#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 (chrishutchins.com), a podcast that helps people upgrade their life, money, and travel. He previously founded Grove (hellogrove.com) (acquired by Wealthfront (wealthfront.com/tim)) and Milk (techcrunch.com/2012/03/15/winning-a-bidding-wa…) (acquired by Google), led New Product Strategy atWealthfront (wealthfront.com/tim), and was a Partner at Google Ventures (gv.com). Most importantly, he is the person Kevin Rose (youtube.com/playlist?list=PLuu6fDad2eJzyeAF4UH…) 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:
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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 (awardtool.com) for finding point deals.
[00:25:19] Daydream exploring with PointsYeah (pointsyeah.com).
[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 (seats.aero) for a Lufthansa first class and Frankfurt terminal experience.
[01:10:45] Using Rooms.aero (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 (pointspath.com) with Google Flights (google.com/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 (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 (tim.blog/podcast) include Jerry Seinfeld (tim.blog/2020/12/08/jerry-seinfeld), Hugh Jackman (tim.blog/2020/06/26/hugh-jackman), Dr. Jane Goodall (tim.blog/2020/04/16/jane-goodall), LeBron James (tim.blog/2018/11/27/lebron-james-mike-mancias), Kevin Hart (tim.blog/2020/05/20/kevin-hart), Doris Kearns Goodwin (tim.blog/2018/09/07/doris-kearns-goodwin-leade…), Jamie Foxx (tim.blog/2015/12/06/jamie-foxx), Matthew McConaughey (tim.blog/2020/10/19/matthew-mcconaughey), Esther Perel (tim.blog/2017/05/21/esther-perel), Elizabeth Gilbert (tim.blog/2020/05/08/elizabeth-gilbert), Terry Crews (tim.blog/2017/12/20/terry-crews-how-to-have-do…), Sia (tim.blog/2020/08/12/sia), Yuval Noah Harari (tim.blog/2020/10/27/yuval-noah-harari), Malcolm Gladwell (tim.blog/2016/06/21/malcolm-gladwell), Madeleine Albright (tim.blog/2020/05/27/secretary-madeleine-albright), Cheryl Strayed (tim.blog/2017/03/30/cheryl-strayed), Jim Collins (tim.blog/2019/02/18/jim-collins), Mary Karr, (tim.blog/2020/11/11/mary-karr) Maria Popova (tim.blog/2014/10/21/brain-pickings), Sam Harris (tim.blog/2020/05/15/sam-harris-2), Michael Phelps (tim.blog/2021/01/21/michael-phelps-grant-hackett), Bob Iger (tim.blog/2020/01/16/bob-iger), Edward Norton (tim.blog/2019/10/31/edward-norton-motherless-b…), Arnold Schwarzenegger (tim.blog/2015/02/02/arnold-schwarzenegger), Neil Strauss (tim.blog/2014/06/24/neil-strauss), Ken Burns (tim.blog/2019/09/12/ken-burns), Maria Sharapova (tim.blog/2017/08/26/maria-sharapova), Marc Andreessen (tim.blog/2016/05/29/marc-andreessen), Neil Gaiman (tim.blog/2019/03/28/neil-gaiman), Neil de Grasse Tyson (tim.blog/2019/10/03/neil-degrasse-tyson), Jocko Willink …