How can you turn your dreams into a profitable real estate strategy that builds both wealth and freedom?

In this episode, I sit down with Sandy Lee, who pivoted from a 30-year career in oil and gas engineering to become a savvy short-term rental investor with properties across four different states. Sandy’s story is about reimagining what’s possible when you combine strategic thinking, personal passion, and a relentless drive to learn.

What started as a family joke about buying a ski condo her son dreamed of turned into a thriving investment portfolio that now generates meaningful retirement income. Sandy’s approach is rooted in intentional, long-term wealth building—where every property reflects both financial foresight and lifestyle design.

We dive into how Sandy leveraged her engineering mindset and financial modeling skills to build a short-term rental business that delivers more than just cash flow. From managing remote teams to identifying the financial metrics that truly matter, she shares the systems and mindset shifts behind her success.

This episode is a powerful reminder that it’s never too late to reinvent your career or your financial future. Sandy’s journey proves that with clarity, structure, and purpose, your investments can become more than assets—they can become the foundation for the life you’ve always envisioned.

HIGHLIGHTS AND KEY POINTS:

[00:50] A short introduction about our guest Sandy Lee, and how she got into the short-term rental industry

[05:10] Sandy shares how she went from doubting property ownership to building a multi-state portfolio that fuels her retirement 

[08:04] How aligning Sandy’s investments with her personal mission brings both joy and purpose to her real estate journey 

[10:44] Sandy talks about how continuous learning shaped her mindset shift toward early retirement and business reinvention 

[14:37] How leadership and appreciation elevate Sandy’s short-term rental business

[18:12] The importance of building genuine, caring relationships with the cleaning team and how Sandy found them in four different locations

[20:35] Sandy shares the challenges and lessons of managing teams across multiple short-term rental locations

[24:06] Sandy talks about the realities and rewards of managing short-term rentals from afar 

[26:40] The key financial metrics that Sandy uses to evaluate short-term rental investments 

[28:20] Sandy discusses the importance of tracking data-driven performance metrics after purchase to guide strategic decisions 

[32:08] Sandy discusses the importance of moving away from “ego pricing,” and trusting experts to strengthen business performance 

[34:42] Sandy shares her enthusiasm for bringing fresh energy into the short-term rental, and emphasizes the importance of thinking beyond the “get rich quick” mentality 

[35:38] The lightning round 

Golden Nuggets:

• “It's really important to figure out who you are, what you want from life, put that together and then make it happen.”
• “Don't wait for an opportunity, create it.”
• “You've got to keep learning, or you're paced out.”
• “People are your business, no matter how tiny your business is.”
• “It's okay to not know all the things. You learn as you go along, and you educate yourself every day.”

Let’s Connect:

Website: https://www.strjumpstart.com/

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

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