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.
Apr 22, 2025
I had not done an Ask Me Anything session in over a year which led to many questions on a wide variety of topics: macro, marketplaces, AI, fundraising, wealth management, education, island shopping, India, how to lose your accent, adventure travel, climate tech, the state of VC, and much more.
Here are the key...
Dec 16, 2024
Given that I have been building and investing in marketplaces for 26 years you might think that everything that needed to be built has already been built, but nothing could be further from the truth. In many ways, we are still at the beginning of the marketplace revolution with lots of exciting new trends.
In this...