Money: What Each Generation Gets Right (& Wrong) with Ben Carlson

Money: What Each Generation Gets Right (& Wrong) with Ben Carlson

Author: Chris Hutchins June 25, 2025 Duration: 1:03:32
#233: Explore how different generations approach money and what they get right (and wrong) about saving, investing, spending, and building wealth. We dig into the psychology of money across generations and share practical lessons on homeownership, retirement, automation, points inflation, and more. Ben Carlson is the Director of Institutional Asset Management at Ritholtz Wealth Management. He runs the popular financial blog, A Wealth of Common Sense and is the author of four books on investing and personal finance. He also co-hosts one of my favorite podcasts: Animal Spirits. Link to Full Show Notes: https://chrishutchins.com/financial-mindsets-across-generations-ben-carlson Partner Deals Superhuman: Free month of the fastest and best email with code ALLTHEHACKS Green Chef: 50% off your first meal kit with code 50ALLTHEHACKS Notion: Try Notion AI free to automate tedious tasks and streamline your work 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 Ben Carlson: Website | Animal Spirits Podcast | X Ben's Post: Financial Advice That Doesn’t Work Anymore Morningstar Column by John Rekenthaler Tim Ferriss Ep #815: Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips & More Award Travel Search Tools AwardTool: $20 off annual plans with code ALLTHEHACKS PointsYeah Points Path Chrome Extension Coinbase One: Join the waitlist here ATH Podcast Leave a review: Apple Podcasts | Spotify Email for questions, hacks, deals, and feedback: podcast@allthehacks.com Full Show Notes (00:00) Introduction (02:27) The Great Wealth Transfer From Boomers to Millennials (05:52) Financial Mindsets Across Different Generations (09:10) Current Status of the Housing Market (11:37) Spending Habits in the Travel Industry (14:28) Financial Lessons From Every Generation (19:09) Stock Market vs. Housing Market (25:41) Financial Advice That Doesn't Work Anymore (27:33) How to Learn to Spend Money and Enjoy It Now (31:39) The Spectrum of Coast FIRE (38:48) Ben's Take on Social Security: Is It Worth It? (41:25) How to Navigate the Current Market Volatility (47:08) How Demographic Changes Impact the Investment Landscape (50:27) Active vs. Passive Investing (52:45) Different Ways to Automate Your Finances (54:26) Credit Card Points Inflation and Its Impact (58:09) Credit Card Returns: Cash Back vs. Welcome Offers 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

Ever feel like there's a smarter, more efficient way to navigate your finances, your travels, and your daily routines? That's the core question driving All the Hacks: Money, Points & Life. Hosted by Chris Hutchins, this podcast is built on a simple, powerful idea: maximizing value doesn't mean sacrificing enjoyment. Instead, it's about the strategic choices that free up resources-both money and time-for what truly matters. Chris approaches life as a series of systems to be optimized, drawing from his own experience saving millions through meticulous analysis. The conversations here are practical and wide-ranging, moving seamlessly from credit card points strategies and investment philosophies to the less tangible hacks for personal fulfillment. You'll hear from a diverse roster of experts and icons, including Tim Ferriss, Tony Hawk, Codie Sanchez, and Gary Vaynerchuk, who all bring their unique perspectives on building wealth and designing a compelling life. Each episode feels like a focused workshop, offering actionable advice you can use immediately, whether it's planning a luxury vacation for a fraction of the cost or rethinking your approach to career and leisure. This isn't just about frugality; it's about unlocking freedom and excitement through smarter decisions. Tune in for a consistently insightful blend of tactical moves and deeper conversations that challenge the conventional trade-offs between spending, saving, and living well.
Author: Language: English Episodes: 274

All the Hacks: Money, Points & Life
Podcast Episodes
Stop Overthinking and Start Deciding with Derek Sivers [not-audio_url] [/not-audio_url]

Duration: 1:52:11
#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…
My Process for Booking Travel with Points & Miles [not-audio_url] [/not-audio_url]

Duration: 54:29
#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…
How to Actually Live the Life You're Optimizing For with Sahil Bloom [not-audio_url] [/not-audio_url]

Duration: 56:41
#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 partne…
Ski Trip Mishaps, AI Interior Design, Reflecting on Life and More [not-audio_url] [/not-audio_url]

Duration: 1:08:15
#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://…
Credit Cards: What's in My Wallet for 2026 [not-audio_url] [/not-audio_url]

Duration: 1:14:45
#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 us…
Why Change Is Hard and How to Make It Your Advantage with Maya Shankar [not-audio_url] [/not-audio_url]

Duration: 45:22
#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 to…
I Built an AI Assistant That Works While I Sleep [not-audio_url] [/not-audio_url]

Duration: 51:24
#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 eve…
Deep Dive on Bilt Rewards and New Bilt 2.0 Cards [not-audio_url] [/not-audio_url]

Duration: 1:15:43
#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…