All the Hacks: Money, Points & Life

#302: Learn why Hilton can be one of the most rewarding programs around and exactly how to get the most out of it. Chris breaks down what Hilton points are really worth after years of devaluations, how the four Amex Hilton cards stack up, and why uncapped free night rewards are his favorite perk. Plus, the sweet spots for redeeming points, family-friendly perks and points pooling, and why buying points on sale might be the best arbitrage around.
Link to Full Show Notes: https://www.chrishutchins.com/hilton-honors-deep-dive/

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Resources Mentioned
Hilton
Hilton Honors
Hilton Credit Cards
Hilton Honors Experiences
Hilton Honors Giving Back
Hilton Honors Dining
Hilton brands & partners
Small Luxury Hotels of the World (SLH)
All Hilton brands
AutoCamp
Booking & search tools
Gondola
seats.aero
rooms.aero
MaxMyPoint
PointsYeah
AwardTool
Awayz
StayWithPoints
Capital One Shopping
Further reading
What Are Hilton Points Worth?
Hilton Price Match Guarantee: How I Saved $550+ Making 2 Best Rate Guarantee Claims
ATH Podcast
#244: How I Saved $10,000+ on Luxury Hotels
#289: How We Booked a $20,000 Vacation With Points
#294: Deep Dive on World of Hyatt: Points, Perks and Status
#300: Luxury Europe for 70% Less: Switzerland & Lake Como with Amy Fox
Best Hilton Cards Page
Hotel Upgrade Program
Best Cards Page
Gift Cards Page
Newsletter
AMA: Submit Questions
Leave a review: Apple Podcasts | Spotify
Email for questions, hacks, deals, and feedback: podcast@chrishutchins.com

Full Show Notes
(00:00) Introduction
(00:38) Why Hilton Still Earns a Spot in My Arsenal
(03:43) How Hilton Points Compare to Hyatt, Marriott & IHG
(05:44) Hilton’s Ongoing Point Devaluations
(06:09) Hilton’s Footprint: 28 Brands and 9,000+ Hotels
(08:59) How to Earn Hilton Points
(11:53) No Award Chart: Standard vs. Premium Rewards
(13:52) Fifth Night Free, No Resort Fees and Other Award Perks
(16:14) The Worst (and Best) Non-Hotel Uses for Points
(17:17) Transferring Points from Amex and Bilt
(19:44) The No-Annual-Fee Hilton Honors Card
(21:17) The Hilton Surpass Card
(22:38) The Hilton Aspire Card
(24:53) Stacking Free Nights by Upgrading Cards
(27:13) The Hilton Business Card
(30:54) Why Free Night Rewards Are Hilton’s Best Perk
(34:19) Are Hilton Credit Cards Worth the Spend?
(36:45) Hilton Status Tiers: Silver, Gold and Diamond
(40:44) The New Diamond Reserve Tier 
(42:29) Why Hilton Upgrades Are Hard to Count On
(46:00) Breakfast, Lounges and Milestones: Hilton’s Weakest Perks
(50:05) Where to Find Hilton’s Redemption Sweet Spots
(54:33) Booking Tactics: Price Drops and the Price Match Guarantee
(58:27) Stacking Promos, Card Offers and Shopping Portals
(01:00:05) Confirmed Connecting Rooms and Other App Perks
(01:01:52) Pooling Points with Family and Friends
(01:02:52) The Hilton Points Arbitrage Anyone Can Use
(01:05:27) More Ways to Earn and Save at Hilton
(01:06:53) The Case Against Hilton
(01:08:00) The Case for Hilton
(01:09:18) Bottom Line: How to Use Hilton
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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.

#301: Chris revisits the rules, products, and strategies he’s changed his mind about, and what he’s doing differently now. He covers a surprising airfare pricing quirk, major updates from U.S. Bank, Bilt, Alaska and Bank of America, and why he’s scaling back his AI experimentation. Plus, new thoughts on browsers, AR glasses, skincare, and hiring.
Link to Full Show Notes: https://www.chrishutchins.com/things-i-changed-my-mind-on-2026/

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

Resources Mentioned
Articles
Booking Domestic Flights One-Way? It’s Costing You More (Again)
AI & Building Tools
OpenClaw
Claude
ChatGPT
Instinct
Meta Muse
Dots
Grok
Browsers
Arc
Dia
Google Chrome
QuicKey tab switcher
AR Glasses & Tech
XREAL 1 Pro
VITURE
Meta Ray-Ban glasses
Apple Vision Pro
iPhone Duo
Robinhood Gold Card
CardPointers
Wild Roman

ATH Podcast
#247: Deep Dive on Bank of America Credit Cards (Up to 5.25% Cash Back)
#264: Deep Dive on Bilt Rewards and New Bilt 2.0 Cards
#265: I Built an AI Assistant That Works While I Sleep
#271: How to Actually Live the Life You're Optimizing For with Sahil Bloom
#290: The New Rules of Points & Miles in 2026 with Brian M
CardTool
Hotel Upgrade Program
Best Cards Page
Gift Cards Page
Newsletter
AMA: Submit Questions
Leave a review: Apple Podcasts | Spotify
Email for questions, hacks, deals, and feedback: podcast@chrishutchins.com

Full Show Notes
(00:00) Introduction
(00:45) Why One-Way Flights Can Cost More Than a Round Trip
(05:23) U.S. Bank Finally Adds Transfer Partners 
(07:38) New Ways to Use Bilt Cash
(12:42) Going All In on Alaska (Again)
(18:46) Why Bank of America Cards Could Become Great Alaska Cards
(23:53) Accidentally Ending Up with a $2k Gold Credit Card
(27:43) The End of Auto-Adding Every Amex Offer
(30:16) Why Building Your Own AI Tools Often Isn't Worth It
(36:18) Leaving Arc, Trying Chrome, and Switching to Dia
(39:27) The AR Glasses Worth Wearing on Every Flight
(41:52) A Skincare Routine Simple Enough to Stick
(43:58) Rethinking Hiring a Full-Time Employee
(46:08) Is Video Worth It for This Podcast?

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.

#300: Chris and Amy break down how they planned an unforgettable trip to Switzerland and Lake Como mostly on points, miles, and free-night certificates. They share how speculative bookings and award alerts landed them better business class flights, the rental car hack that avoided a cross-border drop-off fee, and one of the best uses of Hilton points around. Plus, an inside look at a fairy tale hotel for families in Switzerland.
Link to Full Show Notes: https://www.chrishutchins.com/switzerland-italy-family-trip-points/

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

Resources Mentioned
Hotels
Märchenhotel Braunwald
Grand Hotel Victoria
Victoria Beach Club
Park Hyatt Milan
Hyatt Regency Mainz
Park Hyatt Tokyo
Cap Rocat

Articles & Videos
Amazing: Grand Hotel Victoria Concept & Spa on Lake Como
The Märchenhotel on Instagram

ATH Podcast
#107: Italy Unlocked: Insider Tips, Must-See Destinations and Booking Flights/Hotels on Points with Leigh Rowan
#276: Saving $30K+ on the Perfect Spring Break Japan Trip with Amy Fox
#290: The New Rules of Points & Miles in 2026 with Brian M
Hilton Cards
Hotel Upgrade Program
Best Cards Page
Gift Cards Page
Newsletter
AMA: Submit Questions
Leave a review: Apple Podcasts | Spotify
Email for questions, hacks, deals, and feedback: podcast@chrishutchins.com

Full Show Notes
(00:00) Introduction
(00:47) How a Fairy Tale Hotel Sparked Our Trip to Europe
(03:22) Booking Business Class to Europe with Points
(09:03) Setting Award Alerts to Find Better Flights
(14:51) Using Up Avianca Miles for a Better Flight
(17:22) Keeping Return Flights Open Until the Last Minute
(18:39) The Trick to Avoid Cross-Border Rental Car Fees
(20:55) Booking Switzerland's Märchenhotel Without Points
(23:10) Why We Paired Switzerland with Lake Como
(26:14) The Math Behind Hilton Points and Free Night Certificates
(34:02) Inside the Grand Hotel Victoria
(36:55) The Best Breakfast Buffet and Dining in Menaggio
(39:26) Why Menaggio Beats Bellagio
(42:10) European Beach Clubs with Kids
(43:34) Gelato, Mini Golf and Other Things to Do in Italy
(45:27) Is the Grand Hotel Victoria Worth It for Families?
(48:51) The Märchenhotel: Switzerland's Fairy Tale Hotel
(49:57) What Makes the Märchenhotel Great for Parents and Kids
(57:06) Hiking, Via Ferratas and Ropes Courses in Braunwald
(01:02:31) Changing Plans and Skipping Milan
(01:05:44) A Quick Stop in Mainz Before Flying Home
(01:07:15) Flying Swiss vs. Condor Business Class
(01:10:49) What It's Like Traveling with Another Family
(01:14:02) What the Whole Trip Cost
(01:15:24) Why We're Booking Trips a Year Out

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.

#299: My top 10 takeaways from a retreat for high-net-worth investors, which covered money, health, AI, parenting, relationships, and more. We explore why what you measure shapes your behavior, how to start using AI agents, why simple rules beat perfect plans, how to teach kids about money, and why “later” may be the most expensive word in your vocabulary.
Tad Fallows is the co-founder of Long Angle, a private community for investors with $3 million or more in investable assets. He previously co-founded iLab Solutions, a research software company acquired by Agilent Technologies.
Link to Full Show Notes: https://www.chrishutchins.com/10-lessons-money-parenting-ai-long-angle/

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Wispr Flow: ⁠Try effortless voice dictation for free
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
Long Angle

People & Books
Sahil Bloom
The 5 Types of Wealth by Sahil Bloom
Sahil Bloom's post on the 3 Levels of Listening
Andrew Taylor

Health
Oura Ring

ATH Podcast
#253: 10 Lessons That Challenged My Thinking on Money and Life
#297: Have Better Conversations and Build Deeper Connections with Vanessa Van Edwards
Hotel Upgrade Program
Best Cards Page
Gift Cards Page
Newsletter
AMA: Submit Questions
Leave a review: Apple Podcasts | Spotify
Email for questions, hacks, deals, and feedback: podcast@chrishutchins.com

Full Show Notes
(00:00) Introduction
(02:04) What You Measure Dictates What You Do
(05:57) Don't Let the Optimal Get in the Way of the Beneficial
(15:13) How to Get Started with AI Agents
(26:28) Why Established Managers Outperform Emerging Ones
(35:07) Good Plans Die in the Paperwork
(39:48) Simple Rules You'll Follow Beat Perfect Rules You Won't
(46:54) T.U.N.E. Parenting: Balancing Connection with Boundaries
(58:23) Your Environment Beats Your Willpower
(01:04:11) Talk Less and Ask Better Questions
(01:11:17) "Later" Is the Most Expensive Word
(01:18:55) The Meta Takeaway: Pick One Thing and Start Today

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.

#298: Chris breaks down how to earn airline miles and transferable points on money you’re already saving or investing (and whether the rewards are actually worth the tradeoffs). He compares mileage-earning bank accounts from Bask, United and Alaska, the new Bank of America and Alaska transfer partnership, Silo’s brokerage rewards program, and Symphony’s higher-yield approach. Plus, the welcome offers ending this fall that change the first-year math, and a short interview with Symphony's founders.
Link to Full Show Notes: https://chrishutchins.com/earn-points-on-savings/

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

Resources Mentioned
Silo Markets (← 250k Welcome Bonus)
Symphony (← Referral Bonus)
Bask Bank
Atmos debit card (← 20% off coupon)
Odynn
point.me

ATH Podcast
#131: Maximize Earnings on Cash, CD Ladders, Bank Bonuses, Bulk Buying, and Automating Returns
#195: 50+ Ways to Earn More Points and Miles Without Spending More
#262: Points & Miles in 2026: What's New, What's Dying & What's Next with Brian M
#288: Where to Keep Your Cash for the Highest Return
Hotel Upgrade Program
Best Cards Page
Gift Cards Page
Newsletter
AMA: Submit Questions
Leave a review: Apple Podcasts | Spotify
Email for questions, hacks, deals, and feedback: podcast@chrishutchins.com

Full Show Notes
(00:00) Introduction
(00:50) How to Earn Points on Your Savings
(05:01) Bank Accounts That Pay Airline Miles
(05:41) Earning American Miles with Bask Bank
(14:13) Why United's Mileage Debit Card Falls Short 
(17:09) Alaska’s Upcoming Rewards Banking Account
(17:48) Boosting Bank of America Points, Now Transferable to Alaska
(20:29) How Silo Pays Points on Your Brokerage Account
(26:22) Changes Coming to Silo on November 1st
(32:40) Silo's New Welcome Bonus
(35:52) Can You Trust Silo With Your Investments? 
(36:31) Earning 5% or 5X Points with Symphony
(38:52) Where Your Money Actually Goes at Symphony
(39:22) Bucket 1: Treasury Bills
(40:18) Bucket 2: CLOs
(41:37) Bucket 3: Private Credit
(43:24) Bucket 4: Crypto Lending
(46:20) Pooled Accounts and SIPC Protection
(46:57) What the Crypto Wallet Does (and Doesn't) Protect
(47:33) How Fast You Can Get Your Money Out
(49:17) Risk #1: The Rate Gets Cut
(49:55) Risk #2: Withdrawals Slow Down
(50:17) Risk #3: You Lose Part of Your Investment
(51:05) Risk #4: An FTX-Style Collapse
(51:49) My Overall Take on Symphony
(54:21) Breaking Down Symphony's Welcome Offer
(57:04) Recap: Mileage Bank Accounts
(58:38) Recap: Silo
(59:57) Recap: Symphony
(01:02:02) Interview with Symphony's Founders
(01:04:01) How Symphony Layers Its Risk Protection
(01:08:02) What Happens If Everyone Withdraws at Once
(01:09:54) Why the Blockchain Ledger Matters If Symphony Goes Away
(01:16:15) What’s Next: Transfer Partners, Experiences and AI Booking

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.