Bill Simmons is, without question, the most influential sports media figure of the 21st century. Given that, most of the following is well-established, but for those who don't know, Simmons: 1) grew up in Boston, and attended Holy Cross, 2) now lives in Los Angeles, and 3) almost never talks about college football.
Given all of the above, it takes a special confluence of events for The Sports Guy to devote 45 minutes of his podcast -- which ranks No. 2 on the Spotify sports charts, with episodes topping 300,000 downloads -- to an interview with an active college football coach, and it's a big deal when he does. Like, the former Holy Cross head coach also moving out to Los Angeles.
In Sunday's episode, Simmons visited Bob Chesney at UCLA's football facility, and most of the episode can be described as explaining college football to non-college football fans. But asking basic, open-ended questions can lead to great answers, including Chesney's explanation of how he builds culture based on constant competition.
Chesney described an A ha moment when reading Tom Verducci's book The Cubs Way, when Joe Madden described meeting long-cut minor leaguers years after the Cubs let them go. The prospects would ask why they were cut, Madden or a Cubs executive would provide the reason why, and they player would ask why he wasn't informed of his deficiency before it got him dismissed from the organization.
"I was like, You know what? This is what this has to be. Just constant feedback. Am I winning? Am I losing? Am I getting better?" Chesney recalled. "I don't need to compare myself to other people, I need to compare myself to myself a day ago. That's ultimately what we're trying to do here on a day-to-day basis. If you don't put them in situations to succeed and fail, then I think they're guessing. I say it all the time: the leading cause of success is well-managed failure. Any successful thing you did in your life, you probably failed at it first. It's got to cut a little bit. The leading cause of failure is mis-managed success. Now I feel like I've arrived, I'm entitled to this now, and what does that do.
"You can't build confidence if you don't give them moments to succeed, and have micro-successes over and over and over, every single day. And these micro-failures. So that they can get better and learn, and become something better than they were a day ago. That's ultimately what this whole thing is built on. We're not just competing for the hell of it and to embarrass people, we're doing it to have these micro-successes," he said.
In the offseason, players are drafted on to five teams, captained by the five fastest and five strongest Bruins. The results of the draft are published within the team, and each day one Bruin was pitted against another Bruin. After weeks of daily competition, mano-y-mano against a different teammate each day, the roster self-sorts in four groups.
Ultra-competitors: guys who are driven to win and bring others with them
Dominant competitors: guys who are driven to win, but don't bring others with them
Competitor: willing to compete, but requires outside motivation
Survivor: just simply trying to survive his day
"We define that for them, so they can self-identify and correct what they need to correct. That stuff starts happening right away, and the cream starts to rise to the top."
In 16 seasons as a head coach, the 49-year-old Chesney has had one losing season: a 5-6 mark in 2018, his first at Holy Cross. By 2022, the Simmons's Crusaders were undefeated until losing to eventual national champion South Dakota State in the FCS semifinals. He inherits a 3-9 UCLA team that's certain to be more competitive than the 2025 Bruins roster, simply because they won't know any other way.