EPISODE 599: A short-term rental can look like a home run on a spreadsheet and still fail in real life. In today's market, building your strategy around best-case assumptions is one of the fastest ways to lose money.
So what does it actually take to know if a deal is worth buying?
In this episode ofThe Real Estate InvestHER Podcast, Liz sits down with Sandy Lee, a former corporate engineer who spent 30 years in engineering and construction and led the private equity arm of her firm. At 52, Sandy bought her first short-term rental, a four-bedroom ski condo in Steamboat, Colorado, for $1.3 million. That first property now cash flows around $5,000 a month. She went on to build a portfolio of short-term rentals across four states and retired two years later.
Sandy's approach to evaluating deals comes directly from her private equity background: instead of analyzing a snapshot in time, she builds a financial model that looks out 10 to 15 years. She factors in cash flow, appreciation, and mortgage paydown to calculate a true annualized return she can compare directly to stock market performance. Her returns range from the low teens to the mid-30s percent, on an annualized basis.
But the numbers are only part of the story. Sandy looks for what she calls the "special sauce," something specific happening in a market over the next few years that will push appreciation and demand in the right direction. With Steamboat, it was Aspen's acquisition of the resort, plans for a new gondola, and tightening regulations that reduced supply. She bought when the deal was only breaking even, knowing what was coming.
She also breaks down the operational side: the tech stack that cost her $125 a month and tripled her revenue, how she approaches regulations in every new market, and why she makes sure every property she buys would still cover its mortgage as a long-term rental, no matter what.
In this episode, you'll learn:
➡️ Why the numbers alone will not tell you if a deal is worth buying
➡️ How to spot the market "special sauce" that drives long-term growth
➡️ The private equity financial model Sandy uses to evaluate every deal
➡️ Why annualized return is the number that actually matters
➡️ How to think in 10 to 15-year windows instead of snapshots
➡️ The $125/month tech stack that tripled Sandy's revenue
➡️ How to research STR regulations before you commit to a market
If you are evaluating your first short-term rental or looking to grow an existing portfolio, this episode will change how you look at every deal.
Connect with Sandy:
Website
Instagram
Resources Mentioned In This Episode:
STR Jumpstart Tech Stack Guide Sandy's free graphic breaking down the exact tech stack she uses to run her short-term rental portfolio, including required tools and optional add-ons. Available at strjumpstart.com or @strjumpstart on Instagram.
PriceLabs Dynamic pricing software for short-term rentals that automatically adjusts your nightly rates based on market demand.
Resources to Support Your Next Step: Ready to go beyond the episode and take action to build wealth, achieve financial freedom and live the life you want?
InvestHER Assessment: Take this 5-minute quiz to determine where you are in your investment journey and receive a custom roadmap with practical steps you can start taking today.
STRIVE Mentorship Program: Stop growing your portfolio alone. Start building wealth with the right community behind you. STRIVE is a strategic framework that helps women real estate investors build wealth with more clarity, structure, and support.
Strategic Business Audit: You've built a real estate portfolio. Now it's time to build a business that supports the life you want. Gain clarity across your entire business, identify what's limiting your next stage of growth, and know exactly where to focus next.
InvestHER Fund: Investing in Women-Led Real Estate Projects. The InvestHER Fund is being built to allocate capital across multiple vetted real estate projects led by operators from the InvestHER community. The goal is to support experienced women operators with strong track records who have reached a capital growth barrier, while also fulfilling the needs of passive investors looking to diversify their portfolios through real estate investments that generate recurring income opportunities.
See you in the arena!
Liz + Andresa
Produced by: Social Chameleon
