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.

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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] Learning how to spend money as a frugal person.

[02:17:28] High-quality experiences over extreme optimization.

[02:18:38] Die with Zero: Bill Perkins and the money timing game.

[02:21:14] Coast FIRE (Financial Independence Retire Early).

[02:22:38] Recommended reading for developing a conscious, fulfilling relationship with money.

[02:25:47] The limits of universal financial advice.

[02:29:48] Chris’ potential alternative career paths.

[02:32:09] The fisherman parable and contentment.

[02:33:17] Parting thoughts.

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#815: Chris Hutchins, Deal Master — Help...