Tom Firestine

Principal / Calculated Risk Advisors, LLC

Tom is the cofounder and principal at Calculated Risk Advisors, a boutique professional liability insurance broker based in Chicago. He also holds operating positions at Nameless Ventures (early stage investments), Percipient (legal tech) and Calculated Risk Analytics (actuarial consulting). Prior to starting his entrepreneurial journey he held positions in the insurance industry at CNA, Marsh and OneBeacon.

In addition to a number of insurance and tech industry designations Tom earned a BSBA in Finance from The Ohio State University and a MBA in Finance, Econometrics & Statistics from the University of Chicago. He is involved in several Midwestern tech accelerators, chairs the risk management committee of the Boy Scouts of America Pathway to Adventure Council and is a doting father to his two young girls.


The Economic Club of Chicago
33 N. Dearborn Street
Suite 1700
Chicago, IL 60602
Monday through Friday  /  9am–5pm