#353 - Should I Buy My First Sailboat?
Description
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/wbetiago
Timestamps by PodSqueeze
Introduction 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 )








