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:
[] Curses! COVID again. (Start.)
[] Meet Chris Hutchins: master of All the Hacks.
[] Coping with a Frankenstein’s Monster of travel points.
[] How did Chris become obsessed with the art of arbitrage?
[] Flipping gift cards for fun and profit.
[] The mechanics of Costco gold arbitrage.
[] Using AwardTool for finding point deals.
[] Daydream exploring with PointsYeah.
[] Why do modern airlines rely on loyalty programs to survive?
[] Chris maps out the different kinds of points and how to optimize them.
[] My inner struggle: hoard vs. spend.
[] Creative uses for large point balances.
[] Cash back card alternatives.
[] Chris analyzes the value of my 12 million Amex points.
[] 200 hotel nights or 150 business class flights?
[] Seat availability challenges and alert rebooking strategies.
[] Making use of smaller airline point balances.
[] Non-travel uses for points.
[] Strategies for expiring points.
[] Flexible booking for maximum value.
[] Using Seats.aero for a Lufthansa first class and Frankfurt terminal experience.
[] Using Rooms.aero to find surprise hotel deals around the world.
[] Point strategies gone wrong and the optimizer’s curse.
[] Using Points Path with Google Flights to decide if a trip is worth the points.
[] The Dunning-Kruger curve of points hacking.
[] Escaping the optimization trap: when frugality becomes a burden.
[] What I could have done differently with my reward cards.
[] Points arbitrage: buying vs. earning.
[] Optimal reward cards for small business owners.
[] Status benefits and Southwest’s companion pass.
[] Pudding cups, $1 coins, and other heartwarming arbitrage tales.
[] How Chris saved $11,000 on his wedding by bartering with points.
[] Using points for employee/family gifts and business benefits.
[] How Chris would optimize point resources in my shoes.
[] The joy (and livelihood) Chris gets from sharing a day in his life.
[] Pondering AI’s future impact on travel, point optimization, regulatory changes, and itinerary planning.
[] Hotel relationship building through direct communication.
[] Insider restaurant hacks.
[] Credit card signup bonuses and credit score impact.
[] Card closure strategy and credit history preservation.
[] Amex Platinum Card evaluation and optimization.
[] Using government-sanctioned Annualcreditreport.com to monitor your credit report.
[] Spousal credit card strategy: doubling bonuses.
[] Chris’ travel enjoyment philosophy and spending mindset.
[] Paying cash vs. points at the Four Seasons Lanai.
[] Learning how to spend money as a frugal person.
[] High-quality experiences over extreme optimization.
[] Die with Zero: Bill Perkins and the money timing game.
[] Coast FIRE (Financial Independence Retire Early).
[] Recommended reading for developing a conscious, fulfilling relationship with money.
[] The limits of universal financial advice.
[] Chris’ potential alternative career paths.
[] The fisherman parable and contentment.
[] Parting thoughts.
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