Podcast
291
Aug. 19, 2026
The Science of Lasting Happiness with Arthur Brooks
#291: Behavioral social scientist Arthur Brooks joins Chris to reveal why success and happiness follow different rules as we age. They dig into fluid vs. crystallized intelligence, success addiction and dopamine, the reverse bucket list, and how to actually buy happiness. Arthur C. Brooks is a Harvard Professor, musician, and columnist for the Atlantic, where he writes the weekly "How to Build a Life" column. He is the bestselling author of numerous books on happiness and human flourishing. Li...
290
Aug. 12, 2026
The New Rules of Points & Miles in 2026 with Brian M
#290: Chris and Brian break down the biggest trends reshaping points and miles. They discuss new ways to earn transferable points without a credit card, the award search tools worth using right now, a six-month check-in on Bilt, and what's coming next for premium cards. Link to Full Show Notes: https://chrishutchins.com/new-rules-points-miles-2026/ Partner Deals DeleteMe: 20% off removing your personal info from the web NetSuite: Free KPI checklist to upgrade your business performance Fora:...
289
Aug. 5, 2026
How We Booked a $20,000 Vacation With Points
Chris and Amy booked a last-minute week in Bora Bora that would have cost over $20,000, almost entirely on points. They break down how it came together, why they chose Bora Bora over Fiji, the Marriott award search quirk that hid available rooms, flying business class in both directions by mixing two airlines, and using card travel credits on the inter-island flights. Then, three nights in, they decided to abandon the deal and pay more to switch resorts. They compare and rank the major Bora Bora...
288
July 22, 2026
Where to Keep Your Cash for the Highest Return
#288: Chris breaks down exactly where to park your cash to earn the most, whether you have $10,000 or a few million. From high-yield savings accounts and Treasury ETFs to brokerage bonuses and cash management accounts, he explains the tradeoffs that actually matter—and why the highest advertised interest rate isn't always the best choice. He also shares the interactive tool he built to compare nearly 100 cash options based on your specific situation. Link to Full Show Notes: https://chrishutchi...
287
July 15, 2026
Putting Die With Zero Into Practice with Brad Barrett
#287: Chris and Brad Barrett revisit "Die With Zero" and confront how much harder Bill Perkins' ideas are to live than to agree with. They dig into when frugality flips from superpower to liability, the maximizer's struggle to let go, optimizing for the perfect Tuesday over the once-a-year trip, and giving money to your kids while it still matters. Brad is the co-host of the ChooseFI podcast and co-author of Choose FI: Your Blueprint to Financial Independence. Link to Full Show Notes: https://...
286
July 8, 2026
Are Credit Card Points Still Worth It? and More Listener Q&A
#286: With credit card fees climbing, credits getting harder to use, and points constantly devaluing, it's fair to ask whether earning points and miles is even worth it anymore. In this AMA, Chris breaks down why the fees are still worth it for him (and who they're not worth it for), common mistakes to avoid when running the numbers, and when cash back makes the most sense. He also walks through how to start from scratch, when a high annual fee actually pays for itself, and how to squeeze more o...
285
June 30, 2026
0285 - Die With Zero Replay
#285: Bill Perkins joins Chris to unpack what dying with zero really means in practice. They discuss why net fulfillment matters at every stage of life, which experiences are worth prioritizing now, how to bank memory dividends, the questions to ask yourself before spending (or saving), and how to solve for maximum fulfillment. Bill Perkins is a hedge fund manager, energy trader, and author of the international bestseller Die With Zero: Getting All You Can from Your Money and Your Life. Link t...
284
June 24, 2026
20+ Credit Card Benefits You’re Probably Not Using
#284: Chris breaks down the credit card benefits that save real money but rarely get attention, from getting a cracked iPhone repaired for free to purchase protections, travel coverage, and a deep bench of lesser-known perks. Learn exactly which card to reach for on every purchase, so you're always covered and never leaving money on the table. Link to Full Show Notes: https://chrishutchins.com/hidden-credit-card-benefits-2026/ Partner Deals Fora: Become a Fora Advisor today Bilt Rewards: Earn...
283
June 17, 2026
Do You Actually Need Travel Insurance?
#283: Learn exactly when you might need travel insurance and when your credit cards already have you covered. Chris breaks down what travel insurance covers, how those benefits compare to the coverage built into popular credit cards, and when it makes sense to buy additional protection. Plus, what US health insurance actually covers abroad, and specialty policies worth getting for medical evacuation, scuba diving, and trips off the beaten path. Link to Full Show Notes: https://www.chrishutchins...
282
June 10, 2026
Saving Money and Optimizing is My Kryptonite
#282: When does optimization stop helping and start hurting? Chris shares how a string of seemingly smart decisions had him pouring hours into marginal gains that never materialized. He unpacks the hidden cost of optimization, the role AI plays in amplifying it, and how he's learning to focus on what actually moves the needle. Link to Full Show Notes: https://chrishutchins.com/optimizing-is-my-kryptonite/ Partner Deals NetSuite: Free KPI checklist to upgrade your business performance Superhum...
281
June 3, 2026
Taking My Health Into My Own Hands: Tests, Records, and What Actually Worked
#281: Chris shares the full playbook he used to take control of his health after digging into his family historical and lab results. He breaks down which tests are actually worth your money and when each one matters. Plus, how he built a personal health AI from his own medical records to surface what doctors missed. Link to Full Show Notes: https://chrishutchins.com/personal-health-ai-diagnostics/. Partner Deals DeleteMe: 20% off removing your personal info from the web Fora: Become a Fora Ad...
280
May 27, 2026
The Hidden Rules of Credit Card Approvals
#280: Learn how to dramatically improve your odds of getting approved for the credit cards you actually want. Chris breaks down the hidden system every bank uses to evaluate applications, why your credit score matters far less than what's on your report, and the real factors driving denials, from credit-to-income ratios to recent inquiries to each issuer's internal model. He also walks through what to do before you apply, how to sequence applications across issuers, and the right moves to make a...
279
May 20, 2026
How Long-Term Investors Actually Think About Risk with Ben Carlson
#279: Learn to handle market volatility and build long-term wealth in a world dominated by AI disruption, market fear, inflation concerns, and nonstop financial noise. Chris and Ben discuss why investing remains psychologically difficult, how to think about global diversification, when to reevaluate your portfolio, and the risks most investors still overlook. Ben Carlson is the Director of Institutional Asset Management at Ritholtz Wealth Management and the author of five books on investing, in...
278
May 13, 2026
The AI Tools I'm Building to Replace My Spreadsheets with Anish Acharya
#278: Is AI making it possible for the average person to live a fully optimized life? Chris and Anish swap notes on how custom AI tools are replacing years of spreadsheets, and reshaping the way we work, learn, create, and relate to each other. They dig into why Chris has abandoned OpenClaw, the architecture mistakes almost everyone is making, and what happens when the subsidies on all these tools eventually go away. Anish Acharya is a general partner at Andreessen Horowitz, where he leads cons...
277
May 6, 2026
The Japan ER Visit That Changed How We Travel (& Tokyo Disney) with Amy Fox
#277: The last morning of our Japan trip turned into a sprint to a Tokyo emergency room, and challenged what we thought we knew about traveling abroad. We break down what a Japanese ER really cost, credit card benefits most travelers don't know they have, the best places to shop in Japan right now, and how to navigate Disney Tokyo without losing your day to four-hour lines. Link to Full Show Notes: https://chrishutchins.com/japan-er-disney-shopping Partner Deals Copilot Money: Free 2 months a...
276
April 29, 2026
Saving $30K+ on the Perfect Spring Break Japan Trip with Amy Fox
#276: Learn how Chris and Amy booked four nonstop business class seats and a week at the Park Hyatt Tokyo almost entirely on points. They break down the strategy, key takeaways for traveling with kids, Chris' AI-powered trip planner, and . Link to Full Show Notes: https://chrishutchins.com/50k-japan-trip-on-points Partner Deals Upwork: Free job posting to find, hire, and pay top freelance talent Wispr Flow: Try effortless voice dictation for free Fora: Become a Fora Advisor today MasterClass...
275
April 22, 2026
The Custom Everything Era with Kevin Rose
#275: Chris and Kevin dig into how they're actually using AI tools in their daily lives right now. They explore real-world AI use cases, the tradeoffs of sharing personal data, the collapse of trust online, and what all of this means for jobs, creativity, and human connection. Kevin Rose is the host of Diggnation and a partner at True Ventures, an early-stage venture capital firm that has invested over $4 billion in a portfolio of over 400+ founders. Kevin previously founded Zero and Oak, and w...
274
April 15, 2026
The Surprising History of Points and Miles
#274: Chris walks through the complete history of points and miles and breaks down the $140 billion machine behind them, so you can get more out of every point you earn. He covers the legal accidents that made credit cards wildly profitable, why loyalty programs are worth more than the airlines, the psychology behind why you keep hoarding points, and more. Link to Full Show Notes: https://chrishutchins.com/history-of-points-and-miles Partner Deals Storyworth: Share your mother's stories in a c...
273
April 8, 2026
Stop Overthinking and Start Deciding with Derek Sivers
#273: Learn to stop overthinking and make better decisions. Chris and Derek discuss how optimizing can go wrong, a coin flip trick for making decisions, journaling as a superpower, how your actions might reveal what you actually want, and more. Derek Sivers is an entrepreneur, writer, and self-proclaimed "slow thinker" best known for founding CD Baby, which he sold for $22M and gave the proceeds to charity. He’s since dedicated his life to creating, learning, and writing books like Hell Yeah or...
272
April 1, 2026
My Process for Booking Travel with Points & Miles
#272: Learn how to turn your points into significantly better travel experiences by following a simple, repeatable system. We cover how to plan, find award availability, choose the right tools, and decide between portals vs. transfers, plus the mindset shifts that make the whole process work. Link to Full Show Notes: https://chrishutchins.com/booking-travel-with-points-and-miles-2026 Partner Deals Gelt: Skip the waitlist on personalized tax guidance to maximize your wealth Bilt Rewards: Earn...
271
March 25, 2026
How to Actually Live the Life You're Optimizing For with Sahil Bloom
#271: Learn why over-optimizing your life can quietly destroy the things you actually care about. Chris and Sahil explore the doorman fallacy, why big life decisions should happen fast, how to use AI as a thinking partner, and why systems beat motivation every time. Sahil Bloom is a writer, entrepreneur, and investor. He wrote The 5 Types of Wealth, publishes the newsletter The Curiosity Chronicle to nearly a million readers, and is the Founder of the men's skincare line Wild Roman. Link to Fu...
270
March 18, 2026
Ski Trip Mishaps, AI Interior Design, Reflecting on Life and More
#270: Chris and Amy discuss lessons from three ski trips with kids, using AI to redesign rooms on a budget, their favorite new gadgets, navigating high-deductible health plans, and more. Link to Full Show Notes: https://chrishutchins.com/ski-trips-ai-home-design-health-finances-amy Partner Deals NetSuite: Free KPI checklist to upgrade your business performance Gelt: Skip the waitlist on personalized tax guidance to maximize your wealth Trust & Will: Get 20% off personalized, legally binding es...
269
March 11, 2026
Inside My 300K Point Transfer, Hyatt's Devaluation, Future of AI Agents & More
#269: Chris breaks down why he transferred >200k points for a transfer bonus and how to know when they're actually worth it. He also covers Hyatt's new award chart changes, the latest elevated welcome offers, and how he's using multiple AI agents to optimize his work and life. Link to Full Show Notes: https://chrishutchins.com/transfer-bonuses-hyatt-devaluation-ai Partner Deals Copilot Money: Free 2 months access to my favorite personal finance app with code HACKS2 Fabric: Affordable term life...
266
March 4, 2026
Stop Planning, Start Experimenting: A Science-Backed Approach to a Better Life with Anne-Laure Le Cunff
#268: Learn why setting big goals might actually be holding you back and what to do instead. Chris and Anne-Laure explore how to replace goal-setting with tiny, low-risk experiments that lead to more growth, more joy, and less burnout. Anne-Laure Le Cunff is a neuroscientist, writer, and founder of Ness Labs, a learning community at the intersection of science and self-development. She is the author of Tiny Experiments and publishes a weekly newsletter on mindful productivity, creativity, and g...