She Started With One Beach Condo, Now Manages 20+ Properties

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In this episode, I talk with Chelsea Cutrer—former tech executive turned short-term rental queen—about her incredible journey from W2 to full-time real estate entrepreneur. Chelsea shares how she leveraged her design eye, sales background, and business instincts to build a growing STR portfolio in the competitive 30A market. We dive into the systems she uses to manage her own properties and her 20+ management clients, her take on revenue strategy, and how she’s already changing her family tree.

Timestamps:

00:00:00 – Intro and Transitioning from W2 tech job to full-time STR investor

00:01:08 – Education, career at Dell, and early interest in real estate

00:04:14 – How Chelsea’s mom inspired her real estate journey

00:05:38 – Buying the first STR during COVID and the tax motivation behind it

00:08:40 – What makes her listings outperform in 30A

00:10:10 – The power of private beach access and listing clarity

00:14:45 – What her current STR portfolio looks like

00:16:26 – Markets she’s exploring next (like Cape San Blas)

00:19:04 – From co-hosting to full management and revenue strategy

00:20:21 – The biggest mistakes property managers make

00:22:36 – How she prices for the off-season and fills gaps

00:24:40 – Teaching her kids real estate and building generational wealth

00:26:40 – Growth plans, S Corp planning, and how she found Ryan

00:28:54 – Her top advice for anyone thinking about leaving their W2

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