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)

“There’s something fun about knowing you kind of ‘got one’ over the system.”
— Chris Hutchins

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.

Please enjoy!

Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Castbox, YouTube Music, Amazon Music, Audible, or on your favorite podcast platform. Watch the interview on YouTube.

This episode is brought to you by AG1 all-in-one nutritional supplement; Shopify global commerce platform, providing tools to start, grow, market, and manage a retail business; and Ramp easy-to-use corporate cards, bill payments, accounting, and more.

Listen onApple Podcasts

Listen onSpotify

Listen onOvercast

This episode is brought to you by Ramp! Ramp is corporate card- and spend-management software designed to help you save time and put money back in your pocket. Ramp has already saved more than 25,000 customers—including other podcast sponsors like Shopify and Eight Sleep—more than 10 million hours and more than $1 billion through better financial management of their corporate spending.

With Ramp, you’re able to issue cards to every employee with limits and restrictions and automate expense reporting, allowing you to close your books 8x faster on average. Your employees will no longer need to spend hours submitting expense reports. In less than 15 minutes, you can get started issuing virtual and physical cards and making payments, whether you have 5 employees or 5,000. Businesses that use Ramp save an average of 5% on total card spending and related expenses in the first year. And now, you can get $250 when you join Ramp. Just go to ramp.com/Tim.

This episode is brought to you by AG1! I get asked all the time, “If you could use only one supplement, what would it be?” My answer is usually AG1, my all-in-one nutritional insurance. I recommended it in The 4-Hour Body in 2010 and did not get paid to do so. I do my best with nutrient-dense meals, of course, but AG1 further covers my bases with vitamins, minerals, and whole-food-sourced micronutrients that support gut health and the immune system. 

Right now, you’ll get a 1-year supply of Vitamin D free with your first subscription purchase—a vital nutrient for a strong immune system and strong bones. Visit DrinkAG1.com/Tim to claim this special offer today and receive your 1-year supply of Vitamin D (and 5 free AG1 travel packs) with your first subscription purchase! That’s up to a one-year supply of Vitamin D as added value when you try their delicious and comprehensive daily, foundational nutrition supplement that supports whole-body health.

This episode is brought to you by Shopify! Shopify is one of my favorite platforms and one of my favorite companies. Shopify is designed for anyone to sell anywhere, giving entrepreneurs the resources once reserved for big business. In no time flat, you can have a great-looking online store that brings your ideas to life, and you can have the tools to manage your day-to-day and drive sales. No coding or design experience required.

Go to shopify.com/Tim to sign up for a one-dollar-per-month trial period. It’s a great deal for a great service, so I encourage you to check it out. Take your business to the next level today by visiting shopify.com/Tim.

Want to hear the last time Chris came on the show to help our audience’s aspiring podcasters get started on the right foot? Listen to our conversation here in which we discussed contingency plans for inevitable technical SNAFUs, gear we use, pros and cons of recording a podcast on video, prioritizing good guests over well-known guests, the magic of recording long and editing liberally for fixing imperfect sessions, the painful but positive effects of soliciting feedback, prep tips, how to be of the best service to yourself and your audience, and much more.

What was your favorite quote or lesson from this episode? Please let me know in the comments.

SELECTED LINKS FROM THE EPISODE

• Connect with Chris Hutchins:

All the Hacks

Online Tools & Resources

• All the Hacks: Chris’ primary website for his podcast and resources.
• Annual Credit Report: the official, government-authorized website for free credit reports.
• AwardTool: a tool for searching for award flights using points and miles.
• Booking.com: online travel agency for booking accommodations, flights, etc.
• Bureau of Labor Statistics: US government agency providing economic data, including consumer spending.
• Pure: a marketplace for gold and other collectibles.
• Credit Karma: a website and app offering free credit scores and reports.
• Expedia: online travel agency.
• Google Flights: a flight search engine.
• Miles4Migrants: defunct program that used donated points to fly migrants to safety.
• Points Path: a browser extension for Google Flights that shows points redemption options.
• PointsYeah: a tool for searching award flights, featuring a “Daydream Explorer.”
• Rooms.aero: a tool for searching hotel award availability.
• Seats.aero: a tool for searching award flight availability, often presented in a spreadsheet-like format.
• Apple Pay: mobile payment service by Apple.
• ChatGPT: AI language model.
• Pepper: a gift card app upgraded to an AI personal shopper.

Books

• Die With Zero: Getting All You Can from Your Money and Your Life by Bill Perkins
• Happy Money: The Science of Happier Spending by Elizabeth Dunn and Michael Norton
• From Strength to Strength: Finding Success, Happiness, and Deep Purpose in the Second Half of Life by Arthur C. Brooks
• The 4-Hour Body: An Uncommon Guide to Rapid Fat-Loss, Incredible Sex, and Becoming Superhuman by Timothy Ferriss
• The 4-Hour Chef: The Simple Path to Cooking Like a Pro, Learning Anything, and Living the Good Life by Timothy Ferriss
• The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich by Timothy Ferriss
• The Art of Spending Money: Simple Choices for a Richer Life by Morgan Housel
• The Man Who Quit Money by Mark Sundeen
• The Psychology of Money: Timeless Lessons on Wealth, Greed, and Happiness by Morgan Housel
• The 5 Types of Wealth: A Transformative Guide to Design Your Dream Life by Sahil Bloom

Financial Institutions & Services

• Amex (American Express): an American bank holding company and multinational financial services corporation that specializes in payment cards.
• Aetna: a major American health insurance company that provides medical, pharmaceutical, dental, behavioral health, and long-term care benefits.
• Bank of America: one of the largest banks in the United States, offering consumer and commercial banking, wealth management, and investment services.
• Capital One: an American bank holding company specializing in credit cards, auto loans, banking, and savings accounts.
• Charles Schwab: a major American multinational financial services company offering brokerage, banking, and financial advisory services.
• Citibank: the consumer division of Citigroup, one of the largest banks in the world, providing retail banking services globally.
• Fidelity: a multinational financial services corporation offering investment management, retirement planning, portfolio guidance, and brokerage services.
• MasterCard: a multinational financial services corporation that operates a global payment network for electronic payments.
• Merrill Lynch: a wealth management division of Bank of America providing investment, insurance, and retirement planning services.
• Morgan Stanley: an American multinational investment bank and financial services company offering securities, asset management, and wealth management.
• PAMP: a Swiss precious metals refining company and one of the world’s leading bullion brands for gold, silver, platinum, and palladium products.
• Robinhood: a commission-free trading platform that allows users to invest in stocks, ETFs, options, and cryptocurrencies through a mobile app.
• Square: a financial services and payment processing company (now part of Block, Inc.) that provides payment solutions for businesses and individuals.
• Stripe: an online payment processing platform that enables businesses to accept payments over the internet and manage online transactions.
• US Bank: the fifth-largest commercial bank in the United States, offering banking, investment, mortgage, trust, and payment services.
• Visa: a multinational financial services corporation that facilitates electronic funds transfers through its payment network worldwide.
• Wealthfront: an automated investment service (robo-advisor) that provides portfolio management, financial planning, and cash management services.
• Wells Fargo: a major American multinational financial services company offering banking, investment, mortgage, and consumer finance services.

Airlines & Airline Alliances

• Air Canada: Canada’s flag carrier and largest airline, offering domestic and international flights with hubs in Toronto, Vancouver, and Montreal.
• Air France: the flag carrier of France and a founding member of the SkyTeam alliance, operating from its main hub at Charles de Gaulle Airport in Paris.
• Alaska Airlines: a major American airline based in Seattle, known for its extensive West Coast network and strong customer service reputation.
• ANA (All Nippon Airways): Japan’s largest airline and a Star Alliance member, renowned for its exceptional service quality and extensive domestic and international network.
• American Airlines: one of the largest airlines in the world and a founding member of the Oneworld alliance, with major hubs across the United States.
• Delta Air Lines: a major American airline and founding member of the SkyTeam alliance, with its largest hub at Hartsfield-Jackson Atlanta International Airport.
• Emirates: the flag carrier of the United Arab Emirates based in Dubai, known for its luxury service and extensive international network connecting six continents.
• Japan Airlines: Japan’s flag carrier and a Oneworld alliance member, offering domestic and international flights with a focus on premium service and hospitality.
• JetBlue: a low-cost American airline known for its customer service, free Wi-Fi, and comfortable seating on domestic and select international routes.
• Lufthansa: Germany’s flag carrier and a founding member of the Star Alliance, operating from major hubs in Frankfurt and Munich.
• Oneworld Alliance: a global airline alliance founded in 1999, comprising major carriers like American Airlines, British Airways, and Cathay Pacific.
• SkyTeam Alliance: a global airline alliance founded in 2000, including member airlines such as Delta, Air France-KLM, and Korean Air.
• Southwest Airlines: a major American low-cost airline known for its point-to-point service model, free checked bags, and no change fees policy.
• Star Alliance: the world’s largest global airline alliance founded in 1997, with member airlines including United, Lufthansa, and Singapore Airlines.
• TAP Air Portugal: Portugal’s flag carrier and a Star Alliance member, serving as a gateway between Europe, Africa, and the Americas from its Lisbon hub.
• United Airlines: a major American airline and founding member of the Star Alliance, with significant hubs in Chicago, Denver, Houston, and San Francisco.

Hotels & Hospitality Brands

• Cap Rocat (Majorca): a luxury fortress hotel in Mallorca, Spain, converted from a 19th-century military fortress offering exclusive accommodations with Mediterranean views.
• Conrad Hotels & Resorts: Hilton’s luxury hotel brand offering sophisticated accommodations and personalized service in major business and leisure destinations worldwide.
• Four Seasons Hotels and Resorts: a Canadian luxury hotel and resort company known for exceptional service, elegant accommodations, and properties in premier destinations globally.
• Hilton Hotels & Resorts: a global hospitality company and flagship brand offering full-service hotels, resorts, and suites with comprehensive amenities for business and leisure travelers.
• Hyatt Hotels Corporation: an American multinational hospitality company operating luxury, premium, and select service hotels and resorts worldwide with various brand portfolios.
• Marriott Bonvoy: Marriott International’s loyalty program and hotel portfolio, encompassing 30+ brands from luxury to extended-stay properties across the globe.
• Miraval Resorts: a collection of luxury wellness resorts focused on mindful living, spa treatments, fitness, and holistic wellness experiences in scenic destinations.
• Nobu: a luxury lifestyle brand combining world-class hospitality with the culinary expertise of Chef Nobu Matsuhisa, offering hotels and restaurants worldwide.
• Small Luxury Hotels of the World (SLH): a collection of more than 520 independent luxury hotels worldwide, each offering unique character and exceptional personalized service.
• Waldorf Astoria Hotels & Resorts: Hilton’s ultra-luxury hotel brand providing iconic accommodations and legendary service in the world’s most sought-after destinations.

Retail & Other Brands

• Amazon: the world’s largest e-commerce and cloud computing company, offering everything from retail products to digital services and logistics solutions.
• Amazon Fresh: Amazon’s online and physical grocery delivery service providing fresh produce, pantry items, and household essentials with same-day or next-day delivery.
• Apple: a multinational technology company known for innovative consumer electronics, software, and digital services including iPhone, Mac, iPad, and Apple Watch.
• Costco: a membership-based warehouse club offering bulk quantities of groceries, electronics, and household items at discounted prices to members.
• Dick’s Sporting Goods: a leading American sporting goods retailer offering athletic equipment, apparel, and footwear for various sports and outdoor activities.
• FedEx: a multinational courier delivery and logistics company providing express shipping, ground delivery, freight, and supply chain management services worldwide.
• Goodwill Industries: a nonprofit organization operating thrift stores that sell donated goods to fund job training, employment placement, and community programs.
• Healthy Choice: a food brand owned by Conagra Brands, specializing in frozen meals, soups, and snacks marketed as healthier alternatives with reduced sodium and calories.
• Lowe’s: a major American home improvement retailer offering tools, appliances, building materials, and services for home renovation and maintenance projects.
• Spotify: a Swedish music streaming platform providing access to millions of songs, podcasts, and playlists with both free and premium subscription options.
• US Mint (United States Mint): the official government agency responsible for producing and distributing coins, commemorative coins, and precious metal products for the United States.
• Whole Foods Market: an upscale grocery chain owned by Amazon, specializing in organic, natural, and high-quality foods with a focus on health and sustainability.

Credit Cards & Memberships

• Amex Business Gold Card: a premium business credit card offering 4x points on top spending categories and valuable business benefits with flexible payment options.
• Amex Business Platinum Card: American Express’s flagship business credit card providing premium travel benefits, airport lounge access, and substantial rewards for business expenses.
• Amex Gold Card: a premium personal credit card offering 4x points on dining and groceries, plus valuable dining and travel credits for cardholders.
• Amex Platinum Card: American Express’s flagship personal credit card featuring luxury travel benefits, airport lounge access, hotel elite status, and premium concierge services.
• Bank of America Premium Rewards Card: a premium travel rewards credit card offering bonus points on travel and dining, with enhanced benefits for Preferred Rewards members.
• Bank of America Unlimited Cash Rewards / Travel Rewards Card: cash back and travel rewards cards that offer enhanced earning rates and benefits when paired with Bank of America’s Preferred Rewards program.
• Capital One Spark Cash Card: a straightforward business credit card offering unlimited 2% cash back on all purchases with no spending categories or caps.
• Capital One Venture Card: a travel rewards credit card offering 2x miles on every purchase with flexible redemption options and travel benefits.
• Capital One Venture X Business Card: a premium business travel rewards card offering enhanced earning rates, travel credits, and Priority Pass lounge access for business travelers.
• Capital One Venture X Card: Capital One’s flagship travel rewards card featuring premium travel benefits, annual travel credits, and Priority Pass lounge access.
• Chase Freedom / Freedom Flex Cards: popular cash back credit cards offering rotating 5% bonus categories and flat-rate cash back on everyday purchases.
• Chase Ink Business Preferred Card: a premium business credit card offering 3x points on select business categories and valuable Ultimate Rewards earning potential.
• Chase Sapphire Preferred Card: a popular travel rewards credit card offering enhanced earning on travel and dining with flexible Ultimate Rewards redemption options.
• Costco Executive Membership: Costco’s premium membership tier offering 2% annual reward on qualifying Costco purchases plus additional benefits and exclusive offers.
• Delta Reserve Amex Card: a premium co-branded credit card offering Delta elite status benefits, Sky Club access, and enhanced earning on Delta purchases and travel.
• Fidelity Rewards Visa Signature Card: a straightforward rewards credit card offering 2% cash back on all purchases that can be deposited directly into Fidelity investment accounts.
• Robinhood Gold Card: a cash back credit card integrated with Robinhood’s investment platform, offering 3% cash back on select categories and investment-focused benefits.
• Southwest Airlines Companion Pass: Southwest’s premier membership benefit allowing a designated companion to fly free (minus taxes and fees) on all Southwest flights for qualifying members.
• US Bank Four Percent Cash Back Card: a high-yield cash back credit card offering 4% cash back on select categories, though availability and terms may have changed or been discontinued.

Concepts

• Four Percent Rule (Retirement withdrawal strategy): a retirement planning guideline suggesting that retirees can safely withdraw 4% of their portfolio annually, adjusted for inflation, without running out of money over a 30-year period.
• Arbitrage: the practice of taking advantage of price differences between markets to buy and sell identical or similar financial instruments simultaneously for risk-free profit.
• Cash Back Rewards: a credit card benefit that returns a percentage of purchase amounts to cardholders as cash, typically ranging from 1% to 5% depending on spending categories.
• Coast FI / Coast FIRE (Financial Independence, Retire Early concept): a variation of FIRE where individuals have saved enough that compound growth will fund their retirement without additional contributions, allowing them to “coast” with lower savings rates.
• Dunning-Kruger Effect: a cognitive bias where people with limited knowledge or competence in a domain overestimate their own knowledge or competence in that domain.
• FICO Score: the most widely used credit scoring model in the United States, ranging from 300 to 850, used by lenders to assess creditworthiness and loan risk.
• Fisherman Parable: a parable about work-life balance where a businessman advises a fisherman to expand his business, only to learn the fisherman already enjoys the lifestyle the businessman is working toward.
• FIRE (Financial Independence, Retire Early) Movement: a lifestyle movement focused on extreme savings and investing to achieve financial independence and early retirement, typically by saving 50-70% of income.
• Interchange Fees: transaction fees that merchants pay to card-issuing banks when customers use credit or debit cards, typically ranging from 1.5% to 3.5% of the transaction amount.
• Loyalty Programs / Points & Miles: marketing strategies that reward customers for repeat business through points, miles, or other benefits that can be redeemed for products, services, or travel.
• Memory Dividends: Bill Perkins’ concept that experiences create lasting memories that continue to provide value and happiness long after the money spent, unlike financial dividends.
• Money Rules: Ramit Sethi’s personal finance philosophy emphasizing automation, conscious spending on things you love, and cutting costs ruthlessly on things you don’t care about.
• Net Fulfillment vs. Net Worth: Bill Perkins’ framework suggesting that maximizing life fulfillment and experiences should take priority over simply accumulating wealth, especially in later years.
• Optimizer’s Curse: a cognitive bias where people who extensively research and optimize decisions often end up less satisfied with outcomes due to inflated expectations and analysis paralysis.
• Orthorexia: a term that describes an obsession with eating healthy food. It comes from the Greek words ortho, meaning ‘correct’ and orexis, meaning ‘appetite’.
• Trough of Sorrow: a startup development phase characterized by declining initial enthusiasm, user engagement challenges, and the difficult period between launch excitement and sustainable growth.
• VantageScore: an alternative credit scoring model developed by the three major credit bureaus, ranging from 300 to 850, designed to compete with FICO scores in credit assessment.

Legislation & Government Entities/Programs

• Credit Card Competition Act: proposed federal legislation aimed at increasing competition in the credit card processing market by requiring large banks to offer multiple payment network options beyond Visa and Mastercard.
• Crypto GENIUS Act: proposed federal legislation designed to establish a comprehensive regulatory framework for cryptocurrency and blockchain technology, providing clarity for businesses and consumers in the digital asset space.
• US Mint $1 Coin Program: various United States Mint programs that have produced commemorative and circulating dollar coins, including the Presidential $1 Coin Program and American Innovation $1 Coin Program.

Podcasts

• All the Hacks with Chris Hutchins
• Point Me To First Class with Devon Gimbel
• The Peter Attia Drive Podcast

People

• Mike Tyson
• Kevin Rose
• Tom Hanks
• Marie Kondo
• Dave Phillips
• Brad Wilson
• J. Kyle Bass
• Chris Sacca
• Chad Janis
• Hannah Janis
• Bill Perkins
• Devon Gimbel
• Amy Fox
• John Arnold
• Peter Attia
• Sahil Bloom
• Morgan Housel
• Arthur C. Brooks
• Mark Sundeen
• Daniel Suelo
• Ramit Sethi

SHOW NOTES

• [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.

MORE CHRIS HUTCHINS QUOTES FROM THE INTERVIEW

“I’ve always been thinking in the back of my head, ‘How do I do the thing that everyone else with all this money and all these resources does? How do I get to do that, even though I don’t have the resources?’ So that’s been my MO for life: I don’t want to sacrifice, but I also don’t want to go into debt or just spend money I don’t have.”
— Chris Hutchins

“Sometimes it just feels good to take a free trip. Who cares if it’s a good deal? You went on a trip you weren’t going to take otherwise.”
— Chris Hutchins

“Everyone listening should not be getting less than two points or two percent on any transaction, because you’re just giving money away.”
— Chris Hutchins

“There’s something fun about knowing you kind of ‘got one’ over the system.”
— Chris Hutchins

“I’m not going to let an AI book my travel, but I might let it do some exploration.”
— Chris Hutchins

“If you think too much about money, you just lose sight of the fact that money is a tool to help you achieve things. And if you don’t have any, it’s a really important tool, but as you have more, sometimes it just becomes a thing that you focus on way too much. And if you can learn to be happy with whatever you have, you might not need to chase. And that chasing is so toxic.”
— Chris Hutchins

The post 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) appeared first on The Blog of Author Tim Ferriss.