Cool rules

Why are some of the best minds of our generation working on a better way to send out party invitations?

Published September 22, 1999 4:00PM (EDT)

We are sitting in a trendy San Francisco restaurant, finishing our coffees, when Josh Silverman springs the question on the couple sitting at the neighboring table.

"Have you ever gotten an Evite?"

Our neighbors stare blankly at Silverman, who has already exchanged some small talk with them earlier in the evening. The man gracefully retreats to the relative safety of the appetizer chatter: "What did you say your company was called again?"

"Evite," says Silverman. I cringe a little, but he is completely unfazed. You see, Silverman and I have a little dispute going. He thinks it's more likely than not that somebody in this restaurant has used his company's Web site. I think this is improbable, and I have threatened to put it to the test by going around the room and asking.

Of course, I was not going to make good on this threat, because in the conventional scheme of things there are few things as inherently uncool as walking through a roomful of strangers and asking them if they have used a new Web-based application. But there, in a nutshell, is the difference between Silverman's world -- the world of Silicon Valley start-up life -- and everyplace else's: In Silverman's world, there is nothing as cool as telling a bunch of strangers about your new company.

In the hierarchy of contemporary business cool, there are big companies (uncool), little companies on the bleeding edge of technology (cool), successful companies (cool), companies whose stock has taken a nosedive (uncool), start-ups on the verge of going public (very cool) and finally, at the pinnacle, the sine qua non of Silicon Valley cool, the "raw start-up" -- the start-up that's still working on its final business plan, the start-up that is just about to get its first millions from professional investors, the start-up that has a three-room office with four desks in each room.

Silverman has been CEO of Evite since it was a raw start-up. In his world -- the world of programmers, suits, salespeople, visionaries, strivers, geeks and assorted foot soldiers in the Net gold rush -- that makes him the bomb.

According to its promotional literature, Silverman's company is "a Web-based Group Activity Organizer." Put more simply, that means that Evite is a tool for creating invitations. The idea is that a user goes to Evite, puts in the type of event and the guests' e-mail addresses. Evite sends out an invitation, and everybody involved uses the Web site to post their thoughts about the event. For a dinner, that can mean planning the menu; for a conference, it can mean deciding the agenda.

When I first set out to write about Evite, I believed that Evite exemplified a new breed of instant companies trying to capitalize on the mania for anything with a ".com" in it. Evite does provide a useful service, but I didn't see it as a company that could remain independent indefinitely.

Over the last three years, a few big Net players -- America Online, Yahoo, Lycos, Microsoft, Excite@Home -- have bought company after company to build out their portal sites. They have bought Internet chat companies, online white pages, Web-based e-mail and calendars -- everything they can get their hands on to make their sites "sticky" or to keep up with the rest of the bunch. The best-known of these acquisitions was Hotmail, the free e-mail company bought by Microsoft for $400 million. Even some of the less-publicized acquisitions have been tremendously lucrative for their founders. For instance,, a company that developed a Web-based calendar, was bought by America Online only one year after launch for a rumored $225 million.

In this market, it's easy to see why one might want to build "an acquisition play," and I had Evite pegged as a company whose main reason for existence was the prospect of a quick sellout to someone bigger. However, in talking to the people behind Evite, the company's prospects (and, consequently, the financial motivations of its founders) seemed less and less important. What did become important was understanding what it was about a company like Evite that would engender the kind of devotion that would make an otherwise normal person perfectly happy to walk around a restaurant asking weird questions of total strangers.

In San Mateo, the San Francisco suburb where Evite has its offices, it seems that everybody is starting a company or hoping to start one. In Northern California in 1999, starting a company is seen as just about the coolest thing you can do, but simply describing what Evite does fails to capture that sense of cool -- the aspiration that goes into the start-up life. It was that aspiration that I went down to San Mateo to understand.

Evite has its origins in a company called Ootleworks, an ambitious venture started by two Stanford engineering students, Al Lieb and Selina Tobaccowala. At age 24, Lieb is chief technical officer of Evite; Tobaccowala holds claim, at the age of 22, to the title of vice president of engineering.

As computer science students go, Lieb and Tobaccowala were really good. Lieb graduated from Stanford with a 4.2 average, and while I am not generally impressed by degrees from expensive colleges, I am impressed by this one, simply because I had not previously considered that a grade-point average could go above 4.0. Tobaccowala, meanwhile, was one of only 18 women to graduate with computer science degrees from Stanford in 1998.

Both of them had sterling and well-compensated careers ahead of them. Lieb in particular was a star: During a short stint at Microsoft, he had developed a Java applet -- a small program -- for the Expedia travel site that was demonstrated on a huge screen at a key Microsoft product conference (this is a little like a congressional intern writing a piece of legislation) and was later licensed to companies like American Express. This means that as an intern, Lieb was generating a measurable revenue stream for Bill Gates.

The problem with having a talent for a very marketable skill like computer programming, however, is that it prepares one for a very lucrative job with a very circumscribed horizon. Lieb and Tobaccowala were sorely underwhelmed by their experiences in corporate America. "At Warburg Pincus," says Tobaccowala about her summer job at an investment bank, "people would see what I did and say, 'This is cool, but I don't use a computer.'" At a technology company, the prospects were a little more attractive.

That left Lieb and Tobaccowala searching for an alternative, and the result was something extraordinarily ambitious. In 1997, Lieb's last year at Stanford and Tobaccowala's junior year, they developed the rudiments of a programming language and development system that would take information from the Web and stream it into a database. The application was called Ootleworks (which later became the name of the company), and it used a programming language called Ootle.

If one is not extraordinarily familiar with the details of programming, then the value of this will probably be less than clear. But most programmers will recognize the challenge of quickly moving information between different kinds of databases as both technically interesting and commercially important. It is the same kind of programming challenge that lies, for instance, at the core of shopping bots that compare prices across the Web. The value of Ootleworks was in the possibility of customizing it to solve any number of problems. In that sense, asking, "What does it do?" is like asking, "What does a computer do?"; the answer is "What you program it to do."

The problem is that creating a big, ambitious, free-form application meant Lieb and Tobaccowala had to sell to the same big companies they had tried to stay away from in the first place. It wasn't a happy marriage. Lieb says he spent one meeting with a corporate MIS manager thinking that in the time the executive took to explain the features he thought Ootleworks lacked, Lieb could have written the code that would add them.

That's when it became clear to everyone that something had to change. MIS managers didn't understand what Ootleworks would let them do. The small amount of money that Lieb and Tobaccowala had raised from parents and friends was running out. Meanwhile, Junglee, a company that had solved a very similar programming challenge to develop a shopping comparison service, was bought by Amazon, the giant Web retailer, for an astounding $173 million in Amazon shares.

Wait a second  if you can't sell a powerful database application with a myriad of uses, and you know that a comparatively simple product built from very similar code can bring you tens or hundreds of millions of dollars, what do you do?

You pare down your huge mass of code to come up with something simpler. And that's exactly what Lieb and Tobaccowala set about doing.

This is the point at which Silverman comes in. Silverman had gone from business school at Stanford to a senior job at ADAC laboratories, a maker of medical equipment. If that sounds like it could have been dull, it was. "I just didn't care about gamma cameras," Silverman says bluntly.

Silverman had been spending his Saturday mornings brainstorming with a friend, trying to come up with an idea for a Web start-up. He approached the problem with a sensibility very different from the programmer sensibility that Lieb and Tobaccowala had brought to their venture. He didn't start with the code; he started thinking of an application that millions of people might want to use.

The result of Silverman's brainstorming was ToGather, a Web-based event planning application. Silverman quit his job and got to work launching the company. Then a friend sent him an e-mail, telling him that Tobaccowala and Lieb were way ahead of him on a similar project, Evite. He sent back an e-mail filled with expletives. Then he met with Lieb and Tobaccowala, and promptly signed on to serve as CEO -- the guy charged with turning the idea into a business.

With Silverman's entrance, things went into overdrive. Through his Stanford connections, he arranged a $700,000 loan to keep the company going. Then Silverman, Lieb and Tobaccowala went on a search for venture capital, the big money that would let them advertise a Web site to millions of Web surfers, scoring $7 million in funding. Finally, Evite -- the tiny company that had its origins in a Stanford dorm, a complex masterpiece of code and the urge of both its founders and its new CEO to stay away from the corporate rat race -- was off and running.

Every high-tech entrepreneur I have ever talked to, without exception,
has told me that his or her aim is to build a great company with a great
product that will transform (fill in the blank). So let it be stipulated
here that Lieb, Tobaccowala and Silverman all hope to build a great company
with a great product that will transform event planning.

However, the striking thing about the reality of a start-up company is how
little it is "about the product." The story of Evite, in fact, illustrates
exactly how little of the excitement of the start-up depends on the
product. The coolness of the start-up is in its aspirations, not in its
reality. It is to be found in the big ideas and the tough code-wrestling of Ootleworks' early days. To a lesser extent, perhaps, it might lie in
Silverman's Saturday-morning brainstorming sessions, in the frantic scrambling
for a new idea that would get Silverman out of the business of selling gamma
cameras. A part of the coolness certainly lies in the ground zero of the
experience -- the simple realization that life in a big corporation sucks.

The Silicon Valley idea that doing a start-up is the height of cool is
actually closely tied to the triumph of process over product. It's not what
you're making, but how you go about making it -- a kind of notion of
craftsmanship superimposed on the mores of the business world. (In fact, Tobaccowala has already consulted with an expert on corporate culture -- before the company is big enough for it to have any culture to speak of.)

The irony here is that the further along a start-up is in its life, the more
the aspirations that went into its founding get narrowed down to a single idea,
the product, and the more it becomes just like every other corporation.
On the surface one sees a niche idea -- a Web site for what is essentially a niche application, one of scores of new companies trying to create just one more little use for the World Wide Web. And yet that one niche idea is the result of two years of work by extremely talented people, the final outcome of a lot of big ideas.

I have no way of knowing whether Evite will grow, or sell out for millions of dollars, or eventually disappear. My bet is that it will be the second. The business of the big portal sites is in aggregating niche applications like Evite, and Evite has already gotten offers of a buyout.

Then again, other outcomes are also possible. Says Steve Jurvetson, a venture capitalist with the firm Draper Fisher Jurvetson, "Look at eBay. Before it went public, nobody would have said this is an obvious stand-alone company. Everybody thought, 'Of course it's an acquisition play that will be bought by one of the portals.'"

Either way, however, Evite has already embarked on the trajectory that is moving it from the realm of cool to that of uncool -- the big companies with narrow aspirations and big-company ways of doing things. Already, there are hints of that, and Evite's founders are aware of it.

"When we did our last round of hiring," says Silverman, "we took only people who had already worked in exactly the same position at another Net company. If I applied to work here now, I wouldn't even get an interview."

By Mark Gimein

Mark Gimein is a staff writer for Salon Technology.

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