IIRC, JackO was the first buddy Simmons used to have on his podcast and was pretty engaging. Rather than trying to turn that into something more, JackO decided to play it conservative and did nothing more than take the occasional call from Bill. Now their classmate Joe House (who had all the same qualifications as JackO, AFAICT) is running around the country making podcasts about golf and food on the company dime, Cousin Sal turned predicting the lines with Simmons into various gambling podcasts and TV shows*, Bill is making a bajillion dollars, and JackO is still answering the "complex litigation" phone for the state of Connecticut. So I'd say that guy fucked himself quite effectively.
* I know Cousin Sal was already in show business through Kimmel, but I think "Bet the Lines" helped him significantly.