All the Hacks: Money, Points & Life

#300: Chris and Amy break down how they planned an unforgettable trip to Switzerland and Lake Como mostly on points, miles, and free-night certificates. They share how speculative bookings and award alerts landed them better business class flights, the rental car hack that avoided a cross-border drop-off fee, and one of the best uses of Hilton points around. Plus, an inside look at a fairy tale ho...

#299: My top 10 takeaways from a retreat for high-net-worth investors, which covered money, health, AI, parenting, relationships, and more. We explore why what you measure shapes your behavior, how to start using AI agents, why simple rules beat perfect plans, how to teach kids about money, and why “later” may be the most expensive word in your vocabulary. Tad Fallows is the co-founder of&nbs...

#298: Chris breaks down how to earn airline miles and transferable points on money you’re already saving or investing (and whether the rewards are actually worth the tradeoffs). He compares mileage-earning bank accounts from Bask, United and Alaska, the new Bank of America and Alaska transfer partnership, Silo’s brokerage rewards program, and Symphony’s higher-yield approach. Plus, the welcome off...

#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&nbs...

#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...

#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&nbs...

#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 Eleven...

#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 Ligh...

#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 docum...

#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 Buil...

#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 y...

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 d...

#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 nea...

#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 pod...

#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 h...

#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...

#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/hid...

#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 evacuati...

#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-kry...

#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/...

#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 wha...

#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 Institu...

#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...

#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...

#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 more. Link to Full Show Notes: https://chrishutchins.com/50k-points-japan-trip Partner Deals Upwork: ⁠Free job posting to find, hire, and pay top freelance talent...