February 18, 2025

From Accidental Host to STR Mogul: How Sheila Dickinson Built Her Real Estate Empire

50 minutes

Curious about how to use a self-directed IRA to invest in real estate? This episode is a must-listen! I sat down with Sheila Dickinson, a former federal government employee who turned a chance encounter with short-term rentals into a thriving business across multiple states.

Sheila takes us through her incredible journey—from accidentally stepping into the vacation rental world to strategically using her self-directed IRA to grow her real estate portfolio. She shares the challenges she faced, the lessons she learned, and the strategies that helped her succeed.

Get insights into her unique approach to property management, her passion for design, and the importance of building a strong community. Whether you're an experienced investor or just starting out, Sheila’s story will equip you with the knowledge and motivation to scale your own short-term rental business.

Don't miss this insightful conversation—it just might change the way you think about real estate investing!

HIGHLIGHTS AND KEY POINTS:

[01:46] A short introduction about our guest Sheila Dickinson and how she got started in the world of short-term rentals

[06:25] Sheila’s growth path from two to nine short-term rentals using diverse financing strategies

[08:47] Sheila’s experience co-investing in real estate with her son and how it shaped his path into flipping properties

[12:29] Navigating real estate investing with Sheila’s husband and the challenges and rewards of working together as a couple

[15:48] Sheila’s insights on building a support network in the short-term rental community

[21:35] Sheila explains the self-directed IRA and the benefits and challenges of using it for real estate investments

[27:11] How Sheila educated herself on self-directed IRAs and real estate investing

[29:12] What are the biggest surprises Sheila encountered in growing her real estate portfolio

[34:30] How Sheila’s goals have changed over the years while growing her real estate portfolio

[39:42] Sheila’s favorite thing about having or being in short term-rental industry

[42:40] The lightning round

Golden Nuggets:

“If you don't have a supportive spouse at home, I think it is so incredibly important to surround yourself with people who are a support system, whether It's other women in the short term rental space, folks in your local communities, I think it's so important to have a support network.”

“There are so many wonderful benefits about having an online community. But when you're able to come together and sit next to each other, and sometimes hold each other's hand or hold up a glass of wine, there's just something so incredibly powerful about that.”

“My recommendation is find the stuff that you don't like to do and hire great people to do it, because they'll be lit up by that work if it's within their zone of genius, and it frees you up to do what you love too.”

“When I have something hard to do, if you have to swallow a frog, swallow it quickly, so just get it done.”

Let’s Connect!

Facebook: https://www.facebook.com/EscapesBySheila

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

Website: https://escapesbysheila.com/

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By Stacey St. John

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