All the Hacks: Money, Points & Life

#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+ fou...

#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...

#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 Breakthro...

#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 Del...

#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-fina...

#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-...

#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 Delet...

#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 famil...

#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...

#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 Frequ...

#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...

#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 Gu...

#249: 3x your points and miles with a multiplayer strategy. We break down how to earn, manage, and maximize rewards with a partner, family, or friends. Plus learn how to handle the logistics, emotions, and systems that make it all work. Kai is the founder and host of The Daily Churn Podcast, where he shares his churning journey. In 2024, Kai and his partner earned a total of $40,000 and 5 million...

#248: Learn to escape the trap of over-optimizing and design a more meaningful life. We explore setting boundaries, resetting priorities, and turning failure into fuel for success. We also dive into Tim’s creative process behind his new card game and the surprising value of play. Tim Ferriss is an entrepreneur, bestselling author, and host of The Tim Ferriss Show, one of the world’s most popular p...

#247: Chris dives into Bank of America’s credit card lineup and why he has 5 different BoA cards right now. He'll go over how the Preferred Rewards program can help you earn unlimited 3.3% back on everything. Finally, he also covers approval rules, credit limits, unique perks like free museum access, and more. Link to Full Show Notes: https://chrishutchins.com/bank-of-america-preferred-rewards Par...

#246: Today we explore contrarian takes on budgeting, the 4% rule, retirement planning, and the risks of blindly investing in bonds. We also cover strategies for investing, spending, and rethinking how to use money with purpose. Tyler Gardner is a personal finance creator, educator, and former portfolio manager who’s built a following by challenging conventional money wisdom. He's also the host of...

#245: Ever wonder what points are really worth? I'll break down the different types of points, how to calculate their value, and the biggest mistakes people make along the way. You’ll also learn when cash back might be the smarter choice and my personal card strategy for maximizing credit card rewards. Link to Full Show Notes: https://chrishutchins.com/what-are-your-points-worth Partner Deals Gelt...

#244: I'll explain how I saved over $10k on luxury hotels in Costa Rica and Carmel Valley using points, free nights, and elite perks. I’ll walk you through every step, from how to book with points, when to buy them on sale, how to stack hotel credits, which hotel programs give you upgrades and free breakfast, and more! Link to Full Show Notes: https://chrishutchins.com/maximize-savings-costa-rica-...

#243: Discover smarter strategies to grow your wealth and create financial flexibility. We dive into when it makes sense to invest beyond retirement accounts, how to access savings early through Roth conversions and 72(t) distributions, ways to reduce taxes with HSAs, tax-advantaged accounts, and charity, and so much more. Michael Kitces is the Head of Planning Strategy at Focus Partners Wealth, c...

#242: Chris dives into the Capital One credit card lineup, breaking down earning structures for miles and cash back, exciting benefits, and redemption strategies. He also covers the best 2-card combo, transfer partners, important application rules, and more. Link to Full Show Notes: https://chrishutchins.com/capital-one-credit-cards-miles-guide Partner Deals Superhuman: Free month of the fastest a...

#241: We cover new credit cards, increased welcome bonuses, and major changes to existing cards and their benefits. Plus, learn how to rack up thousands of points through airline and hotel challenges and giveaways. Link to Full Show Notes: https://chrishutchins.com/new-cards-increased-offers-points-challenges Partner Deals Copilot Money: Free 2 months access to my favorite personal finance app wit...

#240: Transferring points is one of the best ways to maximize your points, so today we share the top airline and hotel transfer partners. We also cover strategies to get the most out of your points, including how to leverage transfer bonuses, identify sweet spots, avoid common mistakes, and more. Greg Davis-Kean is the founder of Frequent Miler, a blog dedicated to helping people maximize their tr...

#239: Why wait until you're 65? It's feasible for almost anyone to take a mini retirement and when done right, it can also fast-track your career and income. Learn how to plan one, negotiate time off, manage costs, avoid pitfalls, and make it work if you’re self-employed. Plus, we share tips for handling health insurance and other logistics during your mini-retirement. Jillian Johnsrud is the auth...

#238: Chris shares 18 tactics he’s used to get the best deals booking flights and hotels with points. Learn how to leverage flexibility, navigate transfer partners, use the right tools, identify “sweet spots,” avoid high fees, position flights, and so much more. Link to Full Show Notes: https://chrishutchins.com/18-tactics-for-booking-award-travel Partner Deals MasterClass: Learn from the world's...

#237: Start living your rich life today regardless of your income. Learn how to spend without guilt, track the four key financial numbers that matter most, harness the power of decisiveness, and avoid the common traps that hold people back as their income grows. Ramit Sethi is a personal finance expert and the NYT bestselling author of I Will Teach You to Be Rich. He hosts the popular Netflix show...