Our Best And Worst Investments of 2025

TL;DR

The hosts (Sean, Sam, Steph) review their year across categories: best/worst financial and personal investments, personal L’s, frame‑breaking people, favorite guests, biggest changes, and memes. Key conclusions: Sam’s best investment was moving to NYC and buying a furnished apartment; Sean’s best was a one‑day stock shopping spree (Shopify, Tesla, Eli Lilly, Bitcoin, Coinbase, Google) returning ~3

Key insights

• The "misogi" concept from Jesse Itzler: pick one hard, year‑defining challenge so you remember each year by that event (e.g., learning piano, running an Ironman).
• "Frame‑breaking" people expand your sense of what’s possible – examples include Will Guidara (unreasonable hospitality), Kristen Berman (buying adjacent apartments to build community), and Fiona Oakes
• Money can be used as a tool to improve life (e.g., buying a compound for friends) or as a measuring stick – most people default to the latter.