Upgrade your life, money and travel.
#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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Resources Mentioned
Kevin Rose: Diggnation | Newsletter
AI Tools & Platforms
Japan Travel
Articles & Pop Culture
ATH Podcast
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
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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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#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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DeleteMe: 20% off removing your personal info from the web
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
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
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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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#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
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
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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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Gelt: Skip the waitlist on personalized tax guidance to maximize your wealth
Bilt Rewards: Earn the most valuable points when you pay rent
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Green Chef: 50% off your first month + 20% off for two months with code 50ALLTHEHACKS
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)
Credit Cards
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
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
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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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Resources Mentioned
Sahil: Website | Newsletter | X
Wild Roman: 10% off with code CHUTCHINS10
Books & Articles
AI Tools
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
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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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#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:
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Resources Mentioned
Ski & Travel
AI Tools
Home Gadgets
Health & Wearables
Money & Finance
ATH Podcast
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
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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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#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
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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
Transfer Bonuses in March 2026
Massive Hyatt Points Devaluation
Credit Cards
ATH Podcast
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
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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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#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
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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
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
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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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#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/
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Mercury: Manage, move, and grow your money
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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)
Blog Posts
Credit Card Trackers
ATH Podcast
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
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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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#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 to break out of rumination and navigate uncertainty.
Maya Shankar is the bestselling author of The Other Side of Change, and hosts the podcast A Slight Change of Plans. She previously served as a Senior Advisor in the Obama White House, where she founded and led the White House Behavioral Science Team.
Link to Full Show Notes: https://chrishutchins.com/navigating-change-maya-shankar
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DeleteMe: 20% off removing your personal info from the web
Fabric: Affordable term life insurance for you and your family
For all the deals, discounts and promo codes from our partners, go to: chrishutchins.com/deals
Resources Mentioned
Quit: The Power of Knowing When to Walk Away by Annie Duke
ATH Podcast
Full Show Notes
(00:00) Introduction
(00:38) What People Get Wrong About Change
(05:14) The Antidote That Makes Change Easier
(12:11) Past Change vs. Intentional Change
(16:02) Maximisers vs. Satisficers
(19:10) Anchor Your Identity to Your Why
(23:15) How to Discover Your Why
(25:03) Navigating Change With a Very Different Partner
(29:17) Breaking the Rumination Cycle
(29:58) Mental Time Travel
(31:55) Affect Labeling
(32:39) Tools for Better Self-Understanding
(36:01) AI as a Conversational Partner
(39:43) Tactics For Thinking Through Big Changes
(42:01) Moral Elevation
(43:36) Why Reading Fiction Matters
(44:29) Repurposing Your Experience
(45:34) The First Step When Everything Changes
(47:31) Where to Find More From Maya
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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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#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 before, and how he built a personal AI assistant that's already started to run his life behind the scenes.
Link to Full Show Notes: https://chrishutchins.com/how-to-build-with-ai-tools
Partner Deals
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Mercury: Help your business grow with simplified finances
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
For all the deals, discounts and promo codes from our partners, go to: chrishutchins.com/deals
Resources Mentioned
AI Models & Assistants
AI Coding & Building Tools
Productivity & Automation Tools
Developer Infrastructure
FinTech: Plaid
How to Run OpenClaw as your Virtual EA
Blogs
Credit Cards
ATH Podcast
Full Show Notes
(00:00) Introduction
(01:41) Why This Is the Best Time Ever to Build Software
(04:14) How to Build Almost Anything with AI
(13:53) Why Context Is the Real Superpower
(15:58) Using Planning Mode Instead of Guessing
(16:41) Which AI Tool Should You Start With?
(17:53) Building a Real Credit Card Optimizer from Scratch
(28:48) What It Actually Costs to Build with AI
(32:38) The Real AI Learning Curve
(33:38) Moving from Cursor to Claude Code
(36:17) Why You Should Try Building Something (Even If You're Not a Coder)
(37:00) How OpenClaw Changes the Game
(38:57) Why Security Still Matters
(42:25) A Conversation with Ted, Chris' AI Assistant
(44:07) Letting AI Work While You Sleep
(49:41) Learning to Be Clear, Specific, and Intentional
(50:03) Start with a Real Problem
(50:39) Breaking Projects into Small, Winnable Pieces
(50:58) What Would You Build If Building Were Easy?
(51:59) Keeping Track of Cost and Budget
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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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