#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 arb