#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

Fizzy

Jesse Itzler: Plan An Incredible 2026 In 12 Minutes

Podcasts

Duolingo

Games Magazine Subscription

Bram Cohen Puzzles

The Big A## Calendar

ATH Podcast

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

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