Lawyering at warp speed: living the entrepreneurial life

By John Masson

Bob Stefanski learned the importance of speed and sound judgment on the football field. But the Northern Michigan University hall-of-fame receiver didn't fully appreciate the value of the lesson until years later, when he gave up the white shirts and wingtips of Big Law for the blue jeans and sandals of Silicon Valley.

How the 1989 Michigan Law JD went from corporate attorney to entrepreneurial advisor, he says, had more to do with seizing opportunity than any built-in entrepreneurial bent on his own part. But key to his subsequent success—and the success, he says, of any attorney working in the entrepreneurial arena—was his ability to analyze a situation rapidly and get the right advice to the client, right away.

"The kind of guys I'm used to working with, you don't always have time for in-depth analysis," Stefanski said. "It's more like, 'What should I do, and how fast can I do it?' You need to be able to synthesize law, and you need to understand their business really well. Things are moving extremely fast, and very quick judgments have to be made."

Stefanski isn't saying an entrepreneur's lawyer doesn't need to know the law inside and out—far from it.

"You need to know the law extremely well, that's for sure—you can't be a good lawyer without that," he said. "You just don't have the luxury, usually, of all sorts of time for in-depth research."

The Grand Blanc, Mich., native remains actively engaged in his home state, passing on the lessons he's learned to a new generation of entrepreneurs through outlets such as Michigan eLab, co-located in Ann Arbor and Palo Alto, Calif. Although it's partly a business incubator, Michigan eLab is primarily a venture capital fund established by Stefanski and others who have deep ties to U-M's entrepreneurial side.

It hasn't always been so for Stefanski, who also holds a Michigan Engineering graduate degree. He said he was simply following his natural interest in intellectual property and technology to a first job with Weil, Gotshal & Manges in New York.

"When I left Michigan, like most students, I was just focused on getting a job," Stefanski said. "I knew I wanted to do something around technology, and something around intellectual property—but I was not focused on start-ups or entrepreneurship, per se."

While with Weil Gotshal in the early 90s, he represented companies ranging from global behemoths to very small start-ups, and he paid close attention to ongoing developments in the IP and technology fields, which were on the brink of exploding. He also met a succession of high-powered technology executives, learning what he could from each.

It was a little later, when he was corporate counsel and IP chief for Reuters, that he met Vivek Ranadivé, a visionary tech entrepreneur whose innovations had radically changed Wall Street—and who would radically change the course of Stefanski's life.

The tech entrepreneur had started a company called Teknekron, which digitized Wall Street in the early 90s and enabled traders to spend far more time trading stocks, and far less time researching them across stacks of separate computer terminals.

Reuters had acquired Teknekron, and the entrepreneur Ranadivé was figuring out what to do next. Stefanski got involved, and it was decided to spin off a new company, TIBCO Software, which would license the original Teknekron technology and find different markets outside of Wall Street in which to apply it. Stefanski worked with Ranadivé and Reuters in setting up the new company, and Ranadivé asked Stefanski to join his team.

"I wish I could say it was brilliantly planned, but it was an opportunity that no idiot could refuse, to be honest with you," Stefanski said. "It was clear he was a brilliant, brilliant guy."

Stefanski gave up his "very corporate practice" in New York and made the move to California, where as a founding member of the TIBCO management team, he says he worked every bit as hard, although in a less buttoned-up environment.

"Now I did everything—I didn't have a staff. I was going out with the engineers and pitching to customers … really, doing sales. Then I would negotiate the deal and draft the contract, and then I'd sign it," he said. "There was no one else to do it."

In TIBCO's early days, it was all about figuring out what needed to be done to get customers in the door. Nevertheless, Stefanski said it was a mostly trepidation-free process.

"Certainly there was a little angst along the way, but from a personality standpoint I was much more comfortable. I loved it. I loved being an entrepreneur, I loved making it up as we went along."

The angst arose on those occasions when he thought a little too deeply about the financial stability he had left behind with his Big Law job, and the huge amount of competition his infant company faced. At one point he counted 15 serious competitors, and he asked himself one night, "How are we possibly going to differentiate ourselves from these other guys?"

Eventually, they did, and TIBCO became a leader in developing software that helps companies gain a competitive advantage through speedier processing of massive amounts of information.

Which, ironically, more or less describes his own role at TIBCO: processing legal information and acting on it, rapid-fire, within the company.

"For me, the conversations and interactions are more akin to 140 characters on Twitter than to the long memos of big corporate firms," he said. "It's pretty much a full-contact sport, and a super fast-moving sort of practice." ​​​​