About

Troy Henikoff has spent his career starting, building, and backing companies. He is Managing Director of MATH Venture Partners and teaches entrepreneurship at Northwestern University's Kellogg School of Management.

In 2010 Troy co-founded Excelerate Labs, the accelerator that became Techstars Chicago in 2013. He remains a senior advisor to Techstars and helped relaunch Techstars Chicago in 2026. He also serves on the board of 1871, the Chicagoland Entrepreneurial Center, and on the boards of many early-stage startups.

Before that, Troy was a serial founder and operator. He co-founded and ran SurePayroll, the nation's first online payroll company, later acquired by Paychex. He was CEO of OneWed.com, President of Amacai, and President of Systemetrics, built the technology behind Jellyvision's “You Don’t Know Jack!”, and started his first company, Specialized Systems and Software.

He holds an engineering degree from Brown University and a master’s in Project Management from Northwestern.

Somewhere along the way he noticed he was answering the same questions over and over. How much should I raise, and when? What does a real financial model look like? What are investors actually asking when they ask about your CAC? Rather than answer them one founder at a time, he started filming the answers — a few minutes each, one question at a time, usually at a whiteboard. That became MATH 101: a decade of short, specific lessons on the unglamorous mechanics of building a company.

This site gathers that work in one place and makes it searchable. The lessons were scattered across years of blog posts, and most of what matters was said out loud rather than written down — so the video mattered more than the text around it, and none of it was easy to find when you needed it. Now it is organised the way a founder actually arrives: by the problem in front of you.