How a $150k Insurance Check Built a STR Empire | Carole Anderson

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In this Client Success Spotlight episode, I talk with Carole Anderson—a former corporate accountant turned real estate investor—about how she built a thriving short-term rental portfolio after the sudden loss of her husband. Carole shares how she went from managing one Airbnb in her basement to running nine STRs, including owned properties, arbitrage units, and co-hosting arrangements. We also discuss the importance of clean books, building great systems, and how she’s turning her cost centers into profit centers by launching complementary businesses like cleaning and bookkeeping services. This is an inspiring story of resilience, resourcefulness, and long-term vision.

Timestamps:

00:00:00 – Carole’s first impression of Ryan’s boot camp

00:00:44 – Carole’s education and accounting background

00:01:54 – Leaving corporate America to pursue real estate full-time

00:02:35 – How accounting skills helped her succeed in STRs

00:04:50 – The story behind her very first Airbnb

00:06:14 – Why her target guest isn’t who you’d expect

00:08:28 – Carole’s current portfolio: 9 properties with diverse strategies

00:09:34 – Funding her first STRs with life insurance after a family tragedy

00:11:36 – How she scaled through smart investing and timing

00:13:31 – Selling a non-compliant STR and reinvesting profits

00:15:10 – Why she loves arbitrage (and how she pitches landlords)

00:16:56 – Why she’s focused on her local Utah market

00:18:38 – Turning her cleaning costs into a scalable business opportunity

00:20:31 – How she found Ryan through YouTube and joined the boot camp

00:23:39 – Why she’s switching from her local CPA to Ryan’s team

00:26:18 – “Are you the one changing your family tree?” Carole’s powerful answer

00:28:27 – Launching her direct booking site and plans to scale even further

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*None of this is meant to be specific investment advice, it's for entertainment purposes only.