All the Hacks: Money, Points & Life

#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 this means for jobs, creativity, and human connection.

Kevin Rose is the host of Diggnation and a partner at True Ventures, an early-stage venture capital firm that has invested over $4 billion in a portfolio of over 400+ founders. Kevin previously founded Zero and Oak, and was a partner at Google Ventures.

Link to Full Show Notes: https://chrishutchins.com/using-ai-tools-today-kevin-rose

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

Resources Mentioned

Kevin Rose: Diggnation | Newsletter

AI Tools & Platforms


Claude


OpenClaw


ChatGPT


Google Gemini


ElevenLabs


Vercel

Japan Travel


Craig Mod's Blog


Park Hyatt Tokyo


KidZania Tokyo

Articles & Pop Culture


Leica and Content Authenticity Initiative


All-In Podcast episode with Travis Kalanick


The Pitt


Joker Greeting

ATH Podcast


Newsletter


Gift Card Site


Leave a review: Apple Podcasts | Spotify


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

Full Show Notes

(00:00) Introduction

(01:07) Are We Actually Saving Time with AI—or Just Wasting It Faster?

(10:03) The Real Risks of Sharing Your Data with AI Tools

(21:18) Why It’s Never Been Easier to Build and Create

(28:12) Has AI Content Already Gone Too Far?

(37:37) How AI Is Reshaping Human Interaction

(40:43) The Growing Need to Verify What’s Real

(46:33) Investing in a World Being Disrupted by AI

(51:44) Where Jobs Are Headed in the AI Era

(55:02) What Happens to Art When Anyone Can Create?

(56:47) Tips for Planning a Trip to Japan

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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#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 wildly profitable, why loyalty programs are worth more than the airlines, the psychology behind why you keep hoarding points, and more. 

Link to Full Show Notes: https://chrishutchins.com/history-of-points-and-miles

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

Resources Mentioned

Movie:  The Man From The Diners Club

Book: Mileage Maniac by Steve Belkin

Video: How Airlines Quietly Became Banks

Articles


Credit-card cash reshapes US airline loyalty — and profit by Reuters


Interview with Matty Simmons by The Saturday Evening Post


Who Pays For Your Rewards? Redistribution in the Credit Card Market by Agarwal, Presbitero, Silva, and Wix

ATH Podcast


Best Cards Page


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

(00:53) The Very Beginning of Points & Miles

(04:07) How Credit Cards Came to Exist

(08:24) The Legal Accident that Made Credit Cards Profitable

(15:50) The History of Rewards

(19:06) The Story of Air Pass

(23:20) The First Airline Co-branded Credit Cards

(25:21) How the Credit Card System Works Between Different Banks

(29:38) How the Airline Rewards System Works

(35:32) Airline Rewards Grade Devaluations

(37:31) Examples of Rare Airline Reward Point Opportunities

(39:33) The Endowed Progress Effect

(40:38) The Goal Gradient Effect and Chasing Airline Rewards

(41:09) The Sunk Cost Fallacy

(41:47) The Separate Mental Accounts Effect

(42:46) Quick Summary of the History of Miles & Points

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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#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

ATH Podcast


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

(02:39) 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

⁠⁠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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#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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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

⁠⁠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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#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.
Learn more about your ad choices. Visit megaphone.fm/adchoices