#353 - Should I Buy My First Sailboat?

#353 - Should I Buy My First Sailboat?

Author: Tiago Ferreira July 28, 2025 Duration: 22:24

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)


Tiago Ferreira is a full-time builder, an Indie Founder who operates without venture capital, turning ideas into revenue-generating startups entirely on his own terms. This podcast is the audio journal of that specific journey, focused on the craft of entrepreneurship and the tangible goal of hitting $100,000 in annual recurring revenue. You’ll hear Tiago’s own candid reflections-the wins, the setbacks, and the daily lessons learned while bootstrapping. The conversations extend beyond his own desk, featuring interviews with other entrepreneurs who understand the grind of building something from nothing. It’s a deep dive into the practical realities of independent creation, from product development and marketing to mindset and sustainable growth. Tuning into this podcast feels like getting real talk from a fellow maker who’s in the trenches, making it a valuable companion for anyone navigating the often solitary path of building a business with autonomy at its core. The focus remains squarely on actionable insights and shared experiences within the indie maker community.
Author: Language: English Episodes: 50

Indie Founder
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