Guest also is vice president of South Oak Jeep-Dodge-Chrysler-Ram, the dealership in suburban Chicago that he runs with his father, Dennis. Guest is adjusting to life as a grounded scout while his store makes adjustments of its own by transitioning to selling cars and trucks digitally.
Guest’s scouting responsibilities typically shift into overdrive from February through the summer, when he would check out top college players in talent hotbeds such as the Cape Cod Baseball League, which was canceled this year. With his new schedule, Guest said he’s enjoying the extra time at home with his wife and three kids.
“You do feel like a part of you is missing,” Guest, 37, told Automotive News in late April as life without baseball sank in. “As far back as I can remember, on this particular day, right now, there’s baseball being played somewhere and I’m watching it, or playing it or doing something with baseball at this time of year every night, and that’s just gone right now.”
Growing up, Guest had no intention of joining the family business. He did what he could to help out during the summers, working as a porter or in other jobs, but didn’t pay much attention to that world. His passion was baseball.
Little did he know that the sport he loved eventually would bring him back home.
He went from a youngster who tagged along to White Sox games with his season-ticketholder father to a college player good enough to be drafted by the White Sox in 2004 after stints at Purdue University and Saint Joseph’s College in Indiana.
He played in the club’s minor league system as an infielder for three years, but Guest felt his talent had carried him as far as it could. So while he was still playing, he began setting up his next career.
Guest would sit near the coaches in the dugout during games to see how they thought through certain situations. He picked their brains when possible.
He was released by the White Sox in November 2006 but wasn’t out of the game for long. The Detroit Tigers hired him the following February for $500 a month as a baseball operations intern, before putting him into scouting and developmental roles the next year. He had a homecoming in fall 2009, returning to Chicago as the Tigers’ Midwest scout.
Guest’s father asked him to come help out wherever he could. Dennis Guest was looking for a fresh perspective, so Garrett, who didn’t know much about the industry at the time, began immersing himself in dealership life while pulling double duty with the Tigers.
He’d do his scouting reports and interviews each day, then stroll through the dealership and ask staffers about the operations. He raised questions about why certain processes were handled the way they were and sometimes was told that’s just how the dealership always did it. The answer didn’t sit well with Guest, especially with the economy still shaky after the Great Recession.
“I literally was introduced to the business at the worst possible moment,” he said, and with such little room for error, he looked for ways to make the dealership more efficient.
“I just started making notes for myself and eventually we got to the point where it got really, really tight and got really, really scary for a while,” he recalled.
Advertising was one area that needed updating. Guest said the dealership was too reliant on newspaper ads and needed to shift resources to the digital realm through Google and social media. He ran this game plan by his father, who was hesitant at first.
“It was really, really hard for him to let go of his instincts a little bit and maybe get pulled in a different direction, but to his credit, he did it,” Guest said.
After a few years of working for free, Guest took a leadership role at the store. While he moved up at the dealership, he also switched baseball teams, jumping to the White Sox in 2014.
He became Chicago’s assistant scouting director last year.
The dealership has continued making progress to keep up with the times. Amid the pandemic, the store rolled out FCA’s new Online Retail Experience platform and has been delivering vehicles directly to consumers.
With so much on his plate, there are times when Guest’s phone rings and dinner gets cut short. The nature of both jobs means “there’s no real flow or schedule to it,” he said.
But he has been able to keep the two careers from overlapping. “I find that the advantage of taking a 24/7 mindset,” he said, “is, [even though] it sounds crazy, you can kind of space things out enough to where they don’t ever intersect.”