Are you ready to discover how one woman walked away from a six-figure tech career to build a 25-property short-term rental empire in just one year?

In this episode, I sit down with Chelsea Cutrer, whose story is as bold as it is inspiring. Chelsea started like many hosts—frustrated with a management company that was nickel-and-diming her while neglecting her property. After uncovering mysterious charges and damage to her property that had been ignored for months, she made the gutsy decision to take control of her rentals herself.

Using her tech background and determination, Chelsea streamlined operations with tools like OwnerRez and PriceLabs—all while still working her full-time job. Her success was immediate, and soon other property owners were asking her to manage their rentals. What began as self-preservation quickly grew into a thriving business.

Chelsea opens up about scaling from managing two properties to 25, the challenges of rapid growth, and the lessons she learned about delegating to a virtual assistant. She also shares why she only takes on properties and owners that align with her vision, maintaining high standards across her portfolio.

Losing her father to cancer shifted her perspective, inspiring her to pursue work that truly excites her rather than staying in a high-paying but unfulfilling career. Chelsea’s journey is proof that pairing systems with passion and courage can lead to extraordinary results. Her insights on owner relationships, property selection, and building a values-driven business are packed with actionable strategies for anyone looking to grow in the short-term rental space.

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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