I talk about my personal dilemma: should I buy a boat now or wait? I share my love for sailing, the costs and challenges of boat ownership, and my ideas to make it affordable—like renting it on Airbnb. I discuss chasing dreams versus saving or investing money, and ask if achieving goals is better than the journey itself. Finally, I mention trying to negotiate the boat price by offering my web skills. I’d love your feedback—message me on Twitter (@wbtiago).My Twitter: https://x.com/wbetiagoTimestamps by PodSqueezeIntroduction and Personal Dilemma (00:00:01)  Podcast Housekeeping & Audience Engagement (00:00:52)  The Caribbean Fisherman Story (00:01:56)  Reflection on Chasing Success (00:03:00)  The Gambler and the Devil Story (00:05:13)  Current Financial Situation (00:06:34)  Passion for Sailing and Background (00:07:36)  Debating the Investment (00:08:41)  Understanding the Value of the Chase (00:09:42)  Practical Challenges of Boat Ownership (00:10:51)  Marina Costs and Scarcity (00:12:02)  Boat Depreciation and Resale Value (00:13:15)  Offsetting Costs: Airbnb Rental (00:14:20)  Offsetting Costs: Tourism Experiences (00:15:23)  Offsetting Costs: Renting to Sailors (00:17:17)  Focusing on Airbnb as the Best Option (00:18:12)  Negotiating with the Boat Owner (00:19:20)  Next Steps and Request for Advice (00:20:16)  Episode Wrap-Up and Recommendation (00:21:21)

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#353 - Should I Buy My First Sailboat?

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