#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

#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

Partner Deals

Thrive Market: 30% off your first order of organic groceries + a free $60 gift

Gusto: Free 3-month trial of the #1 payroll software

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

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

Maya: Website | Instagram

• Book: The Other Side of Change
• Podcast: A Slight Change of Plans

Quit: The Power of Knowing When to Walk Away by Annie Duke

Deep Personality Assessment

ATH Podcast

• Ep #81: Making Smarter Decisions and Knowing When to Walk Away with Annie Duke
• Ep #265: I Built an AI Assistant That Works While I Sleep
• Leave a review: Apple Podcasts | Spotify
• Email for questions, hacks, deals, and feedback: [email protected]

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

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

#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

Green Chef: 50% off on your first box + 20% off for two months with code 50ALLTHEHACKS

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

• ChatGPT
• OpenClaw
• Gemini
• Claude

AI Coding & Building Tools

• Replit
• Lovable
• Cursor
• Codex

Productivity & Automation Tools

• Wispr Flow
• Zapier
• Nimble Links
• Tampermonkey

Developer Infrastructure

• Clerk
• Supabase
• GitHub

FinTech: Plaid

How to Run OpenClaw as your Virtual EA

Blogs

• Doctor of Credit
• Frequent Miler
• The Points Guy

Deep Personality

Credit Cards

• American Express® Gold Card
• Citi Strata Elite℠ Card
• Citi Strata Premier℠ Card
• Bilt 2.0

ATH Podcast

• Ep #263: How to Earn Millions of Points and More Listener Q&A
• Chris’ Card Optimizer Tool
• Ask Chris Anything!
• Leave a review: Apple Podcasts | Spotify
• Email for questions, hacks, deals, and feedback: [email protected]

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

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

#264: Learn how the Bilt ecosystem works, from earning Bilt Rewards to the new cards, transfer partners, perks, and where the real value is. Whether you’re new or already earning, this is a practical guide to using Bilt strategically and avoiding common mistakes.

Link to Full Show Notes: https://chrishutchins.com/bilt-ecosystem-explained

Partner Deals

DeleteMe: 20% off removing your personal info from the web

Copilot Money: Free 2 months access to my favorite personal finance app with code HACKS2

Shopify: $1/month trial for the easiest e-commerce platform

Superhuman: Free month of the fastest and best email with code ALLTHEHACKS

Wispr Flow: Try effortless voice dictation for free

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

Resources Mentioned

Bilt 2.0

• Bilt Blue Card (Rates and fees here)
• Bilt Obsidian Card (Rates and fees here)
• Bilt Palladium Card (Rates and fees here)
• Bilt Cash
• Bilt Travel Portal
• Bilt Dining
• Bilt Home Design Collection
• Complimentary BLADE airport flight

Mastercard World Elite Benefits Guide

Award Search Tools

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

Gopuff

BevMo!

Rakuten ($50 bonus here)

Robinhood Gold Card

Frequent Miler Article: Bilt Housing Payments

ATH Podcast

• Luxury Hotel Upgrade Program
• Ask Chris Anything!
• Leave a review: Apple Podcasts | Spotify
• Email for questions, hacks, deals, and feedback: [email protected]

Full Show Notes

(00:00) Introduction

(02:28) What Makes Bilt Rewards Different

(07:03) How to Earn Bilt Points Without a Credit Card

(13:52) Referral Bonuses and Earning Limits

(14:17) How Rent and Mortgage Payments Work

(16:06) Earning Through the Bilt Neighborhood Network

(17:16) Earning Without a Card: The Real Tradeoffs

(17:46) How Bilt Point Redemptions Actually Work

(21:39) Transfer Partners and When Bonuses Matter

(24:18) How Bilt Status and Elite Tiers Work

(25:32) What Each Bilt Status Level Unlocks

(31:49) A Major Caveat With the New Bilt Cards

(34:36) Breaking Down the Current Bilt Card Lineup

(35:33) Bilt Blue Card

(37:34) Bilt Obsidian Card

(41:19) Bilt Palladium Card

(48:59) Housing Payments and What Changed

(50:16) Earning Based on Billing-Cycle Spend

(55:18) The Original Fee-Free Model

(59:26) Cash-Out and Statement Credit Options

(01:08:44) Simplifying the New Bilt Choices

(01:14:21) The Bilt Silver Lining

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

#263: Chris breaks down exactly how he’s earned millions of points and miles, and why simplicity matters more than optimization. He covers signup bonuses, spending strategies, credit score impacts, business cards, cash-back alternatives, and how to decide when a card (or perk) is actually worth it.

Link to Full Show Notes: https://chrishutchins.com/points-and-miles-simplified-credit-cards

Partner Deals

Fabric: Affordable term life insurance for you and your family

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

Gusto: Free 3-month trial of the #1 payroll software

Notion: Try Notion Agent free to automate tedious tasks and streamline your work

Gelt: Skip the waitlist on personalized tax guidance to maximize your wealth

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

Resources Mentioned

Credit Cards: Best Cards Page

• Alaska Airlines Visa®
• American Express® Green Card
• American Express Platinum Card for Schwab
• Atmos™ Rewards Summit Visa Infinite® Card
• Bank of America® Premium Rewards® Elite
• Bank of America® Unlimited Cash Rewards
• Bilt Palladium Card (Rates and fees here)
• Capital One Venture X Business
• Capital One Venture X Rewards Credit Card
• Citi® / AAdvantage® Executive World Elite Mastercard®
• Coinbase One Card
• Costco Anywhere Visa® Card by Citi
• Hilton Honors American Express Aspire Card
• Robinhood Gold Card
• The Business Platinum Card® from American Express
• U.S. Bank Altitude® Reserve Visa Infinite® Card
• Venmo Credit Card
• Wells Fargo Autograph℠ Card

Rakuten: Free $50 here

Business Payment Platforms: Plastiq | Melio

IRS Authorized Payment Providers

• Pay1040
• ACI Payments

Reddit: Credit Card Spend Needed to Achieve Each Airline Status Tier

ATH Podcast

• Chris' Credit Card Optimizer Tool
• Ask Chris Anything!
• Membership
• Gift Card Site
• Ep #164: Earn Points Paying Taxes with a Credit Card (+ Latest Deals/News)
• Ep #200: Debunking Tax Myths, Avoiding Audits and Maximizing Savings with Jasmine DiLucci
• Ep #221: Deep Dive on Credit Reports, Scores, and Their Real-World Impact
• Ep #247: Deep Dive on Bank of America Credit Cards (Up to 5.25% Cash Back)
• Ep #248: How to Stop Over-Optimizing and Focus on What Matters with Tim Ferriss
• Ep #258: My Top 5 Mistakes with Points & Miles
• Ep #261: Goals, Tools, and Mindset Shifts for a Better 2026 with Kevin Rose
• Leave a review: Apple Podcasts | Spotify
• Email for questions, hacks, deals, and feedback: [email protected]

Full Show Notes

(00:00) Introduction
(01:26) How Chris Has Earned 15+ Million Points
(03:46) Why Signup Bonuses Still Matter More than Everything Else
(05:04) The Role Everyday Spending Actually Plays
(08:42) When Transfer Bonuses Are Worth It
(12:24) How Chris Leverages Referral Bonuses
(13:24) What Having "Too Many" Credit Cards Really Does to Your Credit Score
(16:13) How Many Signup Bonuses per Year Is Reasonable?
(16:44) Why Spend Requirements Are the Real Bottleneck
(18:23) Approval Odds and Timing Applications
(22:04) Getting Approved for Business Cards (Without A Business)
(27:23) Maximizing Rewards without Overcomplicating It
(30:18) When Cash Back Is the Better Option
(32:48) Best Cards for Big, One-Time Expenses like Weddings
(37:24) Making Sense of Card Rules and Restrictions
(38:13) Annual Fees: How to Decide if They're Worth Paying
(41:12) Paying Taxes with a Credit Card
(46:28) How to Think about Points if You Mostly Care about Hotels
(49:10) Is CLEAR Worth It?
(51:48) How DoorDash Credits Work
(53:25) Is There a Shortcut to Airline Loyalty Status?
(57:04) The Best Credit Card for Costco Spending
(59:19) Are the New Bilt Cards Actually Bad?

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#262: Learn how to navigate major changes in points and miles while maximizing travel rewards in 2026. Chris and Brian M cover Bilt 2.0, the Mesa card shutdown, how to evaluate annual fees, find award availability, and what’s likely (and unlikely) to change this year.

Link to Full Show Notes: https://chrishutchins.com/latest-on-points-miles-january-2026

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

Resources Mentioned

Bilt World Elite Mastercard® (Rates and fees here)

Bilt 2.0

• Bilt Blue Card (Rates and fees here)
• Bilt Obsidian Card (Rates and fees here)
• Bilt Palladium Card (Rates and fees here)

Rove Miles

Silo Markets

Rakuten ($50 bonus here)

Kalshi Prediction Market

Alila Ventana Big Sur

The Big A## Calendar

Award Search Tools

• Award Wallet
• Points Path Chrome Extension
• Google Flights
• AwardTool ($20 off annual plans with code ALLTHEHACKS)
• Expert Flyer

ATH Podcast

• Leave a review: Apple Podcasts | Spotify
• Email for questions, hacks, deals, and feedback: [email protected]

Full Show Notes

(00:00) Introduction

(01:27) Reactions to Bilt’s New Card Lineup

(04:08) Breakdown of the 3 New Bilt Cards

(05:14) Should You Convert, Apply Fresh, Or Keep the Wells Fargo Card?

(08:16) Questions Around Bilt Cash

(09:50) The Bilt Card Chris Is Leaning Towards

(15:03) Why Bilt's New Earnings Might Be Better Than It Looks

(20:03) Mesa's Overnight Shutdown

(24:25) Silo Markets Brokerage Bonus

(29:54) What’s Coming Up in 2026 For Points, Loyalty, And Cards

(32:25) Thoughts on the Southwest Companion Pass

(35:26) Implications of the Proposed 10% Interest Rate Cap on Credit Cards

(38:19) Will Points Tools Get Better in 2026?

(40:02) Why 2026 Might Be Quiet on Major Credit Card Changes

(43:18)  How Brian Decides Whether an Annual Fee Card is Worth Keeping

(46:50) Chris’ Order of Operations For Analyzing Cards

(51:42) Ways to Plan A Trip Using Points

(57:49) How Brian Leverages Flexibility for Travel

(01:00:04) Strategies for Booking Flights

(01:03:23) The Best Award Flight Search Tools

(01:04:58) Booking Hotels With Points

(01:09:38) Timeshares: When They Make Sense (and When They Don’t)

(01:11:51) Using Alerts to Monitor Award Availability

(01:13:12) Changing the Connecting City After Booking a Flight

(01:15:14) Business Cards for Personal Spend (and Vice Versa)

(01:17:09) What to Do When You Stop Getting Approved for Cards

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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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#261: Chris and Kevin reflect on 2025’s biggest wins and lessons, then dive into how they're planning 2026. They share their goals, the tools they're using, and why they're designing a year that’s easier, not just more optimized.

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/reflecting-and-planning-2026

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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

Books

• The Wealth Ladder by Nick Maggiulli
• Rework by Jason Fried

Fizzy

Jesse Itzler: Plan An Incredible 2026 In 12 Minutes

Podcasts

• The Daily Churn
• New Modern Mom: Do you need a house manager?

Duolingo

Games Magazine Subscription

Bram Cohen Puzzles

The Big A## Calendar

ATH Podcast

• Newsletter
• Chris’ Card Optimizer Tool
• Ep #99: 7 Questions to Make 2025 Your Best Year Yet
• Ep #213: The 5 Types of Wealth with Sahil Bloom
• Ep #259: Choosing the Problems Worth Struggling For with Mark Manson
• Leave a review: Apple Podcasts | Spotify
• Email for questions, hacks, deals, and feedback: [email protected]

Full Show Notes

(00:00) Introduction

(00:45) Kevin's 2025 Goals & How They Came to Fruition

(04:34) Chris's Challenging End to 2025

(06:53) How Chris is Approaching Optimization in 2026

(09:33) Stepping Up Your Ability to Spend Money

(15:55) What Chris and Kevin Changed Their Minds About in 2025

(20:11) The Many Different Uses of AI

(29:16) Chris's Energy Generators and Drainers

(33:40) Kevin's Energy Generators and Drainers

(36:56) Decluttering for A Peace of Mind

(41:09) How To Identify The Boat Anchors in Your Life

(49:18) Chris's Hits and Misses in 2025

(52:10) Kevin's Hits and Misses for 2025

(54:19) How Kevin Plans His Year Ahead

(57:53) Outsourcing to Make Things Easier

(01:05:12) Focus on Making Lasting Memories

(01:06:34) Ways to Pick Up New Skills

(01:09:36) The Life Blender Concept

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.

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