Goals, Tools, and Mindset Shifts for a Better 2026 with Kevin Rose

Goals, Tools, and Mindset Shifts for a Better 2026 with Kevin Rose

Author: Chris Hutchins January 14, 2026 Duration: 1:09:45
All the Hacks: Money, Points & Life
BusinessCultureEducationInvestingPlacesSocietySociety & CultureTravel
#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 Partner Deals Wispr Flow: Try effortless voice dictation for free LMNT: Free sample pack of my favorite electrolyte drink mix 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 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 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: podcast@chrishutchins.com 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 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: 100

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All the Hacks: Money, Points & Life
Podcast Episodes
The Cost of Always Optimizing with Chris and Amy [not-audio_url] [/not-audio_url]

Duration: 1:12:10
#254: Chris and Amy share a candid look at their life together as two optimizers. They discuss everything from family finances and teaching their kids about money to managing their health, work, and travel. Link to Full…
10 Lessons That Challenged My Thinking on Money and Life [not-audio_url] [/not-audio_url]

Duration: 59:23
#253: My top 10 takeaways from a retreat for high-net-worth investors, which will cover investing, managing risk, investing in your health, building meaningful relationships, parenting with purpose, and defining success…
Family Travel on Points: Tips, Tricks and Tactics with Nick Reyes [not-audio_url] [/not-audio_url]

Duration: 1:25:55
#252: Chris and Nick share strategies to make family travel affordable and stress-free with points and miles. They cover how to find multiple award seats, book business class for families, and their best tips for traveli…
How to Focus on What Matters and Let Go of the Rest with Ryan Holiday [not-audio_url] [/not-audio_url]

Duration: 58:43
#251: Discover why Stoicism matters more than ever and how to make it part of your daily life. We share practical ways to focus on what you can control, build resilience, and cultivate the four Stoic virtues: courage, se…
Earn More Points in Multiplayer Mode with Kai [not-audio_url] [/not-audio_url]

Duration: 50:10
#249: 3x your points and miles with a multiplayer strategy. We break down how to earn, manage, and maximize rewards with a partner, family, or friends. Plus learn how to handle the logistics, emotions, and systems that m…
How to Stop Over-Optimizing and Focus on What Matters with Tim Ferriss [not-audio_url] [/not-audio_url]

Duration: 1:33:48
#248: Learn to escape the trap of over-optimizing and design a more meaningful life. We explore setting boundaries, resetting priorities, and turning failure into fuel for success. We also dive into Tim’s creative proces…
Deep Dive on Bank of America Credit Cards (Up to 5.25% Cash Back) [not-audio_url] [/not-audio_url]

Duration: 1:02:24
#247: Chris dives into Bank of America’s credit card lineup and why he has 5 different BoA cards right now. He'll go over how the Preferred Rewards program can help you earn unlimited 3.3% back on everything. Finally, he…
Contrarian Takes on Money, Risk, and Retirement with Tyler Gardner [not-audio_url] [/not-audio_url]

Duration: 1:11:50
#246: Today we explore contrarian takes on budgeting, the 4% rule, retirement planning, and the risks of blindly investing in bonds. We also cover strategies for investing, spending, and rethinking how to use money with…
How Much Are Points and Miles Worth in 2025? [not-audio_url] [/not-audio_url]

Duration: 1:06:42
#245: Ever wonder what points are really worth? I'll break down the different types of points, how to calculate their value, and the biggest mistakes people make along the way. You’ll also learn when cash back might be t…

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