Mar 23, 2026
It’s been a year since my last Ask Me Anything
session. A lot has happened since then across AI, marketplaces,
macro, and the broader tech ecosystem.
Here are the questions we covered:
· 4:22 Why does AI feel so widely feared or disliked right now?
· 8:48 Why is AI driving massive progress while politics...
Mar 9, 2026
Over the past few weeks, a growing narrative has emerged arguing that AI could destabilize the economy and disrupt entire business models. Last week, I published my view that AI is far more likely to be a productivity revolution than an economic collapse.
But what does this mean specifically for marketplaces?
Many...
Jan 19, 2026
I had the pleasure of chatting with Zach Resnick, the founder and CEO of Ascend (formerly FlyFlat), a membership program for frequent travelers that eliminates 90% of travel decisions and saves 35% off biz/first class flights.
Ascend has been helping my partners Jose and Jeff with all their
travels for a couple years...
Jun 20, 2025
The venture market is in flux. AI is booming while the rest of venture is in the dumps. Venture capital as an asset class is evolving and retrenching. Fewer deals are happening at higher prices. New marketplace types are emerging. AI is impacting marketplaces in unexpected ways and new technologies are coming of age....
Jun 9, 2025
Clutch has had an incredible ride. As the “Carvana of Canada” it was a highflier in 2021. It had a brush with death in 2023 and effected an incredible turnaround. They are now once again on a tear. Dan Park, Clutch’s Founder & CEO, joined us to share all the lessons learned along the way.