Tommy graduated from West Point in 2011 and served as an infantry officer in the US Army until 2019. Tommy left the Army as a Captain having deployed four times, including two deployments to Afghanistan as a Ranger conducting raids against high value insurgents.

Following his Army career, Tommy attended The Wharton School where he graduated with a Masters in Business Administration in May 2021.

After graduating from Wharton in 2021, Tommy founded Sierra Succession to acquire and operate a small business using the "self-funded" ETA model. In August of 2022, he acquired Packaging Specialties, a custom retail packaging manufacturer in Newburyport, MA.