Any regret over losing a job with Donald Trump to competitor Bill Rancic was quickly salved by a rush of offers and by Jackson's own ambitions to make the most of his reality TV fame.
"This was basically a chance to have NBC pay for a 15-episode Kwame commercial in a business environment," Jackson said of "The Apprentice."
In a phone interview from New York, Jackson said he is weighing offers from another famous billionaire, Mark Cuban, as well as the KFC fast-food chain. He's also starting his own company.
Being No. 2 is turning out to be as much a problem for Jackson as it was for "American Idol" runner-up Clay Aiken, who has outsold winner Ruben Studdard.
"My theme is, 'Don't cry for me, Argentina," said Jackson, 30, a Wall Street investment manager before "The Apprentice."
Even the antics of Omarosa Manigault-Stallworth, whose scheming may have cost Jackson the top prize - a $250,000, yearlong job with Trump - is something he shrugs off.
"I have moved on, and every new endorsement deal makes me happy," he said.
During Jackson's final "Apprentice" test, staging a concert with Jessica Simpson, Manigault-Stallworth flubbed transportation for the pop singer and appeared to fib about it.
Does Jackson think she lied to him?
"There's no 'think' about it. It's 100 percent on the tape. There's no need to think about it. It's like watching Rodney King get beat: How did the bruise happen?" he said.
Jackson is starting an entertainment company, Legacy Communications Group, to produce films, video games and live events with a focus on concert series.
"Something I think people don't realize about contestants on the show is that we are true business people, we're not reality show 'Hey, I'm happy to be on camera' people," he said. "We're people who are focused on the bottom line and commercializing this opportunity."
One of the first Legacy projects: helping raise $2.5 million for a documentary on Florida State football coach Bobby Bowden, a project by filmmaker George Butler ("Pumping Iron" with Arnold Schwarzenegger).
Jackson is working with longtime friend Dave Smith, who encouraged him to use television as a means to the end of business success.
"When he first presented the idea to go on the show he sent me a note saying this could be a big opportunity for us to be like Matt Damon and Ben Affleck," who used their success with "Good Will Hunting" as a platform for other projects, Jackson said.
The offer from Cuban involves handling an investment portfolio and working on operations for the Dallas Mavericks, the basketball team owned by Cuban, according to Jackson.
The KFC deal, reported to be $25,000 weekly for his endorsement of new menu items, needs a bit of seasoning.
"It's not because of the $25,000. I'm not really up for a publicity stunt. I'm more focused on, `If you want to do a true endorsement deal, treat me like a businessman and let's do it,"' he said.
If he had bested Rancic, Jackson says he would also have picked the chance to oversee a 90-story building project in Chicago over managing a Trump-owned California golf course.
"If you can look back at a city skyline and say 10 years from now, 'I redefined that,' that's a lifetime legacy and I think it's great for Bill," he said.
And what will people connect to Jackson a decade from now?
"A tropical drink, a tropical island, a happy man. That's what it's about, living well," he said.
By Lynn Elber