DiscoverIndie Founder#353 - Should I Buy My First Sailboat?
#353 - Should I Buy My First Sailboat?

#353 - Should I Buy My First Sailboat?

Update: 2025-07-28
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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 )

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#353 - Should I Buy My First Sailboat?

#353 - Should I Buy My First Sailboat?

Tiago Ferreira