Before coming to Russia, Jacobson was doing deals in Iraq and Kuwait.
"There's an old Iranian saying", he says, explaining his predilection for chaotic places, "that you catch more fish in muddy water then you do in clear water".
While the going has certainly been muddy for Jacobson here in Russia, he has managed to reel in more than his share of fish.
The 37-year-old Canadian, once an IBM executive, has opened the first General Motors dealership in Moscow under the name Trinity Motors. By mid-October, Jacobson plans to open a Moscow GM service center and a dealership in St. Petersburg. A Kiev GM dealership is scheduled for November.
"The showrooms are under renovation right now, and there's reasons why they shouldn't open on time", Jacobson said.
He also plans dealerships in Alma-Ata and Baku.
But right now, the dealerships are the smallest part of his business ventures. Under another company name, The West Group, Jacobson is building a new stainless steel factory in Aktyubinsk, Kazakhstan, and has begun a $1 billion renovation of a steel mill in the Siberian town of Zlatoust.
The mill, located about 1, 500 kilometers east of Moscow in the Chelyabinsk region, is Russia's largest specialty steel factory.
Jacobson has been working on the project for over a year, taking the bumpy and dangerous drive from the Chelyabinsk airport to Zlatoust more than 10 times. His briefcase is still bloody from the time his van skidded off the road and one of his colleagues was injured.
But Jacobson, a driven dealmaker with a sense of humor, has pursued the project, through uncounted delays and difficulties teaching capitalism to the Russian plant managers.
He credits his success in being chosen for the project from among three larger competitors with his more encompassing business plan, which includes hiring sociology experts from Columbia University to deal with displaced workers.
When the renovation is complete, the plant's production will be the same but its employment will fall from 15, 000 to 3, 000 workers. The project will be paid for using steel exported from the factory and credits from equipment manufacturers.
"There are a lot of people that just want to take things out of Russia", Jacobson said. "Our plan includes a profit for us, but we're also putting back in to the country".
Among his first jobs after leaving IBM was consulting on construction of an automobile factory in Iraq.
"I got part of the contract to do that and suddenly everything went to hell in a hand basket", he said.
Moscow has not been an easy ride for Jacobson, either. He received the rights to an old mansion in the center of the city's center only to learn that Moscow's former mayor, Gavriil Popov, wanted it back. He won the case in court but arrived at work one day to find the doors locked and the building filled with security guards.
Jacobson called in a force of his own guards and a peaceful showdown ensued.
"Our guys were bigger then their guys", he said, "so they went away and we won".
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