Goals, Tools, and Mindset Shifts for a Better 2026 with Kevin Rose
All the Hacks: Money, Points & Life
Splurging for Experiences
Chris explains opting for a Four Seasons trip, prioritizing memorable experiences over point-optimization.
#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
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Resources Mentioned
Kevin Rose: Diggnation | Newsletter
Books
- The Wealth Ladder by Nick Maggiulli
- Rework by Jason Fried
Jesse Itzler: Plan An Incredible 2026 In 12 Minutes
Podcasts
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
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