Podcast
Jan. 21, 2026
Points & Miles in 2026: What's New, What's Dying & What's Next with Brian M
#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...
Jan. 14, 2026
Goals, Tools, and Mindset Shifts for a Better 2026 with Kevin Rose
#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 optimi...
Jan. 7, 2026
Top 10 Takeaways from 2025
#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. Partner Deals Gusto: Free 3-mon...
Dec. 31, 2025
Choosing the Problems Worth Struggling For with Mark Manson
#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, an...
Dec. 17, 2025
My Top 5 Mistakes with Points & Miles
#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. ...
Dec. 10, 2025
End of Year Checklist for Your Taxes, Points and Miles
#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-im...
Dec. 3, 2025
The Easy Way to Build and Maintain Meaningful Relationships with Nick Gray
#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 ...
Nov. 19, 2025
2025 Holiday Gift Guide and Ways to Save This Season
#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, ...
Nov. 12, 2025
The Cost of Always Optimizing with Chris and Amy
#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. Partner Deals NetS...
Nov. 5, 2025
10 Lessons That Challenged My Thinking on Money and Life
#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 ...
Oct. 29, 2025
Family Travel on Points: Tips, Tricks and Tactics with Nick Reyes
#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 wi...
Oct. 22, 2025
How to Focus on What Matters and Let Go of the Rest with Ryan Holiday
#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-di...
Oct. 15, 2025
Open Enrollment, Diversifying Investments, Buying Gold and More Listener Q&A
#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. Partner Deals Fabric: Affordable term life insurance fo...
Oct. 8, 2025
Earn More Points in Multiplayer Mode with Kai
#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 ...
Oct. 1, 2025
How to Stop Over-Optimizing and Focus on What Matters with Tim Ferriss
#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 beh...
Sept. 24, 2025
Deep Dive on Bank of America Credit Cards (Up to 5.25% Cash Back)
#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...
Sept. 17, 2025
Contrarian Takes on Money, Risk, and Retirement with Tyler Gardner
#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 purpo...
Sept. 10, 2025
How Much Are Points and Miles Worth in 2025?
#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 sm...
Sept. 3, 2025
How I Saved $10,000+ on Luxury Hotels
#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, h...
Aug. 27, 2025
Smarter Strategies for Retirement, Wealth Building, and Taxes with Michael Kitces
#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) dis...
Aug. 20, 2025
Deep Dive on Capital One Credit Cards and Miles (+ Why I Love Them)
#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, impor...
Aug. 13, 2025
Earn More Points with New Cards, Bonuses, and Challenges in 2025
#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. Partner De...
Aug. 6, 2025
Top Airline & Hotel Transfer Partners to Maximize Your Points with Greg the Frequent Miler
#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 ...
July 30, 2025
Mini Retirements: How to Take a Break Sooner That Could Also Boost Your Career and Income with Jillian Johnsrud
#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 pitf...
July 23, 2025
18 Tactics for Booking Travel with Points & Miles
#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...