All the Hacks: Money, Points & Life

#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 Full Show Notes: https://chrishutchins.com/sahil-bloom-stop-over-optimizing-life Partner Deals Quince: Affordable luxury essentials with free shipping + 365 day returns Mercury: ⁠Manage, move, and grow your money LMNT: ⁠Free sample pack of my favorite electrolyte drink mix Fabric: ⁠Affordable term life insurance for you and your family MasterClass: ⁠Learn from the world's best with 15% off For all the deals, discounts and promo codes from our partners, go to: ⁠chrishutchins.com/deals Resources Mentioned Sahil: Website | Newsletter | X Wild Roman: 10% off with code CHUTCHINS10 Books & Articles The 5 Types of Wealth by Sahil Bloom A Reflection On The Little Things The Doorman Fallacy The Real AI Risk Nobody Told You About The 2028 Global Intelligence Crisis Rule for Life: Don't Complain AI Tools Deep Personality Lemon Wispr Flow Phone Lock Box: Mindsight Timed Lock Box Full Show Notes (00:00) Introduction (00:58) Why Sahil Moved His Entire Family from New York to Boston (03:09) Why Big Life Changes Should Happen Fast (04:47) The Real ROI of Small Moments (06:27) The Doorman Fallacy: What You Lose When You Optimize the Surface (10:32) Designing Your Life vs Letting It Happen (15:15) The Tradeoffs of Living Near Opportunity (22:17) Why Now Is the Best Time in History to Be Curious (30:05) How Sahil Actually Uses AI Day-to-Day (36:23) Solomon's Paradox: Why We Can't Take Our Own Advice (38:45) Using Voice Agents to Think Better (40:03) Balancing Work, Family, and Time (45:47) Why Motivation Is Overrated and Choice Architecture Wins (49:11) Making Workouts Non-Negotiable Without Sacrificing Work (52:54) How Often to Audit Your Routines (Before They Start Owning You) (53:42) Why Sahil Invested $1M of His Own Money in a Skincare Company Connect with Chris ⁠⁠Newsletter⁠⁠ | ⁠Membership⁠⁠ | ⁠X⁠⁠ | ⁠Instagram⁠⁠ | ⁠LinkedIn⁠⁠ Editor’s Note: The content on this page is accurate as of the posting date; however, some of our partner offers may have expired. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. Learn more about your ad choices. Visit megaphone.fm/adchoices

#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 estate plans DeleteMe: 20% off removing your personal info from the web Upwork: Free job posting to find, hire, and pay top freelance talent For all deals, discounts, and promo codes from our partners, visit:chrishutchins.com/deals Resources Mentioned Delta SkyMiles® Reserve American Express Card Ski & Travel Epic Pass Woodward Vrbo Kirkwood Etekcity Luggage Scale AI Tools Gemini Claude ChatGPT Nano Banana Google Sites Bee Limitless Pendant Wispr Flow Deep Personality Home Gadgets Skylight Aura Frames Paprika Ratio Eight Series 2 Baratza Forté™ BG Health & Wearables Oura Ring WHOOP (← 1 month free) One Medical Blueberry Pediatrics (← $100) Money & Finance Mercury Copilot Money (free 2 months access with code HACKS2) ATH Podcast Ask Chris Anything! Newsletter #237: ⁠How to Design a Rich Life at Any Income with Ramit Sethi #268: Stop Planning, Start Experimenting: A Science-Backed Approach to a Better Life with Anne-Laure Le Cunff Leave a review: Apple Podcasts | Spotify Email for questions, hacks, deals, and feedback: [email protected] Full Show Notes (00:00) Introduction (00:55) The Lost Clothes Disaster and A Surprisingly Good Outcome (14:30) What Ski Trips Are Really Like With Kids (15:06) This Ski Season vs. Last Ski Season (18:14) Smarter Ways To Book Houses for Ski Travel (19:03) How To Save Money on Checked Bags for Ski Trips (19:37) A Shoutout to the New Delta Sky Club in Terminal 2 (20:07) When It’s Better To Drive Instead of Fly (21:42) How Amy Has Been Redesigning Rooms in the House (23:22) Why AI Is Such a Powerful Tool for Home Design (23:54) Amy’s Step-by-Step Process for Redesigning a Room With AI (25:02) The AI Tools Amy Used and What Each One Did Best (29:51) Using AI To Find Better Furniture Ideas (32:38) How Much Money AI Saved vs. Hiring a Designer (34:18) New House Gadget: The Skylight Calendar (36:25) Why We Love the Ratio Coffee Machine Gen 2 and the Baratza Grinder (39:50) Oura Ring vs. WHOOP Band (42:53) Bee, Wearable AI, and the Future of Personal Memory (50:30) What It Looks Like To Integrate AI Deeply Into Daily Life (54:22) What We Learned Switching to a High-Deductible Health Plan (01:03:11) Best Practices for Combining Finances as a Couple Connect with Chris ⁠Newsletter⁠ | ⁠Membership⁠ | ⁠X⁠ | ⁠Instagram⁠ | ⁠LinkedIn⁠ Editor’s Note: The content on this page is accurate as of the posting date; however, some of our partner offers may have expired. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. Learn more about your ad choices. Visit megaphone.fm/adchoices

#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 insurance for you and your family Gusto: Free 3-month trial of the #1 payroll software Mercury: Manage, move, and grow your money Bilt Rewards: Earn the most valuable points when you pay rent For all the deals, discounts and promo codes from our partners, go to: chrishutchins.com/deals Resources Mentioned AI Models & Assistants ChatGPT OpenClaw Gemini Claude | Claude Cowork Oura Ring OpenSnow Gridfinity JAL USA CARD Rove Miles Transfer Bonuses in March 2026 Citi → Wyndham: 25% bonus (ends 3/21) Amex → Avianca LifeMiles: 15% bonus (ends 3/28) Rove Miles → Japan Airlines: 50% bonus (ends 3/31) Capital One → Preferred Hotels: 30% bonus (ends 3/31) Massive Hyatt Points Devaluation Credit Cards Best Cards Page Robinhood Gold Card U.S. Bank Smartly™ Visa Bilt Palladium Card (Rates and fees here) Delta SkyMiles® Gold Business American Express Card Delta SkyMiles® Platinum Business American Express Card Delta SkyMiles® Reserve Business American Express Card Hilton Honors American Express Card Hilton Honors American Express Surpass® Card The Hilton Honors American Express Business Card Hilton Honors American Express Aspire Card The Platinum Card® from American Express American Express® Business Gold Card The Business Platinum Card® from American Express WHOOP (1 month free here) Function Health ATH Podcast Ask Chris Anything! Newsletter Ep #265: I Built an AI Assistant That Works While I Sleep Ep #264: Deep Dive on Bilt Rewards and New Bilt 2.0 Cards Leave a review: Apple Podcasts | Spotify Email for questions, hacks, deals, and feedback: [email protected] Full Show Notes (00:00) Introduction (00:55) Chris's New AI Agent (04:00) How To Leverage Claude Cowork  (06:14) How Chris Used AI to Build a New CardTool (08:52) The Future of The Internet  (17:21) 3D Printing (18:39) Taking Advantage of Transfer Bonuses (21:56) Bilt Rent Day Transfer Bonuses (27:09) Rove Transfer Bonus to JAL & Other Bonuses (33:22) Hyatt's Massive Devaluation (38:54) How to Get More Points with Potential Devaluations (41:15) Welcome Offers on Delta Cards (45:12) Welcome Offers on United Cards (48:28) Welcome Offers on Hilton Cards (51:13) Welcome Offers on Southwest Cards (53:30) Cards with Big-Point Offers  (54:13) Find the Latest Deals on the ATH Newsletter  (54:45) Card-Linked Deals for Whoop and Function Health Connect with Chris Newsletter | Membership | X | Instagram | LinkedIn Editor’s Note: The content on this page is accurate as of the posting date; however, some of our partner offers may have expired. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. Learn more about your ad choices. Visit megaphone.fm/adchoices

#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 growth. Link to Full Show Notes: https://chrishutchins.com/tiny-experiments-anne-laure-le-cunff/ Partner Deals Shopify: $1/month trial for the easiest e-commerce platform DeleteMe: 20% off removing your personal info from the web Gelt: Skip the waitlist on personalized tax guidance to maximize your wealth Green Chef: 50% off on your first box + 20% off for two months with code 50ALLTHEHACKS Superhuman: Free month of the fastest and best email with code ALLTHEHACKS For all the deals, discounts and promo codes from our partners, go to: ⁠chrishutchins.com/deals⁠ Resources Mentioned Anne-Laure: Website | Newsletter | Instagram Tiny Experiments Ness Labs ATH Podcast Ep #256: The Easy Way to Build and Maintain Meaningful Relationships with Nick Gray Leave a review: Apple Podcasts | Spotify Email for questions, hacks, deals, and feedback: [email protected] Full Show Notes (00:00) Introduction (01:01) The Problem with Setting Big Goals (02:42) When Goal Setting Becomes Counterproductive (03:41) Why Tiny Experiments Beat Goals (06:07) The Missing Ingredients That Make Experiments Actually Work (08:29) How an Experimental Mindset Rewires Your Brain (10:11) How Anne-Laure Adopted an Experimental Mindset (13:38) What Happened When Anne-Laure Redefined Success (16:29) How to Run a Tiny Experiment (18:22) Real-World Examples You Can Try Immediately (20:10) Why Smaller Is Always Better When Starting Out (22:28) How to Experiment Without Burning Out (25:05) Tracking Both External Results and Internal Signals (30:10) The Simple Weekly Review That Keeps Experiments on Track (32:18) Balancing Experimentation With Actually Living Your Life (35:45) Applying Experimentation to Financial Security (39:33) The Real Reason We Over-Optimize (42:15) When Optimizing Is Actually the Right Move (46:09) Balancing Excitement With Long-Term Priorities (50:12) Measuring Time Differently (52:20) Simple Rituals for Getting Present (53:25) Why Experimenting Publicly Accelerates Growth (57:26) How to Run Your Very First Experiment (59:26) Where to Find Anne-Laure and Her Work Connect with Chris ⁠Newsletter⁠ | ⁠Membership⁠ | ⁠X⁠ | ⁠Instagram⁠ | ⁠LinkedIn⁠ Editor’s Note: The content on this page is accurate as of the posting date; however, some of our partner offers may have expired. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. Learn more about your ad choices. Visit megaphone.fm/adchoices

#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 effortless voice dictation for free Mercury: Manage, move, and grow your money Gelt: Skip the waitlist on personalized tax guidance to maximize your wealth LMNT: Free sample pack of my favorite electrolyte drink mix For all the deals, discounts and promo codes from our partners, go to: chrishutchins.com/deals Resources Mentioned CardTool App (Free access here) ⁠Credit Card Holder Wallet⁠ 1Password Blog Posts Premium Card Worksheet How to maximize your Hilton cards 6 reasons to avoid booking through an online travel agency Existing Bank of America relationship customers to keep status longer Credit Card Trackers CardPointers Pro (30% off here and 50% off here) CardRight Travel Freely ATH Podcast Best Cards Page CardTool App Membership Chris’s Card Optimization Spreadsheet AMA: Submit A Question Leave a review: Apple Podcasts | Spotify Email for questions, hacks, deals, and feedback: [email protected] Full Show Notes (00:00) Introduction (02:42) 3 Key Reasons to Get A Credit Card (05:23) Chris' Credit Card Goals for 2026 (08:31) Evaluating The Net Annual Fee of A Card (12:56) The Amex Card Stack (23:19) Co-Branded Marriott Cards (25:32) Co-Branded Hilton Cards (27:00) Co-Branded Delta Cards (28:12) The Amex Blue Card (30:34) A Popular Bank's Cards (33:10) World of Hyatt Business Card (33:30) Co-Branded Southwest & United Cards (40:41) More Cards From The Popular Bank (42:11) Capital One Venture Cards (45:17) Bank of America Card Stack (51:09) Alaska Atmos Cards (53:24) US Bank Cards (55:22) Citi Bank Cards (56:56) Wells Fargo Autograph Card (57:43) The Bilt Palladium Card (59:25) Assessing The Major Spending Categories (01:06:32) Cards for Amazon & Costco (01:07:13) The Best "Everything Else" Card (01:08:47) Chris's Takeaway on Credit Card Spending Categories (01:09:26) The Best Card Combos (01:13:00) Credit Card Trackers Connect with Chris Newsletter | Membership | X | Instagram | LinkedIn Editor’s Note: The content on this page is accurate as of the posting date; however, some of our partner offers may have expired. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. Learn more about your ad choices. Visit megaphone.fm/adchoices