#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

Chris Hutchins is the creator and host of All the Hacks, a podcast that helps people upgrade their life, money, and travel. He previously founded Grove (acquired by Wealthfront) and Milk (acquired by Google), led New Product Strategy at Wealthfront, and was a Partner at Google Ventures. Most importantly, he is the person Kevin Rose and I call if we want to figure how to get a better deal on just about anything in the world, or if we just want to learn about his latest hijinks doing things like getting $200 flights to Japan, running gold pseudo-arbitrage at retail, or dirt-cheap trips to Bora Bora. We cover all three and more in this conversation. Sponsors: Shopify global commerce platform, providing tools to start, grow, market, and manage a retail business: https://shopify.com/tim (one-dollar-per-month trial period) Ramp easy-to-use corporate cards, bill payments, accounting, and more: https://ramp.com/tim (Get $250 when you join Ramp) AG1 all-in-one nutritional supplement: https://DrinkAG1.com/Tim (1-year supply of Vitamin D (and 5 free AG1 travel packs) with your first subscription purchase.) Timestamps: [00:00:00] Curses! COVID again. (Start.) [00:00:32] Meet Chris Hutchins: master of All the Hacks. [00:06:22] Coping with a Frankenstein’s Monster of travel points. [00:10:27] How did Chris become obsessed with the art of arbitrage? [00:12:18] Flipping gift cards for fun and profit. [00:17:17] The mechanics of Costco gold arbitrage. [00:22:31] Using AwardTool for finding point deals. [00:25:19] Daydream exploring with PointsYeah. [00:27:27] Why do modern airlines rely on loyalty programs to survive? [00:33:22] Chris maps out the different kinds of points and how to optimize them. [00:36:22] My inner struggle: hoard vs. spend. [00:37:55] Creative uses for large point balances. [00:41:20] Cash back card alternatives. [00:44:14] Chris analyzes the value of my 12 million Amex points. [00:46:23] 200 hotel nights or 150 business class flights? [00:4