97: He Sold Everything and Moved to Costa Rica with Tony O'Neill
About this episode
The road to someday leads to a town called Never. That warning moved Tony from Indianapolis to a surf town in Costa Rica.
Tony O'Neill, founder of Highline Outdoor Group, runs executive search for the outdoor and sporting goods industry and once built Yeti's leadership team during its biggest growth run. He tells Keith Tyner and Doug Shrieve why he and his wife Marla were not trying to escape Indianapolis, and what finally made leaving practical.
This episode covers:
• Why paying off a mortgage created the capital for land abroad
• What selling a house by owner looks like with one showing window
• How location independence and time zones shaped the business model
• When a winter rental became a land purchase and an architect
• Whether a lifetime of belongings deserves one shipping container
Tony's one piece of guidance for anyone circling a move this big: do it immediately, don't wait.
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