14 January 2026
Goals, Tools, and Mindset Shifts for a Better 2026 with Kevin Rose
All the Hacks: Money, Points & Life
About
#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
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