Podcast
April 1, 2026
My Process for Booking Travel with Points & Miles
#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. ...
March 25, 2026
How to Actually Live the Life You're Optimizing For with Sahil Bloom
#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, an...
March 18, 2026
Ski Trip Mishaps, AI Interior Design, Reflecting on Life and More
#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. Partner Deals NetSuite: Free KPI check...
March 11, 2026
Navigating Transfer Bonuses, Hyatt Devaluation, New Card Offers and More
#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 usi...
March 4, 2026
Stop Planning, Start Experimenting: A Science-Backed Approach to a Better Life with Anne-Laure Le Cunff
#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 les...
Feb. 25, 2026
Credit Cards: What's in My Wallet for 2026
#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...
Feb. 18, 2026
Why Change Is Hard and How to Make It Your Advantage with Maya Shankar
#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 t...
Feb. 11, 2026
I Built an AI Assistant That Works While I Sleep
#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 bef...
Feb. 4, 2026
Deep Dive on Bilt Rewards and New Bilt 2.0 Cards
#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 strat...
Jan. 28, 2026
How to Earn Millions of Points and More Listener Q&A
#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 a...
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...