All the Hacks: Money, Points & Life

#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...

#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...

#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://chrishu...

#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 t...

#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...

#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...

#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 personaliz...

#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...

#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 auth...

#267: Chris reviews his credit card lineup for 2026, sharing which cards he's keeping and canceling and why. He also covers how to evaluate annual fees, the best cards across major spending categories, and the apps he uses to stay on top of it all. Link to Full Show Notes: https://chrishutchins.com/whats-in-my-wallet-2026/ Link to Cards Mentioned: https://chrishutchins.com/blog/whats-in-my-wallet-...

#266: Chris and Maya break down the science-backed tools that make change easier and more intentional. They explore why most people misunderstand change, how to anchor your identity to your deeper “why,” and practical tools to break out of rumination and navigate uncertainty. Maya Shankar is the bestselling author of The Other Side of Change, and hosts the podcast A Slight Change of Plans. She pre...

#265: Chris explores how modern AI tools have eliminated the barriers to building software, why planning matters more than coding skill, how anyone can turn a simple problem into a working app faster and cheaper than ever before, and how he built a personal AI assistant that's already started to run his life behind the scenes. Link to Full Show Notes: https://chrishutchins.com/how-to-build-with-ai...

#264: Learn how the Bilt ecosystem works, from earning Bilt Rewards to the new cards, transfer partners, perks, and where the real value is. Whether you’re new or already earning, this is a practical guide to using Bilt strategically and avoiding common mistakes. Link to Full Show Notes: https://chrishutchins.com/bilt-ecosystem-explained Partner Deals DeleteMe: 20% off removing your personal info...

#263: Chris breaks down exactly how he’s earned millions of points and miles, and why simplicity matters more than optimization. He covers signup bonuses, spending strategies, credit score impacts, business cards, cash-back alternatives, and how to decide when a card (or perk) is actually worth it. Link to Full Show Notes: https://chrishutchins.com/points-and-miles-simplified-credit-cards Partner...

#262: Learn how to navigate major changes in points and miles while maximizing travel rewards in 2026. Chris and Brian M cover Bilt 2.0, the Mesa card shutdown, how to evaluate annual fees, find award availability, and what’s likely (and unlikely) to change this year. Link to Full Show Notes: https://chrishutchins.com/latest-on-points-miles-january-2026 Partner Deals Trust & Will: Get 20% off pers...