For the last 11 years, Jacob Doss has built the Windermere Prep football program from the ground up. Now, he is stepping away and taking on a new era in his life.
| 12:25 p.m. December 9, 2020
When Jacob Doss stepped off the football field following Windermere Prep’s 14-13 win over Legacy Charter, he knew he was going to get one more game.
Or at least, that’s what he thought.
That night — Friday, Nov. 6 — Doss was enjoying his team’s hard-fought win while looking toward the following week’s playoff game against Bishop McLaughlin. He was expecting a tough game, but what he wasn’t expecting was for that cool night at Ocoee Bulldog Field to be his last in Laker red and blue.
“I was not ready for the season (to end),” Doss said. “We were walking to practice when we got the word that half of our team was going to be quarantined. That’s when it hit in — because we’re in playoffs, if you don’t play that game, you’re done. So right there it hit me that, ‘Oh my gosh, I’ve coached my last game at Windermere Prep.’
“That’s why it was so heartbreaking for the kids — for me to share it with the kids that, ‘Hey, our season is over,’ and then a week later, I told them I’m not coming back,” he said. “So they had a double-whammy in a week, which was really tough for me to put on those kids. But at the same time, I say it all the time to these kids, ‘You guys are football players; there is no news that can break you.’”
After 11 years of leading the program since its birth, Doss knew he needed something new to do, and the time to do it was now.
In addition to coaching football, Doss has a degree in finance from the University of Wyoming — where the Kentucky native also played on the football team — and now is working remotely as the director of partnerships at Mia Share Inc., a tech startup based in Jackson Hole, Wyoming, that helps students find the financial means to go to school.
“I’m at that point in my career where I can go all-in coaching or try something new for a little bit and see what happens, and see if I like it and if it’s something I’m interested in,” Doss said. “Football isn’t going anywhere — football is going to be here — and I can always jump back into it, but I don’t know if I can always jump back in going into what my degree was in.”
Doss remembers the moment when the reality of being a football coach hit.
It was 2009, and at age 23, he was standing in front of parents and players at a parent interest meeting after he was hired by Athletic Director Danny Haney. Haney had served as Doss’ high school athletic director. To add to the moment, Doss wasn’t just coaching a football program — he was helping bring one to life.
“I grew up with these boys; I grew up with this program,” Doss said. “And then a year later, I met my wife — she was a teacher at the school — and we just kind of went all-in with building this program. And obviously, I hired a staff, and those guys were with me forever, and the administration couldn’t be more supportive.”
For Doss, meeting his wife, Jessica, was the biggest highlight moment of his many years at Windermere Prep, and the National Signing Day events always rank among his favorite. On the field, fewer moments stand out more than that first game — and first win — all those years ago.
“I had tears in my eyes, and it was crazy,” Doss said. “I played at The Swamp in my sophomore year of college — played in front of 90,000 people — and I was more nervous for that first game that we played at Peniel Baptist in Palatka. … I think there were 25 people at that game, but I was more nervous for that.”
Since then, Doss has coached more than 100 games for the Lakers — and for a time served as the athletic director — and has collected many wins throughout the years. And it didn’t take long for that success to kick for his budding program. In 2014, the Lakers went a perfect 10-0 and won the Sunshine State Athletic Conference. They followed that with 10-win seasons in 2016 and 2017, as well as a 9-1 season in 2018.
A NEW ERA
Doss is excited for the change. He gets to spend more time with his young son, Jackson, as well as Jessica, who is pregnant with their second child.
But just because Doss is no longer in football doesn’t mean it is far from his mind. The others at Mia Share Inc. have caught on to the football metaphor speak Doss often utilizes during meetings and conversation. It’s something he just can’t not do, Doss said.
It’s also why, despite no longer leading the program, there is a good chance if you make it out to a Lakers football game in the future, you will find Doss in the stands cheering on the program that has long been part of his extended family.
“Now, I get the chance to see my boys play,” Doss said. “I told them I’m going to be the biggest fan — I’m going to be the loudest one at the games next year when I watch them. Whoever the new head coach is is just coming into an awesome program. I’m still going to be involved in their lives — I told them, ‘Whether you want me or not, I’m still going to be there.’”