Early in his career, Tomaino was an Associate at North Atlantic Capital, Businesss Development at Coinbase, and Principal at Runa Capital.  In August 2017, Tomaino became the Foudner and General Partner at 1confirmation, an early stage crypto fund.  The fund is backed by Mark Cuban . 
Tomaino is a graduate of The Governor's Academy and played football during his time in high school.   He attended Bowdoin College where he earned a BA in Economics is 2008.  He would later attain his MBA from the Yale School of Management .