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An In-Depth Discussion About How & Why I Left Everything for a Life at Sea

This is my wide-ranging interview (with timestamps!) w/ Caterina from Freedom Focus

Dear Readers,

I hope you enjoy my first Substack Live interview, which I did with the fantastic

from Freedom Focus. We got super deep into what motivated my big decision to give up my career for a years-long global sailing adventure, as well as how I’m navigating risk, uncertainty, and finances.

We also explored more universal topics, including the minuses AND plusses of “settling down,” and how to work toward impossible-sounding goals with finite bandwidth. I hope you get something out of this wide-ranging discussion.

Timestamps to help you navigate the conversation:

0:00 — What I’m doing with Radical Paths

2:35 — The origin story of my crazy idea to buy a sailboat & sail indefinitely

9:25 — The 1-year journey preparing our sailboat

11:19 — How my core principles helped me make this choice

18:45 — Navigating uncertainty & risk in this next chapter

27:10 — Preparing financially

31:55 — How we’re thinking about sustainability at sea

36:50 — Where we’re heading after we set sail

40:12 — Caterina’s journey and goals with Freedom Focus and life

44:25 — The minuses AND plusses of “settling down”

47:35 — Prioritizing where we spend our finite energy

51:06 — How living on a sailboat will allow me to build something bigger

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Also, thank you

, , , , , , and many others for tuning in during the live session.

Fair winds,

—Cory Vinny


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