The Tim Ferriss Show

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

1464 snips
Jun 10, 2025
Join Chris Hutchins, creator of All the Hacks, as he shares his expertise on travel, money, and life optimization. Learn how to fly to Japan for just $222 and flip Costco gold into luxurious trips. Chris discusses strategies to maximize airline loyalty points and the importance of smart planning to avoid the optimizer’s curse—overthinking travel plans. He also dives into the world of travel rewards, credit card arbitrage, and maintaining balance in the pursuit of enriching experiences. Tune in for actionable tips and hilarious anecdotes!
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Gift Card Arbitrage Story

  • Chris Hutchins bought $1.02 million worth of Amazon gift cards at a discount using a creative app strategy.
  • He then sold these gift cards to customers at a profit while they saved money on Amazon purchases.
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Use Tools for Points Redemption

  • Use tools like Award Tool and Points Yeah to find optimal point redemptions for travel.
  • Being flexible with dates and destinations maximizes the value of your points.
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Loyalty Programs are Huge Assets

  • Airline loyalty programs often have a market cap larger than the airline companies themselves.
  • Airlines primarily operate as banks for miles and points rather than just aviation services.
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