#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? [00:48:47] Seat availability challenges and alert rebooking strategies. [00:55:33] Making use of smaller airline point balances. [00:58:57] Non-travel uses for points. [01:02:26] Strategies for expiring points. [01:06:12] Flexible booking for maximum value. [01:07:12] Using Seats.aero for a Lufthansa first class and Frankfurt terminal experience. [01:10:45] Using Rooms.aero to find surprise hotel deals around the world. [01:11:51] Point strategies gone wrong and the optimizer’s curse. [01:14:36] Using Points Path with Google Flights to decide if a trip is worth the points. [01:15:30] The Dunning-Kruger curve of points hacking. [01:18:13] Escaping the optimization trap: when frugality becomes a burden. [01:21:33] What I could have done differently with my reward cards. [01:24:28] Points arbitrage: buying vs. earning. [01:27:01] Optimal reward cards for small business owners. [01:28:07] Status benefits and Southwest’s companion pass. [01:32:05] Pudding cups, $1 coins, and other heartwarming arbitrage tales. [01:36:47] How Chris saved $11,000 on his wedding by bartering with points. [01:38:53] Using points for employee/family gifts and business benefits. [01:42:09] How Chris would optimize point resources in my shoes. [01:45:16] The joy (and livelihood) Chris gets from sharing a day in his life. [01:46:57] Pondering AI’s future impact on travel, point optimization, regulatory changes, and itinerary planning. [01:53:56] Hotel relationship building through direct communication. [01:57:01] Insider restaurant hacks. [01:58:05] Credit card signup bonuses and credit score impact. [02:00:31] Card closure strategy and credit history preservation. [02:03:35] Amex Platinum Card evaluation and optimization. [02:06:12] Using government-sanctioned Annualcreditreport.com to monitor your credit report. [02:08:49] Spousal credit card strategy: doubling bonuses. [02:10:24] Chris’ travel enjoyment philosophy and spending mindset. [02:13:36] Paying cash vs. points at the Four Seasons Lanai. [02:15:08] Learni