Navigating the Maze of Points and Miles

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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Past guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, Margaret Atwood, Mark Zuckerberg, Peter Thiel, Dr. Gabor Maté, Anne Lamott, Sarah Silverman, Dr. Andrew Huberman, and many more.

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