Podcast

#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: 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: 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: 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: 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...

#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...

#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-for-2026/ Partner Deals MasterClass: Learn from the world's best with 15% off Wispr Flow: Try eff...

#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 previously served as a Senior Advisor in the Obama White House, where she founded and led the White Ho...

#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-tools Partner Deals Green Chef: 50% off on your first box + 20% off for two months with code 50AL...

#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 from the web Copilot Money: Free 2 months access to my favorite personal finance app with code HAC...

#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 Deals Fabric: Affordable term life insurance for you and your family Bilt Rewards: Earn the most v...

#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 personalized, legally binding estate plans MasterClass: Learn from the world's best with 15% off Thriv...

#261: Chris and Kevin reflect on 2025’s biggest wins and lessons, then dive into how they're planning 2026. They share their goals, the tools they're using, and why they're designing a year that’s easier, not just more optimized. 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 was a partner at Google Ventures. Link to Full S...

#260: Chris distills the most powerful lessons from over 50 episodes in 2025 into 10 actionable takeaways that changed how he thinks about money, time, health, relationships, purpose, and more. Link to Full Show Notes: https://chrishutchins.com/top-takeaways-2025-optimize-money-travel-life Partner Deals Gusto: Free 3-month trial of the #1 payroll software Notion: Try Notion Agent free to automate tedious tasks and streamline your work Superhuman: Free month of the fastest and best email with c...

#259: Learn how to pick the challenges in life that actually matter. We break down how to stop optimizing for the wrong things, why values trump goals in decision-making, practical strategies for building real friendships, and more. Mark Manson is the bestselling author of The Subtle Art of Not Giving a F*ck (20M+ copies sold). He hosts the Solved podcast, writes the newsletter Your Next Breakthrough, and co-founded Purpose, an AI tool for exploring purpose and values. Link to Full Show Notes:...

#258: The 5 biggest mistakes Chris has made in his points & miles journey. He dives into the hidden cost of status, the math behind point values, the power of opportunity cost, and why hoarding points quietly destroys value. Link to Full Show Notes: https://chrishutchins.com/top-5-points-and-miles-mistakes Partner Deals Superhuman: Free month of the fastest and best email with code ALLTHEHACKS DeleteMe: 20% off removing your personal info from the web LMNT: Free sample pack of my favorite elec...

#257: We break down essential tax and financial decisions to make before year-end. Learn how to maximize deductions, optimize charitable giving, manage investment gains and losses, and take advantage of retirement and home-improvement credits. We also run through all the credit card, points and miles deadlines to hit before 12/31. Link to Full Show Notes: https://chrishutchins.com/end-of-year-financial-checklist-2025 Partner Deals Vuori: 20% off the most comfortable performance apparel I've ev...

#256: We break down the simplest, most effective ways to build stronger friendships and stay connected as an adult. Plus, learn how to build a personal website, host better events, send a friends newsletter, book a cruise on a budget, and so much more. Nick Gray is an entrepreneur and author who built and sold two successful companies, Flight Display Systems and Museum Hack. His YouTube and short-form videos have reached over 55 million views. Link to Full Show Notes: https://chrishutchins.com...

#255: Here are 100+ holiday gift ideas across tech, kitchen, home, clothing, fitness, kids, and games. I’ll also share tools and tactics to help you find deals and spend less this holiday season. For all the products, links, deals and more, check out the full 2025 Gift Guide here: https://chrishutchins.com/gifts Link to Full Show Notes: https://chrishutchins.com/gift-guide-2025 Partner Deals DeleteMe: 20% off removing your personal info from the web LMNT: Free sample pack of my favorite elect...

#254: Chris and Amy share a candid look at their life together as two optimizers. They discuss everything from family finances and teaching their kids about money to managing their health, work, and travel. Link to Full Show Notes: https://chrishutchins.com/ama-amy-marriage-parenting-health Partner Deals NetSuite: Free KPI checklist to upgrade your business performance Storyworth: Share your family stories in a custom book (+ $10 off) DeleteMe: 20% off removing your personal info from the web ...

#253: My top 10 takeaways from a retreat for high-net-worth investors, which will cover investing, managing risk, investing in your health, building meaningful relationships, parenting with purpose, and defining success in a way that goes far beyond money. Tad Fallows is the co-founder of Long Angle, a private community for investors with more than $2.2 million in assets. He previously co-founded iLab Solutions, a global leader in cloud-based lab management software, which was acquired by Agile...

#252: Chris and Nick share strategies to make family travel affordable and stress-free with points and miles. They cover how to find multiple award seats, book business class for families, and their best tips for traveling with kids, from managing jet lag and delays to finding family-friendly hotels, must-have travel gear, and more. Nick Reyes is a writer at Frequent Miler and co-host of the Frequent Miler On The Air podcast. He is an avid traveler who's been to 60+ countries and loves collecti...

#251: Discover why Stoicism matters more than ever and how to make it part of your daily life. We share practical ways to focus on what you can control, build resilience, and cultivate the four Stoic virtues: courage, self-discipline, justice, and wisdom. Ryan Holiday is a bestselling modern philosopher and author of The Daily Stoic, The Obstacle Is the Way, Ego Is the Enemy, and Stillness Is the Key. His books on Stoic virtues have sold over 10 million copies in 40+ languages. He’s also the fo...

#250: Chris dives into listener questions, covering open enrollment, investing, buying gold, life and auto insurance, RSUs, practical ways to leverage AI tools and more. Link to Full Show Notes: https://chrishutchins.com/open-enrollment-AMA-2025 Partner Deals Fabric: Affordable term life insurance for you and your family Superhuman: Free month of the fastest and best email with code ALLTHEHACKS Gusto: Free 3-month trial of the #1 payroll software DeleteMe: 20% off removing your personal info f...