Experiment, Adapt, Repeat: Turning Watersports into an Experience Brand Ft. Michael & Taylor Withrow - Episode #202
This episode, they guys sit down with Michael and Taylor Withrow, owners of Island Head in Hilton Head, South Carolina. They unpack what it really takes to build and sustain a diversified, multi location watersports and experience business. From early legal challenges that forced a rebrand, to expanding beyond parasailing into ferries, charters, and unexpected wins like a Hibachi cruise, the conversation is packed with real world operator lessons. Both guests share honest insights on failed ventures, experimentation, and resilience in a seasonal market. This episode offers practical takeaways on diversification, risk management, innovation, and how to think long term when running complex on water operations.
[SPONSORS] - This show is sponsored by Take My Boat Test and WaveRez.
Show Links:
Website: https://www.watersportpodcast.com
Facebook Page: https://www.facebook.com/awgpodcast
Facebook Group: https://www.facebook.com/groups/1155418904790489
Instagram: https://www.instagram.com/awg_podcast/
Owners
Michael and Taylor Withrow are the founders of Island Head, a company built from the ground up in the watersports industry. They started by renting boats and working a jet ski barge, truly at the bottom of the pecking order.
In 2012, they launched Island Head with just a single parasail boat and one jet ski used to pull a banana boat. What followed was an unconventional growth path shaped by the realities of entrepreneurship: adapting, pivoting, and thinking beyond the obvious.
Over time, Island Head evolved from a watersports operation into a full experience based company, focused on hospitality, lifestyle, and creating memorable moments. Today, Island Head Brands operates a fleet of over 40 boats, including 11 Coast Guard inspected vessels, across five marinas, and manages more than 30 short term rental properties, with no plans of slowing down.
