All the Hacks: Money, Points & Life

#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

#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

#295: Chris shares the strategies he actually uses to earn, spend, and maximize millions of points and miles. He breaks down how many credit cards most people really need, his approach to booking award travel for a family, the rise of massive card-member flight discounts, when to pay cash vs. points, and some of his favorite—and most unusual—redemptions. Meghan Coyle and Sally French are the hosts of NerdWallet's Smart Travel podcast, a weekly show on travel news, loyalty programs and travel credit cards that helps listeners travel more and pay less. Link to Full Show Notes: https://chrishutchins.com/award-flights-card-strategy-nerdwallet Partner Deals Gusto: ⁠Free 3-month trial of the #1 payroll software Gelt: ⁠Skip the waitlist on personalized tax guidance to maximize your wealth LMNT: ⁠Free sample pack of my favorite electrolyte drink mix Wispr Flow: ⁠Try effortless voice dictation for free 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 NerdWallet Smart Travel podcast Meghan Coyle Sally French Award Search & Points Tools Seats.aero PointsPath (15% off with ALLTHEHACKS15) PointsYeah Shopping Portals, Gift Cards & Offers Rakuten Capital One Shopping Rove GCX SavenDeals ATH Podcast #290: The New Rules of Points & Miles in 2026 with Brian M Chris' Credit Card Optimizer 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 (02:06) How Chris Got Into Points & Miles (05:01) When Chris Became a Points & Miles “Expert” (07:25) Paying for a Wedding Video With Delta Miles (13:38) Why Chasing an Extra Point per Dollar Doesn't Move the Needle (15:34) The Optimal Two-Card Strategy (16:50) Maximizing Points Without Overspending (19:52) Should You Buy Gift Cards to Earn More Points? (22:36) Booking Award Travel for a Family (25:06) Chris’ Strategy for Finding Award Flights (27:34) Leveraging Flexibility and Award Search Tools (31:45) What to Do With Points If You Don't Want to Play the Game (34:30) Setting Alerts and Picking One Award Search Tool (37:01) The Huge Discounts Hidden Behind Airline Credit Cards (39:21) The Risks of Speculative Bookings (41:08) When Chris Breaks His Own Transfer Rule (45:15) The Easiest Way to Redeem Points When You Don't Want the Hobby (47:17) Are Hotel Redemptions Easier Than Flights? (51:07) The Real Math Behind Cash vs. Points (55:02) Chris's Rule of Thumb for Comparing Cash and Points (56:12) A Trick for Getting Refunds on Flights You Need to Cancel (59:03) Chris’ Take on the New Southwest 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