JERRY GLEESON, THE JOURNAL NEWS
(Original publication: November 19, 2004)
Jackson has a pricey retail and residential development project
in the works in Maryland, and ambitious plans for a retail
apparel line and a
television network production deal. But none of it would have
happened if not for the insistence of his pal Dave Smith several
As Jackson recounted the tale at the eighth annual Awards
and Scholarship Dinner of the African-American Chamber of
Commerce of Westchester and Rockland Counties at the Hilton
Rye Town last night, his friend had heard that a new reality
TV show was in the works. It involved Donald Trump and entrepreneurship.
out, Smith suggested.
Jackson, a Harvard MBA, was busy at the time managing investments
at Goldman Sachs. Life wasn't great on Wall Street at the
time, given the collapse of the technology bubble. And Jackson,
who lived in a studio apartment where his bed
abutted the oven, decided to take a little risk.
He and Smith wrangled a meeting with the casting director
for the show.
"We know there is a one-black-guy rule in reality TV.
We brought two, so you could pick one," Jackson recalled
telling the director. They hit it off.
Jackson found himself on the show, "The Apprentice."
It drew tens of millions of viewers. He became runner-up in
the program's contest for which the prize was a job with Trump,
but his life worked out better in other ways.
As Jackson told the audience, he figured the maximum downside
was going back to
work on Wall Street.
"The maximum upside was being here tonight, addressing
you," he said.
Jackson received all sorts of job offers following the end
of the show, but he decided to take another risk by forming
his own company, Legacy Development Partners LLC. The attraction
of a Wall Street paycheck had waned. Jackson, whom
the African-American chamber has named Business Leader of
the Year, said the
recognitions the chamber awarded spoke to something bigger.
"Tonight is about betting on yourself," he said.
Reach Jerry Gleeson at firstname.lastname@example.org or 914-694-5026.Reach
Jerry Gleeson at email@example.com or 914-694-5026.