Podcast

#297: Learn how to turn small talk, awkward encounters, and everyday logistics into conversations that actually matter. Chris and Vanessa explore the chemistry behind great conversations, how to find the topics that make people light up, and the three levels of conversation that lead to deeper connection. Vanessa Van Edwards is a behavioral researcher, bestselling author of Captivate and Cues, and founder of Science of People. She teaches at Harvard, and her new book, Conversation: How to Conne...

#296: You're probably overpaying for cell service, and switching could save you hundreds of dollars a year without sacrificing coverage or features. Chris breaks down what's changed with the big carriers and MVNOs, the math behind "free phone" deals, the few features only AT&T, Verizon and T-Mobile still offer, and his shortlist of the best unlimited plans. He also shares the cheapest backup line for two-factor texts, a $20 home internet backup, how to think about cell phone insurance, and the s...

#295: Chris shares the strategies he actually uses to earn, spend, and maximize millions of points and miles. He breaks down how many credit cards most people really need, his approach to booking award travel for a family, the rise of massive card-member flight discounts, when to pay cash vs. points, and some of his favorite—and most unusual—redemptions. Meghan Coyle and Sally French are the hosts of NerdWallet's Smart Travel podcast, a weekly show on travel news, loyalty programs and travel cr...

#294: Chris breaks down everything he's learned going all in on World of Hyatt. He covers the brands and footprint, earning points with Hyatt credit cards and transfers, what points are really worth, every status tier and milestone reward, and how to get Globalist treatment without having status. Link to Full Show Notes: https://chrishutchins.com/world-of-hyatt-deep-dive/ Partner Deals ElevenLabs: Build an experience your customers will love Copilot Money: ⁠Free 2 months access to my favorite ...

#293: Learn to make your home healthier by focusing on the environmental factors that actually matter. Chris and Dom break down how to improve air and water quality, ventilation, mold prevention, lighting, and EMF exposure, plus what to prioritize in your bedroom, which popular healthy-home products to avoid, and the best upgrades at any budget. Dom Francks is the General Manager of Lightwork Home, a Stanford-trained engineer, and former climate-tech product leader. Link to Full Show Notes: ht...

#292: What happens to your points and miles when you die? And how can you make sure they don’t disappear? Chris breaks down how major banks, airlines, and hotel programs handle rewards after death, strategies to protect or transfer your points, and the steps you can take now to make things easier for your family. Plus, learn what to do if you’re already dealing with a loved one’s rewards, why documenting your accounts and logins matters, and the surprising rules around gift cards, divorce, and t...

#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: 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:...

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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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...