The Tim Ferriss Show #815 · June 9, 2025 · 2h 39m

Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, and Avoiding The Optimizer's Curse

Chris Hutchins — the person who helps Ferriss burn 15M+ miles and points. Travel hacking, Costco gold arbitrage, $222 flights to Japan. But the real insight is the 'optimizer's curse': when the optimization takes more time than it saves.

Highlights

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The optimizer's curse

Spending more time optimizing than the optimization saves.

Claude ChatGPT Gemini

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Loyalty programs are worth more than the airlines themselves

Airline loyalty programs valued at $22-26 billion — more than the airline.

Claude ChatGPT Gemini

Misc

✧Helped Ferriss burn 15M+ miles and points

✧Flew to Japan for $222

✧Flipped Costco gold bars into five-star trips — gold pseudo-arbitrage at retail

✧Previously founded Grove (acquired by Wealthfront) and Milk (acquired by Google)

✧Was a Partner at Google Ventures