
He sold two fantasy sports businesses, watched DRAFT lose its place inside a larger company, and gathered the team to try again. At Underdog, Jeremy Levine is still working on the same question: how much more fun could following sports become?
A private basketball coach changed Jordan Fliegel’s path. From CoachUp to Acquisition Lab, he has been building ways for other people to get that same kind of help.

Nate Kontny is a Chicago-based serial founder, engineer, and writer who went from chemical engineering at UIUC to co-founding two Y Combinator companies (Inkling W06, Cityposh S11), running Highrise as CEO for Jason Fried, writing prolifically across Medium, HuffPost, and Fast Company, and building a suite of solo products - most recently AlliHat, a Safari extension embedding Claude AI directly in the browser. Currently Staff Engineer at Fivetran (post-Census acquisition), he is known for his radical transparency about failure, his 250-words-a-day writing discipline, and a philosophy that shipping imperfect work beats endless polishing.