lisa learned this the hard way when she scaled up to 220 properties before realizing that not every door is a “good” door. She made the bold CEO decision to scale back to 175 high-quality, aligned units to protect her profitability and her peace.
Before you take that next leap, you must master what Lisa calls the “Six Ps” of a successful operation: People, Positioning, Profitability, Financials, and Processes. If your foundations are shaky, the weight of growth will create cracks that eventually bring the whole house down. Boss up and get your “sausage machine” of bookings and operations working perfectly before you try to expand into new markets.
Creating Your Own Market with a Direct Booking Brand
When Lisa started in 2003, the major Online Travel Agencies (OTAs) we rely on today didn’t even exist. She had to create her own market from scratch. This forced her to build a robust direct booking brand through high-level collaboration and partnerships with travel agents. This wasn’t about paying massive commissions; it was about building trust and allowing partners to uplift prices for a win-win scenario.
In our sisterhood, we know that brand loyalty is worth more than any algorithm. By focusing on a high-touch, boutique experience, Lisa created such a strong connection that guests still send her Christmas cards years after she sold her business. When you focus on scaling your STR business, you must prioritize owning your guest data and your reputation over relying solely on a third-party platform.
Managing the Invisible Load of the Female Entrepreneur
We all wear an invisible backpack, Lady. We are scaling businesses while managing households, fixing dinner, and navigating the seasons of life. For Lisa, the mental load became almost unbearable while navigating the “sandwich generation” struggle—caring for aging parents with dementia while managing her own health during menopause.
You cannot operate on an empty cup. If you are running on fumes, you are no good to your business or your family. Scaling your STR business requires you to set non-negotiable boundaries. For me, that means tracking downtime hours as a key metric. For you, it might mean finally investing in a VA or a management team so you can step away without the world ending.
The Power of the STR Brain Trust
One of the most rewarding parts of this journey is seeing women gain the confidence to stop saying “I’m just an Airbnb host” and start acting like a CEO. Success in this industry is a lonely road if you try to walk it alone. You need a community where you can tap into a “brain trust” of women who will give you real, honest answers.
According to the Castell Project’s Women in Hospitality Leadership report, women hold only about 22% of senior management positions despite making up 70% of the workforce. This is why we lift each other up. True success is not just about the daring leaps we take for ourselves, but the space we carve out for other women to be heard and celebrated.
Your Next Steps Toward Empire Building
Scaling is a vocation, not just a job. It requires you to know your numbers, trust your gut, and ignore the naysayers who don’t understand your purpose. If you are ready to move beyond the grind and start leading with legacy, remember that you are stronger than you think you are.
Boss up, Lady! Go out there and build the empire you were meant to lead.
Click here now to listen to the full podcast.
HIGHLIGHTS AND KEY POINTS:
[01:01] A short introduction about our guests Lisa Roads, and shares her journey from long-term investor to industry leader while explaining her mission to elevate and support women in the short-term rental space
[05:31] Lisa Rhodes and I reflect on the power of women-centered communities to build confidence, visibility, and leadership in short-term rental businesses
[11:38] Lisa shares the realities of scaling a property management business to 175 high-performing properties by prioritizing alignment, systems, and long-term profitability
[14:22] Lisa emphasizes the importance of intentional, systems-driven growth over chasing door count and scaling chaos in large property management portfolios
[16:29] How intentionally defining the ideal guest, designing for that audience, and building strategic partnerships allowed Lisa to create demand in an undeveloped short-term rental market
[18:11] Lisa on creating high-trust travel agent partnerships and the operational systems that made them scalable
[20:51] Lisa explains how she built custom systems to manage bookings, property operations, and service delivery in a market without established short-term rental technology
[22:31] How building a support network was essential to managing the invisible mental load of running a business and caring for family
[25:50] Lisa emphasizes the importance of setting boundaries, protecting mental and physical health, and intentionally scheduling downtime to prevent burnout as an entrepreneur
[29:19] Lisa reflects on growing up in an entrepreneurial, nomadic family, and emphasizes the importance of self-belief and having a solid business plan when facing naysayers
[33:28] Lisa reflects on starting over in short-term rentals, emphasizing foundational strategy, guest experience, and building a direct booking brand
[35:57] The lightning round
Golden Nuggets:
- “It’s incredibly powerful to have a community around you where you can hack into that knowledge.”
- “It’s better to have 175 really good properties and really good aligned relationship landlords than to have 220 just not doing very well.”
- “To try and scale on something that’s not solid is going to be painful. You’re just going to have big holes.”
- “Without a support network, it can be virtually impossible to pull through certain situations.”
- “Don’t let those naysayers derail you from something you’re incredibly passionate and committed to doing.”
- “When you focus on the right things, the money will follow.”
- “Keep on top of your finances. Know your numbers, don’t operate a business and be naive about your numbers.”
Let’s Connect!
LinkedIn: https://www.linkedin.com/in/lisaroads/
Website: https://theholidaypropertycoach.wordpress.com/
Facebook: https://www.facebook.com/profile.php?id=100082839816462
Did you enjoy the episode? Don’t forget to Subscribe, Rate, Review, Like, and Share!
