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The Secret Life of a Serial CEO

Bob Cramer has piloted six companies to big paydays. Now he has found a start-up that offers something else--excitement, poetry, a legacy.
HOW TREO, WILL TRAVEL: After selling his company, Bob Cramer was flooded with calls from VCs.

Chris Buck

WHAT'S NEXT: Cramer started entertaining offers from a New York-based software start-up.

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October 31, 2006
Papa Razzi Restaurant, Wayland, Mass

Coming in out of the light drizzle to this pop-tony restaurant in this swell Boston suburb, Bob Cramer looks like a man whose burdens do not include doubt, regret, or second-guessing. He is both energetic and at ease, confident and engaging. He occasionally checks the incoming messages on his Treo in an offhand way, as if he's doing so not out of need or concern, but rather out of mild curiosity and vestigial habit. He is trim and looks younger than his 48 years. He's dressed in a blazer over designer T-shirt and jeans--like a man who could afford to be in a $2,000 suit but wouldn't be caught dead in one.

He's here to explain to me what it's like to be a serial high-tech CEO between fast-growth companies, and what he plans to do following the success of LiveVault. Cramer brought that online data-storage company to $20 million in sales; in December 2005, the company was acquired by Iron Mountain (NYSE:IRM) for more than $50 million. Cramer made a bundle on the deal and believes he could have made perhaps twice as much if the founders had followed his advice to hold off on selling while the company was still growing like crazy. But he dismisses the hypothetical lost millions with a wave and a smile. He's plenty well-off. "I don't have to work," he says. "I can live off the interest."

At the moment, he is being courted by a small horde of top VCs who are intimately familiar with his string of successes--which dates back to Oracle Software, where he was a key sales executive during that company's legendary explosive growth, and runs through several other software companies, the last three of which he ran as CEO. "I've never had a failure," he says. The VCs began calling right after LiveVault was sold. But Cramer told them to give him some space for a year. He wanted to spend more time with his wife and young children. He wanted to reconnect with two of his passions, painting and music--he played in a band as a kid; now he practices in a small studio he's put together in his basement. He travels to Mississippi to help build houses for victims of Hurricane Katrina. He and his wife take in foster children. And right now, he's not quite ready to give all that up to go full bore into company-hunting mode. "Exploring opportunities can make you busier than a full-time job," he says.

Still, he recently started taking calls from select VCs, just to get a sense of what's out there. Nothing seems seriously tempting. "I have an offer to run a data-storage company," he says. "Maybe I'll think about it if I can't find anything else." In the meantime, he's networking with a group of CEOs that meets once a quarter or so. And he's advising a couple of small companies. One consists of a few guys who want to take a new approach to producing video advertising for the Internet. Another is a music start-up that lets independent bands manage themselves online. Though neither seems like the kind of high-powered opportunity he's looking for, he appreciates the chance to combine business with his artistic side. Cramer's degrees were in engineering, he cut his teeth at Bell Labs, and his companies have all been hard-core software ventures. But now he's thinking that when he does finally pounce, it just might be on a start-up with a little more poetry to it than offline storage or database software. "I'd love to find something that I can personally relate to," he says.

Perhaps that's being a bit fanciful, he concedes. But when it does finally come to taking the reins of a company, he's developed certain rules and constraints that he won't compromise. For example, he doesn't want to create a company from scratch; he wants to take over a start-up that a founder has already piloted against all odds to real promise. Another rule: When you take over, take over. "You have to step in and assert immediate control, even if others in the company aren't ready to accept a new leader," Cramer says. At the same time, he adds, you have to find a way to win over people, especially the founder, without bludgeoning them. And finally, he wants a company that can attract customers virally on the Web--that is, by finding a way to get Internet users to spread the word to one another. LiveVault hit it big, he notes, after he ordered up a funny video, starring John Cleese, that was downloaded some 300,000 times. "If you can't pull something like that off, then your cost of customer acquisition will kill your margins," he says.

Meanwhile, he says, glancing absently at his Treo, there is no need to rush to try to find the perfect company. He seems to have no idea that it has already found him.

Febuary 26, 2007
Starbucks, Wayland, Mass.

Four months later, Cramer seems a little different than I remember him. He appears a bit sharper-edged, a little faster to pull out his Treo. He's speaking more quickly. Maybe it's just the coffee.

He explains that he stopped taking calls about CEO opportunities shortly after our last meeting. "It's like looking for a house," he says. "After a month, you've seen everything promising on the market, and there's no point in looking anymore." But he recently started looking again. There's a biodiesel start-up that looks interesting, but he's made a decision: He doesn't want to settle for something interesting. He's determined to build the Next Big Thing online.

Any promising prospects? As a matter of fact, he knows one outfit that might come close, though it's not one he intends to run. He recently joined the board of that band-management start-up, which is called Nimbit. The real money in the music business, he points out, has traditionally been in high-profile bands that are promoted by major record labels. But now that music is freely sold, bought, and shared on the Web, artists don't necessarily need the big-money backing of a label. They can do nearly everything themselves online--and make more money because they get to keep most of it. As a result, the money flowing to independent bands is expected to grow from about 20 percent of music industry revenue to more than half; indie music is already a $16 billion market, he says. There are plenty of online sites that help independent musicians sell MP3s, and sites that sell CDs, and sites that sell merchandise, and sites that sell tickets to concerts, making for a heavily fragmented industry. What's missing is a service that coordinates and monitors all of these activities. That's Nimbit. "I love the vision," he says. "And it addresses that artistic side of me."

The investors want him to be CEO, he says, but he has accepted only the title of executive chairman. "I want to mentor the young guy who's the CEO-founder and help the company get funded," he says. "I'm just giving them two to three days a week of my time. That leaves me time to paint and play music."

As it turns out, he and the Nimbit team are planning to meet the day after tomorrow to go over the presentation for the company's first pitch to VCs, scheduled in two weeks. "They already have a million in angel funding, but I don't like angel funding," Cramer says. "Angels are for small ideas. They need VC money." But the team needs to gird for battle, he adds: "Boston VCs don't get the music business. And the process of raising VC money is all about making entrepreneurs jump through hoops. That's how they learn about you. They want to see what kind of stick-to-it-iveness you've got."

But he knows how to work the VC process, he notes, and he has faith in it, just as the VCs have a lot of faith in him. "When they say no, there's a good reason," he says.

Febuary 28, 2007
Nimbit Headquarters, Framingham, Mass.

Nimbit's office is too far outside Boston's high-tech Route 128 belt to be considered part of it. Indeed, the neighborhood is a bit seedy, the building is dingy, and the offices are cramped and helter-skelter. Scattered among the mismatched chairs in what serves as a conference room is the Nimbit team. Cramer is running the show; it's his laptop connected to the projector. Next to him is Patrick Faucher, CEO and co-founder, whose long wavy hair, facial stubble, and hip eyewear all nicely accent the grungy cherubic looks of a former boy bander. Though Faucher did in fact do a fair amount of gigging back in the day as a trumpeter, his background is mostly in software and e-commerce; he previously developed and sold an online shopping site. Across the table is COO and co-founder Phil Antoniades, an impressively biceped, unsmiling, and generally rough-edged-looking fellow whom you could easily picture climbing off a hog to administer a beating to someone like Faucher just on principle. Antoniades was a touring drummer who for a time averaged 200 nights a year on the road before he built up a band management business and then a $1 million CD replication company that he merged into Nimbit. (And despite his appearance, he turns out to be perfectly civil, if a little intense.) Cramer is again dressed in blazer, T-shirt, and jeans. Others in the room include Robyn Glaser, a former executive at EMI who heads marketing at Nimbit, and Bill Snapper, who by all accounts is a genuine website-coding magician.

Faucher has put together a PowerPoint presentation, which Cramer is critiquing. Cramer tries to tease enlightenment out of Faucher through a sort of Socratic dialogue rather than just telling him what to do, but it's hard to miss the fact that Cramer thinks there's a lot Faucher doesn't understand. Cramer fires off questions relentlessly: "Do we need all these screen stats?" (VCs see a lot of presentations, he notes, so the way to get them to remember yours is to keep it uncluttered and repeat key images.) "Is this slide showing the product as it is now or as it's going to be?" (It actually can hurt you to try to make your existing product look too good, because the VCs will wonder why you haven't hit it big yet if your product is so great.) "How are you going to be noticed with all the other players out there?" (Faucher says there isn't a one-line answer to that question, and Cramer tells him to get one.)

The slides drag on; there are 25 of them. Cramer wants the presentation cut to no more than 15. Faucher seems exasperated. "I've barely slept in three days, and not just because I have a new baby," he finally blurts out.

Cramer suggests they wrap it up, telling Faucher not to worry. "In this A round of financing, VCs want to see you've got a great idea that's unique and defensible, and a good team," he says. "You'll figure all the rest out for the B round." He tells Faucher to think big. "VCs aren't like angels. They're not thinking about how they can make $500,000. They're thinking about how they can build a billion-dollar business. Don't refer to exit opportunities--think next major media company; think replacing the labels."

As the group leaves the room, bound for a late lunch at a nearby Brazilian restaurant, Cramer grabs three coffee mugs and takes them to a sink to wash them. "Hey, it's a start-up," he says.

March 12, 2007
Atlas Venture, Waltham, Mass.

Atlas is situated in a warren of high-tech VC firms huddled together behind a snazzy glass façade in a bucolic setting. These are pricey digs, and Faucher has cleaned up a bit for the occasion, looking more Hollywood than grunge today. Antoniades, meanwhile, looks even more menacing. They're both nervous. Cramer, on the other hand, seems in his element as he chats up the two executives who have come to the conference room to hear the pitch.

Faucher gets less than a minute into it before partner Axel Bichara starts interrupting. "Your metrics are unclear," he snaps, gesturing at a slide that shows how the music market breaks down into labels and independent artists. "What are you measuring? Sales? Units? You have to understand segmentation if you're going to be in a long-tail market." Antoniades responds that revenue figures for independent musicians are conservative because they don't include gigging. Bichara fires back: "Well, what are the gigging revenues?" Faucher and Antoniades stare blankly. Cramer, who has clearly been at pains to try to stay in the background, jumps in to assure Bichara that gigging will be integrated into the Nimbit system and carefully tracked.

Eventually Faucher seems to find his footing, and the Atlas partners appear to be taking in the pitch with interest. Peter Shannon, an Atlas associate, asks about the competition, whose names he can rattle off without glancing at notes: Indie911, Snocap, CD Baby, Echomusic, GigShare.

Faucher maintains they're not really competitors, because Nimbit will actually help musicians sell at all these sites, even updating the listings there automatically.

"Will you be competing with iTunes?" Bichara asks.

"iTunes is becoming like a major label," says Antoniades, with what seems like heartfelt scorn. "They're doing the same things to independent musicians that labels did. They're making musicians pay for exposure." Faucher adds that while Nimbit will help artists place their songs on iTunes, it will advise the artists to try to shift sales away from iTunes to avoid Apple's (NASDAQ:AAPL) cut, which can be as high as 50 percent.

The partners both nod, impressed. Sensing the upswing in interest, Faucher goes all-in. He jumps to a slide showing revenue projections, waits a beat, lowers his voice, and says, "This could be a billion-dollar business."

If the partners doubt it, they aren't showing it. In fact, they briefly take over the pitch themselves. "What we're really looking for in a company like this is a network effect," Bichara says. He apparently means viral marketing. He wants to know if there is some way that interest in Nimbit can be made to cascade online, so that musicians end up recruiting other musicians. In other words, will Nimbit have to market hard to win over bands one by one, or is there a way to get it to catch on instantly with tens of thousands of bands?

But Faucher either doesn't understand the comment or chooses to ignore it. He continues on with the next slide.

Shannon persists: "Where's the network effect?"

Faucher stammers. Antoniades shrugs. Cramer speaks up. "We could give you 10 different answers to that question off the top of our heads, but we really need to think that through," he says. Both partners look at their watches. "We're just about out of time," says Bichara.

"I can finish if you just give me two uninterrupted minutes," says Faucher peevishly. Cramer flinches. The point of the presentation is to engage the partners, not to force them to stare mutely at a parade of charts and bullet points.

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.

He couldn't wait any longer, he says. "Every one of the VCs has asked me if I'd take the CEO role if necessary." The message to him was clear: A deal wasn't likely without him as CEO. Meanwhile, he had been stuck in limbo, not really in charge of the company but forced by his commitment to Nimbit to turn down the CEO offers that were coming his way.

The talk was difficult. "Patrick still has to get his arms around it," he says. "Until now, it's been about how I can help him be CEO, not about taking it from him." Cramer wants Faucher to start focusing on forging partnerships with other music sites and to be one of the company's spokesmen. Faucher is mulling it over.

In spite of the tension, Cramer says he feels relieved to have the decision out of the way. But he's also worried that he may have made a mistake in waiting so long to take over. "I could have executed on funding much better if I had taken over as CEO earlier," he says. "We needed to be driving the discussion with VCs, but they've been driving it. That could be hard to fix."

May 9, 2007
Starbucks, Waland, Mass.

Cramer has some good news. North Bridge and Commonwealth seem inclined to partner and go ahead with a deal. They've scheduled a joint due diligence meeting for two weeks from now. If all goes well, the meeting should lead to a term sheet.

But Cramer seems a bit anxious and subdued. He'd prefer to be fielding at least a few more potential deals, but half a dozen other firms have passed. Cramer is suddenly talking like a man who could use a time machine. "If I had gone in in the beginning to the VCs and said this was my deal, all their concerns would have been addressed," he says. "All my CEO friends said I should take over right away." He pauses. "But if I had forced things that way, it would have undermined the relationship. Or maybe I hesitated because I had doubts about Nimbit. I don't know. You can always look back and ask yourself what you could have done differently."

But Cramer intends to ace the North Bridge-Commonwealth meeting. To that end, he has tweaked Nimbit's business model. To differentiate the company from the growing ranks of sites aimed at independent musicians, he has decided to target band managers. Where other websites focus on linking musicians to their fans, Nimbit will focus on linking band managers to these other sites--and to back-end services like mining fan databases and tracking revenue. And forget viral marketing designed to pull in hordes of musicians who might contribute a few hundred dollars each of annual revenue. Instead, Nimbit will target higher-end individual customers who will bring in $3,500 a year each in revenue. "We've got a better story to tell," he says. But he's quick to add that the changes don't represent a major strategic shift. "Those kill companies," he says. "A company has to stick to its original vision until that vision proves fundamentally flawed. And at that point, the company has a very big problem."

May 22, 2007
Charles River Ventures, Waltham, Mass.

Another day, another pitch to VCs. Today, Cramer is telling Nimbit's story to partners at Charles River Ventures. He runs the new VC pitch from start to finish, presenting Nimbit as "a next-generation business platform for the music industry employing a software-as-service model, and an SMB play representing an opportunity in excess of $1 billion through the network effect of leveraging captured data." So much for poetry.

At the end, a CRV partner compliments Cramer on having presented "a solid investment case." But the partner will quickly drop Cramer a note saying CRV is passing.

May 23, 2007
Commonwealth Capital Ventures, Waltham, Mass.

It's 7 p.m., and the large conference room is packed, especially at the end offering an expansive sushi and Chinese-food buffet. Several partners from North Bridge and Commonwealth are here, as are a handful of music industry insiders to offer their feedback. These include Ron Nordin, a former venture capitalist and software executive who has been financially backing some prominent Boston bands, and Nimbit adviser Don Rose, both of whom have the groomed, slick look of aging rock stars. Also brought in by the VCs is Jon Erik Borgen, a 30-year-old singer-songwriter who manages himself and earns $22,000 a year--the sort of customer Nimbit hopes to capture, if at the lower end of the range.

The deal, and very possibly Nimbit along with it, will be made or broken in the next few hours. There are no real backup funding plans, and Nimbit has a month's worth of funds to draw on.

The crowd is fairly gregarious, and moods soar even higher when, just after they all settle down to seats and put down their chopsticks, one of the partners reads his fortune-cookie message aloud: "The universe without music would be madness."

Cramer takes immediate control by giving himself a power introduction: Nimbit CEO and a 26-year veteran of software start-ups who has guided eight companies to six successful exits. (He twice left companies for other opportunities.) The intros run around the table, bringing things back to Cramer, who signals Faucher to begin the presentation.

This turns out to be a calculated move. The partners by now all know Cramer and the business case. The trick tonight will be to win rave reviews from the music insiders. And that calls not for Cramer's hard-edged business gab but for ex-rocker Faucher's passionate view of Nimbit's mission to empower independent musicians.

As Faucher describes how Nimbit will rescue the beleaguered artist from the claws of iTunes and the drudgery of staying on top of 20 different websites, Borgen, whose looks are a rugged riff on the haunted-artist motif, can't keep from loosing an enthusiastic "Wow." All eyes turn to him. "If someone offered me a way to keep everything up to date, it would be huge," he says.

Borgen's enthusiasm proves contagious, and the partners and insiders suddenly can't seem to find enough things to love about Nimbit. "Doesn't this have the potential to become a virtual label?" asks one partner. "The timing is perfect, because bands are shifting away from labels and trying to do more with their managers," says Nordin. "All the indie labels will support this," adds Rose. "Could Nimbit sponsor showcase events in different cities?" asks Borgen, whose opinions seem to carry great weight tonight.

The meeting starts to dissolve into bubbly side conversations, but Nordin signals for the group's attention. "I believe there's a huge market for Nimbit," he says. "But I have some anxieties. There already are ways to do all of this separately, and I'm not sure the message that you can do it all in one place is enough to pull people in. Nimbit is offering more efficiency, but it would be better if it could offer more functionality--if it let you do something you couldn't do anywhere else."

Cramer, who has been content to let everyone else do the blabbing as long as the talk is happy, immediately jumps in. It's true, he says, that websites have been springing up to address every niche that's out there for independent musicians. But that's left musicians facing a fractured industry that's just begging for centralization.

The crowd doesn't seem to buy it. "It's a lot to ask someone, to move everything they've been doing on these other sites to Nimbit," says a partner.

"If you don't figure out a way to move a large number of people to Nimbit as fast as possible, you won't be nearly as successful as you need to be," says another.

Cramer, Faucher, and Antoniades all start to reply at once, but Nordin cuts them off. "I had a couple of guys from some of the bands I work with go to your site," he says. "They saw things they liked, but not enough to jump."

This lands like a bomb and is followed by a moment of heavy silence. But Cramer quickly recovers. "The site today doesn't reflect the vision of the business," he says. "There are lots of things we can do to get people to the site. Not one big magic thing, but my experience in business is that it takes lots of effort and tuning and iteration to figure it out, and once you do that, you just turn the crank and scale it up."

This doesn't do the trick; the crowd seems to want the one big magic thing. A host of new objections now spring up faster than Cramer can respond. Wouldn't it be difficult to build software that can automatically dispense good advice to musicians in all situations? Aren't these market numbers suspect? Couldn't Nimbit be torpedoed by a competitor that simply took a smaller cut of the musician's revenue, or even no cut at all? Wouldn't it be better to take a small monthly fee?

Seizing on this last point, one of the partners asks Borgen if he'd be willing to pay $10 a month for what Nimbit is offering. The room falls silent. All eyes are riveted on this young artist as he thinks it over. "I'd need more proof," he says, finally.

"We give him all this sushi and a personal pitch, and he still isn't sure it's worth $10," says one of the investors, playing it up for the room as a joke. Everyone laughs politely--except for Cramer, Faucher, and Antoniades, who smile gamely but look stricken.

Cramer tries again. "That's exactly the right answer," he says. "And that's why we want to switch from fees to a revenue-sharing model with musicians."

The meeting winds down with Cramer getting halfheartedly grilled about projected operating expenses--$320,000 a month and a head count of 38 by the end of 2008--though no one seems particularly engrossed in the numbers.

One of the partners offers what is clearly intended as a wrap-up comment. "I'm still not sure I understand it all, but it's definitely an interesting idea," he says. From the looks on the faces of the Nimbit team, this wasn't what they wanted to hear. Cramer and Faucher jump up to do whatever schmoozing they can as people filter out.

On my way out, I overhear one of the more senior partners ask Rose if he would green-light the investment if it were his money. "They've nailed the market," Rose responds. "The question is whether they can build the sort of site it would take and whether they have the right people in the company. I don't know how to answer that." This, coming from an adviser to the company, is not the ideal last word on the matter.

Word would come in to Cramer within a week that North Bridge and Commonwealth were passing. Within the next two weeks every VC contacted by Cramer in a new round of pitches would follow suit.

Jun 22, 2007
Bruegger's Bagels, Weston, Mass.

It is hard to reconcile the tentative Bob Cramer sitting in front of me with the on-top-of-the-world fellow I met eight months ago. As he speaks, I think of one of those flickery, translucent Star Wars holographic projections sent from light-years away.

He seems to read me. "I was cocky back at the beginning, wasn't I?" he says. "I was telling people not to call me. I thought I could be picky about opportunities."

Not anymore. He tells me he's going to send out a barrage of e-mails to all his contacts. "I'm telling them that I'm ready and anxious to do something," he says. "I won't mention Nimbit. Or I'll say, 'I just finished a project.' I'll send it to executive recruiters, too. Even though I'm the one usually hiring them."

The sky has been darkening, and it starts to rain heavily. Cramer stares out meditatively at the downpour for a moment before suddenly remembering he has left the top down on his car. He bolts out the door. When he returns he's soaked.

Sitting down again, he reboots into what has become a sort of litany of second-guessing himself about Nimbit. "It would have really helped to take the reins earlier," he says. "We could have hit the proof points earlier. Maybe. Who knows?"

Nimbit, as it turns out, is not dead. Another $250,000 scraped together from the angels has left it on life support, its 20 employees cut down to 12. Cramer has tried to negotiate a partnership with a CD production company that would have brought in some money, but the deal is taking longer than expected. Antoniades is gigging again to make ends meet.

"I had envisioned Nimbit as great fun," Cramer says. "But the fun never materialized. One of the things that has come out of all this is that it's better to build a great company in an unexciting industry than to end up struggling in an interesting industry. You might think the data-storage market would be boring. But what's exciting isn't the type of market you're in; it's putting together a new strategy, a new business model."

Besides, he adds, it's not as if he's turning his back on his artistic side. "I still have my music studio in my home," he says.

August 16, 2007
Starbucks, Wayland, Mass.

Cramer is engrossed in Treo messages when I arrive. He seems relaxed and energized.

He recounts how he recently considered taking the CEO job at a database company with big potential. But the second round of interviews spilled into a scheduled family vacation, and he refused to change his plans. When he returned, he learned the company had gone with someone else. He was a little surprised and disappointed but felt he had made the right decision. After all, he was just following another of his rules: "Never regret doing a family thing over a business thing," he says.

Besides, he can afford to pass on that opportunity, given that so many others are coming his way. He ticks off a list of suitors: a computer security company, a data-storage company, and, particularly intriguing, a company building a cutting-edge data-messaging device. Meanwhile, he has been spending two days a week as temporary CEO of a disaster recovery company. "The VC begged me," he says. If it doesn't work out with any of these companies, he may have a different sort of position open in which to bide his time: A venture capital firm is talking about making him a partner in charge of nurturing some of its prospects.

Still, Cramer notes that he is not going to turn up his nose at any offers that look promising. "I didn't jump at anything last year, and if I don't jump this time, people might not listen to me the next time I tell them I'm looking," he says. He also has a less Cramer-centric view of the Nimbit adventure. "I was incorrect to feel that just because I was behind a project, it was going to get funded by top VCs," he says. "I still feel to some degree we would have had a better shot at it if it had been my show from the start, but it wouldn't have guaranteed we'd raise the money."

He talks for a minute about how Nimbit is making real progress in building audience and gaining partners and buzz, in spite of the tight budgets. "I fell in love with that company," he suddenly says, as if it is an explanation of everything that has happened to him over the past nine months, as well as a declaration that it is behind him now, a sort of passing madness. Then he adds, "If I was available, I wouldn't rule out my coming back as Nimbit CEO."

Postscript: In mid-October, Cramer took the CEO slot at Tervela, a data-messaging company based in New York. Cramer describes it as "a billion-dollar opportunity." He's still on the board of Nimbit, where angel investors have continued to chip in to keep the company afloat. Nimbit is steadily adding customers--about 3,000 artists now use the site. Faucher speaks highly of Cramer. "Bob was a fantastic mentor," he says. "There are lessons that I'm still trying to internalize."

David H. Freedman is an Inc. contributing editor.

IMAGE: Chris Buck
Last updated: Jan 1, 2008

DAVID H. FREEDMAN

A Boston-based contributing editor, Freedman is the co-author of A Perfect Mess, which examines the useful role of disorder in daily life, business, and science.




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