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)

#353 - Should I Buy My First Sailboat?

Indie Founder

#353 - Should I Buy My First Sailboat?