It would be hard work, require long hours and certainly test his volatile temperament. It could interfere with his driving, expose him to failure and make this first season the most difficult of his decorated career.
Not so much.
Three months into the season, Stewart looks like a genius. Using an extreme makeover on the former Haas CNC Racing organization, Stewart has put together one of the most solid organizations in the Sprint Cup Series and made other drivers believe ownership might actually work.
He's currently third in the standings, and after a rocky start to the season, teammate Ryan Newman has vaulted 23 spots over the past seven races to 10th in the points. They finished second and fourth, respectively, Saturday night at Richmond and both are currently in contention for berths in the Chase for the Sprint Cup championship.
"It's been impressive to watch the change, the mentality that Tony has brought in there about not being there just to be there, but to be there to win," rival driver Jeff Burton said. "I'm not sure I remember a team changing possession, a new owner stepping in, and the turnaround being what it's been.
"He's making other people want to go and own their own cars."
It was just over a year ago that Stewart first admitted he was looking at opportunities outside of JGR, his home for all 10 years of his Cup career. He had a year left on his contract, and team owner Joe Gibbs was eager to lock the two-time series champion into an extension that would keep him in the No. 20 until Stewart retired.
Knowing Gibbs was working on an offer, outside suitors stepped in to urge him to listen to other opportunities. One was a 50 percent ownership of Haas, a rudderless organization since Gene Haas' 2007 conviction on tax evasion charges.
To the disbelief of many, Stewart's interest was piqued. He deftly negotiated an early release from his Gibbs contract, then finished the paperwork that gave him control of renamed Stewart-Haas Racing.
Still, the team didn't have much to show for its first seven years at NASCAR's top level. Just one top-10 finish in 284 starts for 12 different drivers, spotty sponsorship and an alliance with mighty Hendrick Motorsports that had yet to work to the team's advantage.
Stewart wasted little time putting his stamp all over his new toy. He courted sponsors, hired his own people and changed the mentality to mirror his competitive spirit. Even so, it seemed a stretch that the transformation would lead to immediate success. Maybe someday, but certainly not the first year.
Again, he's proved otherwise. Stewart has seven top-10s in 10 races, including runner-up finishes in two of the last three races. He lost to Mark Martin three weeks ago in Phoenix, and Kyle Busch on Saturday night in Richmond.
Although he's yet to grab a win this season, he's thrilled with his performance.
"I told somebody that I would rather have five second-place finishes in a row than I would have a win, a 32nd, an 18th, a 43rd and a seventh," he said. "That consistency and that momentum of being up front every week and knowing that you have an opportunity to run for the win each night, that's what carries you into that week-after-week stretch."
SHR has also been buoyed by Newman's turnaround. He was 32nd in the standings following the fourth race of the season, his fourth finish of 22nd or worse. But his crew regrouped during the bye week and has been on a roll ever since.
Newman has not finished lower than 16th since, and had consecutive top-five finishes at Talladega and Richmond for the first time in longer than he could remember.
"We got two cars in the top five, which was a first for us, and hopefully it's a first of many," he said. "It's been a long time for me with two straight top fives."
The strong runs have Stewart-Haas Racing far ahead of schedule and exceeding the modest expectations most people placed on the team.
"Momentum's everything. That gives you such a head start when you get to the next track," Stewart said. "For us as an organization, with that momentum, I can't wait to get to the shop Monday and see the smiles on the guys' faces. That's the payoff for me. That's the stuff that will carry us into Darlington next week and carry us into the All-Star Race the week after that."