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From Accidental Investor to Mentor

How Entrepreneur Stacey St. John Helps Women Build Confidence, Freedom + Stability through Real Estate

Stacey St. John didn’t set out to build a real estate business. 

When her son planned to leave Cincinnati to attend a Florida university that did not offer student housing, Stacey and her husband purchased a small condo in Orlando rather than pay rent. Weeks after closing, their son changed his plans and enrolled online instead.

“We were suddenly owners of a vacant property,” Stacey shares. “So we rented it out—and realized we were actually making money.”

That unexpected start sparked a deeper interest in real estate investing. 

At the time, Stacey was serving on the leadership team of a global consulting firm, overseeing sales and account management. Real estate offered something different: the opportunity to build long-term wealth while creating flexibility for her family.

Initially, she and her husband invested in long-term rentals in Ohio. But in 2020, when eviction moratoriums made many landlords nervous, they pivoted.

“With short-term rentals, guests have to pay before they walk through the door,” Stacey says. “That model made more sense for us at that moment.”

In September 2020, they purchased two condominiums in Myrtle Beach, renovated them and entered the short-term rental market. Today, Stacey operates multiple properties, holds a property manager license in South Carolina and runs a full-service management company there. Some properties operate strictly as vacation rentals, while others use a hybrid model, offering both short-term and mid-term furnished stays.

As her business grew, so did questions from others wanting to learn. 

In March 2021, Stacey launched a Facebook group, Female Short-Term Rental Investors, focusing on women investing in short-term rentals. Before long, she had a community of thousands learning to invest with confidence.

Today, the group includes about 66,000 members worldwide. Stacey also hosts the STR Sisterhood podcast, runs a membership community called STR Sisterhood and offers mentoring and mastermind programs.

At its core, her mission is to create a supportive space where women can define what they want, build a plan and grow businesses that create confidence, freedom and long-term stability.

“As women, we often carry what I consider an invisible load,” Stacey notes. “We’re building businesses while working a full-time job and acting as mom, chauffeur to our kids and homemaker.”

For those interested in rental investing but feeling intimidated, Stacey says education is the first step. She encourages aspiring investors to learn how to analyze a deal properly before purchasing.

“Most of your money in real estate,” she explains, “no matter whether you're investing in long-term, mid-term or short-term rentals, is made on the front end when you buy.”

Learning deal analysis, negotiation strategies and how to acquire properties in a strategic manner is paramount. 

She also recommends connecting with local organizations, such as the Real Estate Investors Association of Greater Cincinnati and COREE (Community of Real Estate Entrepreneurs), to build relationships and learn from experienced investors.

One of the biggest misconceptions, she says, is that rental properties mean constant emergencies and stress.

“Do things come up? Absolutely,” Stacey says. “But with clear processes and the right team in place, it’s manageable. Ninety-nine percent of the time, we have fabulous guests.”

Looking back, she says learning to trust her gut—especially when hiring contractors or team members—has been one of her most important lessons.

Despite shifting market headlines, Stacey remains optimistic about the future of real estate.

“There are always opportunities,” she says. “Real estate remains one of the most strategic ways to build wealth for your family.”

To learn more about Stacey’s work, including her book “LIVE BIG,” or to connect with her growing community of women investors, visit StaceyStJohn.com.

At its core, Stacey St. John's mission is to create a supportive space where women can define what they want, build a plan and grow businesses that create confidence, freedom and long-term stability.