An opportunist who made his won luck

PEARLSTEIN: Michael Chasen is ending his tenure with Blackboard Inc., a provider of course management software to colleges and universities. (Blackboard Inc)

Michael Chasen loves to tell the story of the day he and his roommate from American University, Matthew Pittinsky, left their jobs as education consultants at KPMG's Washington office to launch a technology company in 1997.

Their boss, aware that the 22-year-old entrepreneurs were strapped for cash, told them they could take their desktop computers with them. So on the last day, they loaded the bulky computers onto their rolling desk chairs and headed downstairs.

The guards in the lobby were naturally suspicious and demanded some authorization for removing the computers from the building. Chasen pulled out a letter from his boss, and the guards duly made a copy of it, along with a copy of their drivers' licenses. They also took care to write down the serial numbers of the monitors and processing units. Then, with all the paperwork complete, they headed out the door.

"Of course, what we were really doing was stealing the chairs," Chasen confesses.

Chasen tells the story with the perfect setup and timing of the standup comic he might have been if he hadn't founded Blackboard and grown it into one of the world's dominant providers of course management software to colleges and universities, with more than $600 million in revenue, 3,000 employees and a market value of about $2 billion. Anyone who's been a student or teacher (like me) at a college in the past decade knows Blackboard.

But sometime in the next few weeks, Chasen will walk out of Blackboard's headquarters for the last time, having sold the company to a private-equity firm for $1.8 billion. As usually happens in such circumstances, after a one-year transition, he is now stepping down as chief executive.

Blackboard is one of Washington's most remarkable business success stories, all the more so since it has nothing to do with the federal government. And by all accounts, much of the success is because of Chasen, a force of nature who combined hard work and wily determination with an uncanny knack for getting investors, employees and customers to follow his lead.

As the story of the chair illustrates, Chasen is one of those opportunists who manages to create his own luck, a geek whose entrepreneurial bent was already evident when he began charging $25 an hour while still in junior high school to write programs on his father's Radio Shack computer for small businesses in his hometown of Cheshire, Conn.

While in college, he managed to snare a rare part-time job doing tech support at the FBI. And after spending hours filling out applications for law school and business school, he came up with a program for online applications that he and Pittinsky tried to peddle to U.S. News and World Report, the Princeton Review and several universities. They all said it would never fly.

One of Blackboard's early backers was Novak Biddle Venture Partners. Roger Novak admits to turning down Chasen's first proposal because of his lack of experience both with business and software programming. He changed his mind six months later after Chasen and Pittinsky teamed up with a rival group of programmers from Cornell that had already developed a crude course-management program.

Blackboard is one of the few startups from that era to survive the bursting of the dot-com bubble. Chasen and Pittinsky resisted the lure of taking the company public and never fell into the trap of chasing eyeballs rather than revenue. By the time the bubble burst, the small company was already breaking even and had attracted $100 million in private investment from a group that included Washington's Carlyle Group and Kaplan, a subsidiary of The Washington Post Co.

"We used to joke that anyone can be smart and successful — it's when you're dumb and successful like we were back then that is the mark of true genius," recalls Pittinsky of those early days.

Once the dust from the dot.com bust had cleared, Blackboard used its cash stash to buy up any upstart competitors. This aggressive acquisition campaign, which received no resistance from Bush-era antitrust regulators, culminated in its 2005 purchase of Canada's WebCt, giving Blackboard a 70 percent share of the fast-growing market for Web-based course management systems.

"We knew that if we could get scale quickly and sign up 300 schools, we'd become the IBM of the industry," Novak told me last week. As with the old IBM, Blackboard became the default choice for any IT director not wanting to stake his career on choosing an upstart competitor offering a cheaper, better but unproven alternative. Then, once a school had signed up, the hassle involved in switching to a new system created a strong incentive to renew its Blackboard contract.

A few years back, a new set of rivals began gaining market share by offering cheaper and more flexible alternatives based on free open-source software known as Moodle. Blackboard responded with a patent suit that seemed like bullying to many in the more genteel world of nonprofit higher education. But as the suit dragged on and the company's market share fell toward 50 percent, Chasen pulled out his old playbook and began acquiring some of its open-source competitors, including Baltimore-based Moodlerooms. As a result, Blackboard is now the largest supplier of open-source course management software as well.

Novak, who has seen his share of entrepreneurial failures as well as successes, marvels at the way Chasen was able to mature as his company grew, avoiding all of the usual potholes into which company founders often fall.

Early on, he and Pittinsky agreed to hire an experienced chief executive until the pair of young founders had enough experience to take the reins: Pittinsky as chairman with primary responsibility for dealing with investors and customers, Chasen as chief executive focusing on operations.

When it was time to take the company public in 2004, there was some concern that Chasen's direct, hard-charging leadership style might not sit well with Wall Street. With prodding from Novak and the board, Chasen smoothed some of his rough edges, learning to listen better and delegating more.

In many startups, the early camaraderie of the original founders and initial employees gives way to jealousy and rivalry. Not at Blackboard. Many of the original Cornell programmers are said to have left on friendly terms to start their own companies, in several instances with investments from Chasen. And in 2008, Pittinsky decided to give up his executive duties and pursue a long-delayed academic career while remaining a Blackboard director and close Chasen friend.

Even the sale of the company to Providence Equity Partners last year has managed to avoid the usual rancor between entrepreneurial founder and his new bosses. The hiring of a new chief executive, Jay Bhatt, is a reflection of Providence's desire to combine Blackboard with another of its holdings and take the combined company to the next level. It also reflects Chasen's desire, at 41, to throttle back after 15 years of 80 hour weeks to spend more time with his wife and three young children at home. With an investment bubble developing in the education technology space, maybe Chasen also sensed that it was a good time to get out.

Although he a millionaire many times over — his compensation in 2010 topped $3 million and his proceeds from the sale to Providence exceed $20 million — Chasen keeps a low profile. He's not active in politics or the charity circuit, doesn't have any vacation homes, doesn't play golf or collect art or serve on nonprofit boards. His one indulgence seems to be a motorboat he uses to take the kids out on the Potomac River.

A boyish 41, Chasen is now one of the elder statesmen of the tech community in Washington, a status confirmed by his invitation to address one of the Titans of Technology mega-breakfasts last week. He expects to continue doing angel investing while looking for some other enterprise to build and grow. He is full of pride and satisfaction with the company he built and still marvels at how lucky he is to have been able to realize his boyhood dream of growing up to run a computer company.

"What's it like to be giving up your baby?" I asked him last week as he sat in a temporary, windowless office across from his old suite. The stolen desk chair, which he has used ever since, had already been moved to his office at home.

"It's not my baby anymore," he replied somewhat wistfully, "It's my 25-year-old, and it's time for him to move out of the house."