Prior to co-founding Yelp, Simmons was a co-founder of PayPal, where he was a Lead Software Architect, and has been described as a member of the "PayPal Mafia." In 2014 he founded Learnirvana.
Before founding Yelp, Simmons had prior experience with PayPal, serving as a co-founder and Lead Software Architect, and being associated with the "PayPal Mafia." He later founded Learnirvana in 2014.