All the Hacks: Money, Points & Life

#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/ Partner Deals Vuori: 20% off the most comfortable performance apparel I've ever worn Gelt: ⁠Skip the waitlist on personalized tax guidance to maximize your wealth Fora: Become a Fora Advisor today Wispr Flow: ⁠Try effortless voice dictation for free 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 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: [email protected] 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 ⁠⁠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

#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/ Partner Deals Copilot Money: ⁠Free 2 months access to my favorite personal finance app with code HACKS2 Kindred: House swap & home exchange with no membership fee Fabric: ⁠Affordable term life insurance for you and your family Bilt Rewards: ⁠Earn the most valuable points when you pay rent 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 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: [email protected] 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 ⁠⁠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

#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/ Partner Deals Kindred: House swap & home exchange with no membership fee Quince: Affordable luxury essentials with free shipping + 365 day returns 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: [email protected] 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. Learn more about your ad choices. Visit megaphone.fm/adchoices

#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/ Partner Deals NetSuite: ⁠Free KPI checklist to upgrade your business performance LMNT: ⁠Free sample pack of my favorite electrolyte drink mix DeleteMe: ⁠20% off removing your personal info from the web Zocdoc: Find and instantly book a doctor you love today 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 Silo Markets⁠ (← 250k 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: [email protected] 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 ⁠⁠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

#297: Learn how to turn small talk, awkward encounters, and everyday logistics into conversations that actually matter. Chris and Vanessa explore the chemistry behind great conversations, how to find the topics that make people light up, and the three levels of conversation that lead to deeper connection. Vanessa Van Edwards is a behavioral researcher, bestselling author of Captivate and Cues, and founder of Science of People. She teaches at Harvard, and her new book, Conversation: How to Connect with Anyone and Make Every Interaction Count, is available now. Link to Full Show Notes: https://chrishutchins.com/vanessa-van-edwards-better-conversations/ Partner Deals Bilt Rewards: ⁠Earn the most valuable points when you pay rent Fora: Become a Fora Advisor today Gusto: ⁠Free 3-month trial of the #1 payroll software Fabric: ⁠Affordable term life insurance for you and your family 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 Vanessa: Website | X | Instagram | YouTube Captivate: The Science of Succeeding with People Cues: Master the Secret Language of Charismatic Communication Conversation: How to Connect with Anyone and Make Every Interaction Count ProSocial Research and Frameworks Dr. Dan McAdams CANDOR Corpus Malcolm Gladwell's MasterClass Shows and People SmartLess podcast (with Sacha Baron Cohen) The Howard Stern Show ATH Podcast #46: Mastering the Secret Language of Charismatic Communication with Vanessa Van Edwards #256: The Easy Way to Build and Maintain Meaningful Relationships with Nick Gray #123: Traveling to Save Money, Betting on Yourself, and Streamlining Life Decisions with Nuseir Yassin 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: [email protected] Full Show Notes (00:00) Introduction (00:45) How to Make Every Conversation Matter (02:12) The DOS Cocktail: The Chemistry of a Great Conversation (05:15) Turning Everyday Interactions Into Meaningful Conversations (14:05) Treating Small Talk Like a Treasure Hunt (15:31) How to Start a Meaningful Conversation (20:53) Can Conversational Courage Go Too Far? (23:08) A Framework for Asking Better Questions (27:01) Why You Can't Skip Straight to Deep Conversation (30:20) Level 1: General Traits (32:11) Level 2: Personal Concerns (32:40) Level 3: Your Self-Narrative (34:48) How to Be Conversationally Generous (37:18) What to Do When You're Just Not Clicking (38:54) How to Become a Better Conversational Storyteller (41:18) Turning Any Conversation Into a Chance to Learn (43:04) Mindset Tricks for Warmer, Easier Conversations (47:00) How to Know If You’re Talking Too Much (51:31) Why Some "Great" Questions Are Actually Hard to Answer (53:35) The Ideal Length of a Conversational Turn (55:12) How Talking to AI Is Changing How We Talk to People (58:53) Using AI to Become a Better Conversationalist (01:01:02) Deeper Conversations With Your Partner (Beyond the Logistics) (01:07:51) Did This Feel Like a Real Conversation? (01:08:35) What to Expect from Vanessa's New Book 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