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

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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.
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#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

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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.
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#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

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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.
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#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/

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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.
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#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