#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, 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-sponsors


Sign 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/timferriss


YouTube: youtube.com/timferriss


Facebook: facebook.com/timferriss 


LinkedIn: linkedin.com/in/timferriss


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.


See Privacy Policy at https://art19.com/privacy and California
Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.