November 5, 2025
The Real Match: Beating the Self That’s Afraid to Lose
Last month, while speaking with an editor from an international publication, she said to me, “Our theme for this issue i...
October 13, 2025
What a Decade of Investing Taught Me
2025 marks the tenth anniversary of founding Cherubic Ventures. When I first stepped into early-stage investing, I belie...
September 15, 2025
Story Crafting Is the New Competitive Edge
While teaching a Leadership course at an international high school in Japan, I witnessed something that left a deep impr...
August 14, 2025
A Campus Conversation That Lingers
This summer, while visiting Columbia University, I struck up a casual conversation with a sophomore studying computer sc...
July 17, 2025
If You’re Starting College in 2025
Dear Matt, Congratulations on starting college in 2025! I know you’re feeling both excited and a little overwhelmed righ...
June 24, 2025
AI Can’t Compute the Value of Trial and Error
In an era where AI is rapidly permeating every aspect of life and work, I often reflect not only as an investor ponderin...
May 28, 2025
Do founders still need us?
After watching Warren Buffett’s final annual shareholder meeting, one question kept looping in my mind: Will I be replac...
April 28, 2025
A Letter to the Future Leader: Learn What AI Never Will
Dear Future Leaders: If I could leave you with one truth for the world you’re inheriting, it’s this: In the age of AI, h...
March 26, 2025
Can You Outsmart AI? The New Rules of Learning
In 2019, I talked about “unlearning”—the ability to let go of old ideas—as a key skill for the future workfo...
February 26, 2025
Beware of Outsourcing Your Brain to AI!
Generative AI has revolutionized the way we work, offering incredible convenience. But with this convenience comes a ris...