Longtail Re's Strategy and Waiting Portfolio Treasure

"Today's the day."

~ Mel Fisher

Why does a reinsurance company's annual letter get me this fired up? Ross Stevens weaves together treasure hunting, Bayesian statistics, and the raw reality of Bitcoin as a human rights tool - culminating in a voice message from Nobel Prize winner Maria Karina Machado that moved him to tears. In my rant, I unpack why optimism isn't woo-woo, it's basic logic - and why waiting for certainty before believing in your own success is a guaranteed path to failure.

Check out the original article: Stone Ridge 2025 Investor Letter (Link: https://www.nydig.com/research/stone-ridge-2025-investor-letter)

References from the episode

• The Adaptability Quotient by Alec Litowitz - The forthcoming field guide for success mentioned in the letter.
• Wired for Story and Story Genius by Lisa Cron - My favorite books on what storytelling actually is. (Hint: it's not the plot!) (Link: http://wiredforstory.com/books)
• Fascinate: How to Make your Brand Impossible to Resist by Sally Hogshead - Fantastic on branding and narrative. (Link: https://a.co/d/5H1FJUy)
• Save the Cat by Blake Snyder - Useful for story pacing, but to be paired with Kill the Dog for balance.
  (Link: https://a.co/d/a1rp6Lc)
• Longitude by Dava Sobel (Link: https://en.wikipedia.org/wiki/Longitude_(book))
• The Human Rights Foundation (Link: https://hrf.org/)
• HRF Weekly Financial Freedom Reports (Link: https://hrf.org/newsletters/)

Host Links

• ⁠Guy on Nostr ⁠(Link: http://tinyurl.com/2xc96ney)
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• Guy on TikTok (Link: https://www.tiktok.com/@theguyswann)
• Guy on YouTube (Link: https://www.youtube.com/@theguyswann)
• ⁠Bitcoin Audible on X⁠ (Link: https://twitter.com/BitcoinAudible)
• The Guy Swann Network Broadcast Room on Keet (Link: https://tinyurl.com/3na6v839)

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• HRF: The Human Rights Foundation is a nonpartisan, nonprofit organization that promotes and protects human rights globally, with a focus on closed societies. Subscribe to HRF's Financial Freedom Newsletter today. (Link: https://mailchi.mp/hrf.org/financial-freedom-newsletter)
• OFF: The Oslo Freedom Forum is a global human rights event by the Human Rights Foundation (HRF), uniting voices from activism, journalism, tech, and beyond. Through powerful stories and collaboration, OFF advances freedom and human potential worldwide. Join us next June. (Link: https://oslofreedomforum.com/)
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