SEPTEMBER 16, 2025
#150 Scaling Short-Term Rentals: How Chelsea Cutrer Grew to 25 Properties in Just One Year
What would it take for you to leave behind a secure, six-figure tech career and bet on yourself instead?
For Chelsea Cutrer, the decision came after a management company mishandled her property with hidden charges and ignored damages. That frustration sparked a bold move: take control of her own rentals.
One year later, Chelsea was managing 25 properties and running a thriving short-term rental business. Her story proves that scaling short-term rentals is possible when you pair systems with vision—and the courage to walk away from what no longer serves you.
Why Systems Are the Secret to Scaling Short-Term Rentals
Chelsea’s background in tech gave her a huge advantage. She leaned into tools like:
- OwnerRez for streamlined management
- PriceLabs for dynamic pricing
- Virtual assistants to take tasks off her plate
The result? She could grow quickly without sacrificing quality.
If you’re serious about scaling short-term rentals, Chelsea’s story shows that systems aren’t optional—they’re the foundation.
From Two Properties to 25—Fast
Chelsea didn’t set out to build a business empire. At first, managing her own properties was about survival. But her results spoke for themselves, and soon other owners came knocking.
Her growth wasn’t just about saying “yes” to every opportunity—it was about saying “yes” to the right ones. Chelsea only takes on properties and owners that align with her vision and standards. That intentionality has kept her business strong, even through rapid expansion.
Want more strategies like Chelsea’s? Check out this guide to scaling your STR business.
Building a Business That Reflects Your Values
For Chelsea, this journey isn’t just about income—it’s about impact.
After losing her father to cancer, she realized she wanted work that felt exciting and meaningful, not just financially rewarding. That clarity has shaped how she chooses clients, manages properties, and leads her business.
Scaling short-term rentals isn’t just about growth—it’s about growth with purpose.
Wrap-Up
Chelsea’s story is proof that extraordinary things happen when you combine courage, systems, and strategy.
Whether you’re managing two rentals or dreaming of 25, her blueprint shows that scaling short-term rentals is less about hustle and more about being intentional—with your tech, your team, and your values.
So, are you ready to design a business that excites you as much as it sustains you?
HIGHLIGHTS AND KEY POINTS:
[01:13] A short introduction about our guest Chelsea Cutrer and how she got into short-term rentals
[03:30] Chelsea explains how lack of transparency and repeated issues with her property manager pushed her to take over and self-manage her rentals
[07:49] How Chelsea’s tech background and sales experience made the transition to self-managing her rental portfolio smooth and manageable
[09:48] Chelsea shares how quickly expanding from two to four properties convinced her to pursue short-term rentals full time
[10:49] Chelsea explains how leaving her tech job and helping others with their setups naturally grew into a co-hosting business that evolved into full-time property management
[12:22] Chelsea shares how mentoring others on tech and self-management grew into co-hosting, which later transitioned into full-time property management
[14:45] How shifting from coaching to full-service management led Chelsea to refine her offerings and streamline her business model
[16:18] Chelsea talks about her owner acquisition process and how her established business attracts more leads than she can handle, allowing her to be selective with owners based on fit, quality, and revenue goals
[18:07] How Chelsea evaluates potential properties for revenue, condition, and fit, while being honest with owners about whether she can take them on
[19:38] How Chelsea vets owners to gauge their openness to upgrades and alignment with delivering a great guest experience
[21:12] Chelsea shares how she’s growing her team with tech tools, a VA, and a real estate license while evaluating the best path for future expansion
[22:29] Chelsea reflects on how losing her father shifted her perspective from chasing money to pursuing passion and fulfillment in real estate and property management
[25:40] Chelsea explains how relocating from Texas to Florida was driven by passion, growth, and the ability to stay hands-on while leveraging her team
[27:27] Chelsea outlines the systems, contracts, and SOPs she built to support rapid growth and reduce liability
[29:41] Chelsea shares the tasks her VA handles and how delegation has helped her operate at a CEO level
[33:58] What are the biggest challenges that Chelsea has experienced as she has grown her portfolio quickly
[34:53] How Chelsea handled owners who resisted making updates and the difference it made when one owner listened and another didn’t
[39:46] Chelsea’s words of wisdom to those who want to grow their properties
[40:41] The lightning round
Golden Nuggets:
- “When you get the positioning right, with the decor, the marketing and the operations, it is a fabulous equation for performing above the market.”
- “Pushing through your comfort zone is so important. However, it’s so important when it’s something that lights you up and brings you joy. If it doesn’t bring you joy, don’t do it.”
- “Life is way too short to not be doing stuff that we love.”
- “Shifting from a doer to a leader is one of the most impactful gifts you can give yourself if you’re wanting to grow your portfolio.”
- “Add value wherever you can. If it’s a local market or on Facebook groups, be willing to help people, and don’t expect anything in return.”
- “Believe in yourself and put in the work.”
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