All the Hacks: Money, Points & Life

#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 actually want, and more.

Derek Sivers is an entrepreneur, writer, and self-proclaimed "slow thinker" best known for founding CD Baby, which he sold for $22M and gave the proceeds to charity. He’s since dedicated his life to creating, learning, and writing books like Hell Yeah or No.

Link to Full Show Notes: https://chrishutchins.com/derek-sivers-stop-overthinking-make-better-decisions

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For all the deals, discounts and promo codes from our partners, go to: ⁠chrishutchins.com/deals

Resources Mentioned

Derek Sivers: Website | X


Book: Hell Yeah or No: what's worth doing


Articles: My Heroes | Actions, Not Words, Reveal Our Real Values | Parenting: Who Is It Really For? | Travel Is Best With Young Children | Relax for the Same Result | How To Ask Your Mentors For Help

Books Mentioned: The Paradox of Choice | Brain Rules for Baby

New Zealand Recommendation: Staglands Wildlife Reserve

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Email for questions, hacks, deals, and feedback: [email protected]

Full Show Notes

(00:00) Introduction

(02:39) Turning Intentions Into Reality

(07:34) Reflecting On What You Want And Why

(13:39) Methods For Decision-Making

(16:23) Learning To Pause, Reflect, And Push Back Through Journaling

(31:01) Making Decisions When There Are Too Many Options

(37:15) Coin Toss: Noticing Your Feelings While The Coin Is In The Air

(39:52) Paradox Of Choice: Satisfice Not Maximize

(50:30) Theory Vs. Practice

(58:53) Decision-Making Based On Personal Goals And Aspirations

(01:03:14) Actions Reveal Values

(01:08:30) The Power of Saying No

(01:18:18) Parenting Perspective

(01:22:31) Traveling With Children

(01:31:53) Adjusting Expectations

(01:41:07) Relax for The Same Result

(01:49:42) Derek Sivers’ New Zealand Recommendations

Connect with Chris

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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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#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. transfers, plus the mindset shifts that make the whole process work.

Link to Full Show Notes: https://chrishutchins.com/booking-travel-with-points-and-miles-2026

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Bilt Rewards: ⁠Earn the most valuable points when you pay rent

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For all the deals, discounts and promo codes from our partners, go to: ⁠chrishutchins.com/deals

Resources Mentioned

Award Search Tools


AwardTool ($20 off annual plans with code ALLTHEHACKS)


point.me (20% off annual plans with code ALLTHEHACKS20)


PointsYeah


Seats.Aero


Points Path Browser Extension


FlightConnections

Credit Cards


Best Cards Page


CardTool App


Marriott Bonvoy Brilliant® American Express® Card

ATH Podcast


Ep 166: Best Award Search Tools for Booking Flights with Points & Miles with Greg the Frequent Miler


Ep 227: The Path to Becoming an Expert in Points & Miles with Devon Gimbel


Ep 238: 18 Tactics for Booking Travel with Points & Miles


Ep 244: How I Saved $10,000+ on Luxury Hotels


Ep 258: My Top 5 Mistakes with Points & Miles


Membership


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

(01:10) Two Ways to Use Points for Travel

(06:30) Define Your Flexibility Before You Search

(11:42) Clarify What You Actually Want From A Trip

(15:00) When to Start Planning (and Why Earlier Is Almost Always Better)

(18:48) How To Find Award Availability

(19:55) The Best Award Search Tools & How to Use Them

(21:17) How Award Tools Work

(23:30) Using Alerts To Find Better Flights

(26:15) What To Do When You Can’t Find Availability

(28:31) How to Book for a Group When Availability Is Tight

(31:32) Why You Should Book One-Way Flights

(32:27) How To Use Points For Domestic Flights

(34:38) The Best Tool For Domestic Award Searches

(35:05) Why Diversifying Your Points Unlocks More Domestic Options

(36:36) Should You Ever Use Points to Upgrade Seats?

(39:00) Are Travel Portals Worth It?

(39:36) The Case Against Using Travel Portals

(42:09) The Case For Using Travel Portals

(45:17) How To Think About Chase Points Boost

(48:26) When Using Points For Hotels Makes Sense

(50:50) The Best Ways to Earn Hotel Points

(53:54) The Award Booking Index Card

Connect with Chris

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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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#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

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