Are you ready to transform your short-term rental business from a chaotic side hustle into a thriving, systemized empire?

In this episode, I sit down with Kit Leggett, a fearless entrepreneur who went from jobless during COVID to managing 35+ properties —and building a business culture so powerful, her team calls it their favorite place to work.

Kit’s journey is anything but ordinary. After losing her job, she took a leap of faith, and started investing in real estate. But what truly sets her apart isn’t just the number of properties—it’s the heart behind her business. She’s created a supportive, women-powered team where flexibility is real, kids are welcome at work, and team bonding includes zip-lining adventures.

We dive into how Kit scaled her business, the software that keeps things running smoothly, and the mindset shifts that helped her overcome the fear of growing too fast. Her story is a powerful mix of resilience, innovation, and redefining leadership in an industry that often overlooks the human side of success.

If you're dreaming of your first rental or ready to scale with soul, this episode will inspire you to build a business that thrives—from the inside out!

HIGHLIGHTS AND KEY POINTS:

[01:04] A short introduction about our guest Kit Leggett and what made her decide to start in the world of short-term rentals

[05:15] Kit shares what sparked her first STR listing during COVID, jumpstarting her journey in a booming market

[07:04] Kit recounts the emotional toll of doing everything herself early on, leading to a breakdown that pushed her to finally ask for help

[11:48] How hiring a local, all-women team transformed Kit’s business and became a mission-driven extension of her values

[13:59] Kit shares her client reactions and the day-to-day logistics of working with kids 

[16:33] What inspired Kim to create a work culture where kids are welcome

[19:09] How Kit’s team-first mindset and hands-on leadership organically created a loyal, supportive culture among her all-women staff

[24:25] Kit describes how she plans team activities organically and affordably, focusing on connection rather than formal budgets

[28:31] Kit shares how a casual coffee chat led to acquiring 13 hosting contracts through an informal but strategic business offer

[31:44] How Kit calculated a fair purchase price for hosting contracts using a practical, grounded approach

[34:15] Kit reveals how she financed her contract acquisition that did not require upfront cash

[36:01] Kit shares the single biggest factor enabling her to manage over 35 properties

[38:33] Kit’s perception of failure and her response to setbacks

[40:04] Kit reveals a game-changer software for automating operations and managing cleanings at scale

[42:37] How Kit structures scheduling and autonomy for her cleaning team

[44:44] Kit shares about her plan to expand beyond her local market

[47:11] The lightning round 

Golden Nuggets:

“When we find good team members, they're like gold to our businesses, and we want to do everything we can to keep them.”

“I just love supporting women, and we're a tight knit group, and we really rely on each other, and help each other.”

“Any kind of culture starts at the top, and works its way down.”

“When your team knows that you will bend over backwards to help them, they will do the same for you.”

“It's so important to test different things on the journey of continuous improvement. But give yourself grace when it doesn't work out and you have to pivot, that's okay.”

“The cleaners are the backbone of the business. And if you don't have a good team or good systems in place with good software, then you're going to be scrambling.”

“Surround yourself with people that do encourage you and do help you.”

Let’s Connect!

Website: https://stayinthevalley.com

Instagram: https://www.instagram.com/stayinthevalley/

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