Podcast
June 10, 2026
Saving Money and Optimizing is My Kryptonite
#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...
June 3, 2026
Taking My Health Into My Own Hands: Tests, Records, and What Actually Worked
#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, ho...
May 27, 2026
The Hidden Rules of Credit Card Approvals
#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 les...
May 20, 2026
How Long-Term Investors Actually Think About Risk with Ben Carlson
#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 psychological...
May 13, 2026
The AI Tools I'm Building to Replace My Spreadsheets with Anish Acharya
#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 re...
May 6, 2026
The Japan ER Visit That Changed How We Travel (& Tokyo Disney) with Amy Fox
#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 t...
April 29, 2026
Saving $30K+ on the Perfect Spring Break Japan Trip with Amy Fox
#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 ...
April 22, 2026
The Custom Everything Era with Kevin Rose
#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 th...
April 15, 2026
The Surprising History of Points and Miles
#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 wi...
April 8, 2026
Stop Overthinking and Start Deciding with Derek Sivers
#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 actua...
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. ...