The Secret Life of a Serial CEO

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But Faucher insists on going through the rest of the slides, albeit with rushed commentary. Cramer, looking a little flushed, prods him sharply to wrap it up. "Next slide…Quick…Go…Finish…" When Faucher mercifully hits the last slide, Cramer turns to the partners and says, "Done. Ask."

The partners want to hear about who else is involved with the company. Cramer doesn't wait for Faucher to answer; he quickly ticks off a few of the luminaries who are advising the company--including Gail Goodman, CEO of the successful e-mail marketing company Constant Contact (NASDAQ:CTCT) (she's the one who introduced Cramer to Faucher), and Don Rose, the founder back in the '80s of the highly regarded record label Rykodisc and a well-known figure in the Boston music scene.

"Let me give you my initial reaction," says Bichara. "This is a great business opportunity. You know what you're doing, you don't have much direct competition, and you have the right advisers. I'd like to take a serious look at investing. But I'd need to hear more about how you'd defend your position and better data about the segmentation of the market."

Outside, Cramer confesses he is surprised and elated to get what he regards as such highly positive feedback right on the spot after their first pitch. But he notes that the clock is ticking for Nimbit. It's just about out of money, and if it doesn't have a term sheet, or tentative agreement with VCs, within a matter of weeks, the company may have to fold. Atlas may be interested, but it has to be pressured into moving quickly. "We absolutely have to get other VCs in the game," he says.

March 13, 2007
Flagship Ventures, Cambridge, Mass.

Cramer is ushered into a corner office with a stunning wraparound view of the Boston skyline climbing up from the Charles River. Jim Matheson, a partner, maneuvers around the golf clubs leaning against the whiteboard to greet Cramer warmly, and the two quickly get down to business. This meeting is one of a series of informal discussions Cramer has arranged with various VCs to explore opportunities for him. At least that was the original plan.

Matheson runs through several start-ups in which Flagship has invested to gauge Cramer's interest. One is an alternative energy effort; another is a media distribution company; even an online music company has made it into the portfolio. Flagship has become especially interested, Matheson says, in start-ups that could help millions of solo entrepreneurs do a better job of business management. Like, for instance, musicians, he says.

"I'm interested in that, too," Cramer says casually. "As a matter of fact, I may have found the right opportunity." He sketches out the idea behind Nimbit. "We're raising money fast." Matheson is quiet for a moment. "Would you run it?" he asks. "Well, there's a CEO right now," says Cramer. "But I'd do whatever it takes to make it fly."

Later, Cramer tells me that Matheson's reaction is typical, and he's worried about whether Nimbit will be able to get investors onboard if he doesn't step in as CEO. "If I go to the VCs and say I'm in love with this company enough to take it over, they'll want to put in $5 million to $12 million," he says. "But if I don't take over, they'll question my commitment. I can try convincing them that I'm committed as executive chairman, but they'll just wonder what I'll do if a great CEO opportunity comes along in six months. And I can't take the reins temporarily from Patrick, get the funding, then give the reins back to him. It will look to the VCs like I want out."

He's interested in being CEO, he says. But he doesn't think Faucher is ready to have what Cramer refers to as the Conversation. He reminds me he has a rule against butting heads with founders. The one time he did it, at a company called Software Emancipation Technology, everyone ended up miserable. The big question, then, is whether Faucher will be ready to relinquish the top title before time runs out.

April 13, 2007
Naked Fish, Framingham, Mass.

Cramer is here at this restaurant to give me an update. Three VC firms are looking into a Nimbit deal: Atlas, North Bridge Venture Partners, and Commonwealth Capital Ventures. A few others are interested. But he wants only two to chip in, so each can get a big enough piece of the company to feel invested. Meanwhile, he has managed to set the clock back a bit by taking in another $200,000 from the angels, raising total funding so far to $1.4 million. "That gives us to the end of June," he says.

And something else: He and Faucher had the Conversation two nights ago. If Nimbit gets venture capital funding, Cramer will become CEO.