December 02, 2025
#161 How One Woman Built a Multi-State Airbnb Business
Ever wondered if a passing joke could actually spark a life-changing real estate strategy? In this episode, we sit down with Sandy Lee and dive into how she built a multi-state Airbnb business—a journey that started with a simple joke about buying a ski condo for her son and unfolded into a thriving short-term rental portfolio across four states.
For Sandy Lee, building an Airbnb business in multiple states wasn’t about luck, shortcuts, or stumbling into the right property. It was about strategy, clarity, and a willingness to reinvent herself after a decades-long career in engineering. Her story proves that success in short-term rentals doesn’t require years of real estate experience—it requires intention and the right systems.
Ever curious about what it really takes to manage Airbnbs across different markets? Sandy pulls back the curtain and shows us how she’s using financial modeling, detailed market research, well-built systems, and teams she trusts from afar.
From Engineer to STR Investor
Sandy spent 30 years in oil and gas engineering before pivoting into real estate. She brought her analytical, detail-oriented mindset to the STR space, using financial modeling, cash flow analysis, and careful market research to identify properties with strong potential.
“I realized my engineering background gave me a unique advantage in evaluating properties,” Sandy says. “It wasn’t about luck—it was about strategy and understanding the numbers.”
Her approach is intentional: she chooses properties not only for cash flow but also for lifestyle alignment, ensuring each investment supports both her financial goals and personal freedom.
Systems and Teams That Make Remote Ownership Possible
With properties in four different states, Sandy quickly learned that systems and reliable teams are the backbone of scalable STR investing.
She implemented:
- Remote management strategies including property management software and local contractors
- Clear financial tracking to monitor profitability and ROI
- Automated guest communication to maintain a consistent experience
This combination of tools, processes, and people allows Sandy to scale without being tied to any one location, freeing her to enjoy life while her portfolio grows.
Wealth-Building Through Intentional STR Investments
Sandy’s portfolio isn’t just about accumulating properties—it’s about building long-term wealth with purpose. She focuses on metrics that matter: cash flow, appreciation potential, and risk-adjusted returns.
Her journey offers a blueprint for anyone who wants to:
- Turn a single property into a replicable investment model
- Use analytics and strategy to make informed decisions
- Build a business that generates freedom and meaningful income
“The first property was a fun experiment,” Sandy reflects. “But as I applied strategy and structure, it became a real wealth-building engine.”
Takeaway: It’s Never Too Late to Reinvent Yourself
Whether you’re decades into a career or just getting started, Sandy’s story proves that strategic investing paired with smart systems can transform your life. It’s about taking intentional action, leveraging your strengths, and creating opportunities where others see obstacles.
For hosts and investors seeking a portfolio that delivers both income and freedom, Sandy Lee’s journey is a masterclass in clarity, strategy, and mindset.
Tune in now to learn how a family joke turned into a wealth-building short-term rental empire.
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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