Page de couverture de #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

#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

#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

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 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 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.*For show notes and past guests on The Tim Ferriss Show, please visit tim.blog/podcast.For deals from sponsors of The Tim Ferriss Show, please visit tim.blog/podcast-sponsorsSign up for Tim’s email newsletter (5-Bullet Friday) at tim.blog/friday.For transcripts of episodes, go to tim.blog/transcripts.Discover Tim’s books: tim.blog/books.Follow Tim:Twitter: twitter.com/tferriss Instagram: instagram.com/timferrissYouTube: youtube.com/timferrissFacebook: facebook.com/timferriss LinkedIn: ...

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