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
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