Fliegel and his companies were named to Inc 5000, and awarded Inc “30 under 30”, Forbes "30 under 30", BBJ “40 under 40”, Finalist for Ernst & Young “New England Entrepreneur of the Year” and Sports Business Journal SportsTech Power Player.

He is the grandson of former professional basketball player Bernie Fliegel and godson of Guido Goldman, founder of the German Marshall Fund.

As a Senior he won the Jefferson Davis Book Award, Bowdoin's top prize for academic achievement in Government & Legal Studies.

As a 3-year starter and co-captain, he earned Team MVP, All-league, All-state, All-New England, and Jewish Sports Review All-American honors while leading Bowdoin to a 22–7 record (best in school history), the NESCAC Championship game, and the 2nd round of the Men's NCAA Division III Tournament.

CoachUp has been covered in outlets such as the Wall Street Journal,[7] USA Today,[8] the Boston Globe, and the Huffington Post.