FEBRUARY 18, 2025
#120: How to Invest in Short-Term Rentals: Sheila Dickinson’s Journey from Accidental Host to STR Mogul
Turning a Chance Encounter into a Thriving STR Business
Have you ever wondered how to invest in short-term rentals and turn a single decision into a thriving business? Sheila Dickinson’s journey into the world of short-term rentals (STRs) is nothing short of inspiring. A former federal government employee, Sheila stumbled into the vacation rental industry by chance—but she didn’t stop there. Using strategic investing and leveraging a self-directed IRA, she built a flourishing real estate empire across multiple states.
In this episode, Sheila shares her incredible transformation from an accidental host to a real estate mogul. She opens up about the challenges she faced, the lessons she learned, and the strategies she used to scale her STR business. Whether you’re a seasoned investor or a beginner, her story is packed with actionable insights that can help you grow your portfolio.
How Sheila Built Her STR Empire
Sheila’s journey started with a single rental, but her keen eye for investment opportunities helped her grow a multi-property portfolio. By leveraging various financing strategies, she expanded efficiently while learning the intricacies of real estate. She embraced co-investing with family, bringing her son into the business, which provided both financial and experiential benefits. Managing properties with her husband brought its own set of challenges and rewards, reinforcing the importance of partnership in real estate.
A key factor in Sheila’s success was her ability to build a strong support network. She emphasizes the importance of connecting with like-minded individuals, both online and in person, to navigate the complexities of the STR industry. Additionally, she strategically utilized a self-directed IRA to fund her real estate investments, a powerful yet often overlooked tool that allowed her to scale her business.
Key Takeaways
[00:00] A short introduction about our guest Sheila Dickinson and how she got started in the world of short-term rentals
[04:41] Sheila’s growth path from two to nine short-term rentals using diverse financing strategies
[07:03] Sheila’s experience co-investing in real estate with her son and how it shaped his path into flipping properties
[10:45] Navigating real estate investing with Sheila’s husband and the challenges and rewards of working together as a couple
[14:05] Sheila’s insights on building a support network in the short-term rental community
[19:55] Sheila explains the self-directed IRA and the benefits and challenges of using it for real estate investments
[25:30] How Sheila educated herself on self-directed IRAs and real estate investing
[27:31] What are the biggest surprises Sheila encountered in growing her real estate portfolio
[32:49] How Sheila’s goals have changed over the years while growing her real estate portfolio
[38:08] Sheila’s favorite thing about having or being in short term-rental industry
[41:05] The lightning round
Golden Nuggets
- “If you don’t have a supportive spouse at home, it is so incredibly important to surround yourself with a strong support system.”
- “There are so many wonderful benefits to having an online community, but meeting in person adds a whole new level of support and motivation.”
- “My recommendation: find the stuff you don’t like to do and hire great people to do it.”
- “If you have something hard to do, swallow the frog quickly just get it done.”
Ready to Scale Your STR Business?
Sheila’s story is proof that with the right strategy, knowledge, and support, anyone can turn short-term rentals into a thriving business. Whether you’re just starting out or looking to scale, her insights will give you the tools and inspiration you need.
Want to learn more? Listen to the full episode and take the first step toward growing your own real estate empire!
Let’s Connect!
Facebook: Escapes by Sheila
Instagram: @escapes_by_sheila
Website: Escapes by Sheila
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