There's a New Man in Town

E-Diaries

He's smart. He's experienced. He's Scottish. He's our new CEO

Being the CEO of an Internet start-up in San Francisco carries loads of cachet. My mom practically collapsed with joy when I informed her of my plan to start a company; after years of hearing about the successes of her friends' "little lawyers," she finally had a better response than "Andy's spending some time exploring." The title usually plays well on dates, too, although whenever my friend Ellen is asked out by a dot-com CEO, she rolls her eyes and moans, "Don't tell me -- advertising-revenue model?"

Yet despite the prestige, my application to the Young Presidents Organization lies incomplete on my dresser. That's because even before I founded Gazooba with my pals Zen and Shanti, our venture-capital backers told us they would eventually bring in some "gray hair" with the experience to get us "to the next level." I began losing hair after a few months of running the company, but apparently that didn't cut any mustard. "Look, you're doing a great job here, Andy," said one of the VCs at our third board meeting. "But let's face it: the company's going to get a better valuation with a big name at the helm."

Andy's brain: "But I'm the CEO! It says so on my business card! I've hired 20 people! I've made all the decisions! I have the corner office! OK, I have a desk in the corner of the office. But still! I'm the CEO!" Andy's mouth: "Well, I'd rather be rich than famous. Got anyone in mind?"

So, with my pride lodged firmly in my esophagus, I embarked last December on the search for our new Grand Gazooba. Actually, the first step was to search for a professional searcher. Our VCs rounded up contacts at the usual suspects: Spencer Stuart, Egon Zehnder, and Korn/Ferry. I met with all of them, but despite their promises I didn't believe they'd give us a lot of personal attention, considering all the work they do for bigger clients. I asked one of our investors to dig deeper into his Rolodex, and he pulled out the Scott Swimley card.

At the time, Scott was a partner at Lautz, Grotte, Engler & Swimley LLC, a boutique executive-search firm I prefer to call LGES, if only to save ink. (He has since moved to Oak Technology Partners, an executive-search and investment firm.) Scott's a fast-talking, good-looking guy whose year-round tan testifies to his practice of dropping the names of CEO-hungry start-ups between holes at expensive country clubs. He boils down Internet companies the way Hollywood producers boil down movie concepts: "You guys are basically Amazon meets Amway meets Inktomi. I love it!"

But Scott's breathless enthusiasm morphed rapidly into a sober reality check. Sitting with us on our secondhand sofas, he delivered the start-up's version of Scared Straight. "You've got to be prepared for what happens when the new guy comes in," Scott said. "I've seen it a thousand times. First, you can all expect to be layered." My hand flew to my hair as I pictured myself wearing a Farrah Fawcett do. But Scott explained that layered meant we'd report to the new top dog's right-paw folks, if we were permitted to report to work at all.

"Second," said Scott, "this guy will get a huge piece of the company, as much as or more than the founders. Yet you will have to kiss up to him in every conceivable way, including showing up at 7 a.m. at San Francisco Airport with knee pads on if that's what he asks for. And third, this guy will probably be a guy, given the pool of experience out there." Jennifer Kaplan, our vice-president of business development, stared wide-eyed at that flagrant breach of political correctness, but even she seemed to appreciate the straight talk. I retained Scott with the customary gobs of cash and stock.

Despite Scott's prediction, the first serious candidate he sent us was, in fact, a woman. The CEO of a well-known private Internet company, she was leaving to make room for a replacement who would take the business public. The candidate had built that company from practically nothing to a millions-of-dollars something, and I thought she could do the same for Gazooba. She invited Zen and me out to lunch to discuss our vision for the company.

Over sushi and beer, we explained our idea to use the power of personal recommendation as a vehicle to market products and content online. Our candidate threw out all kinds of CEO-like proposals, including migrating the service to wireless platforms and using the data we'd gather to build recommendation profiles for customers. "This talk is really getting me hard-on," cried Zen, using a phrase he picked up from the movie Top Gun, in which a character uses it to signal enthusiasm. Only her long training in the graces of CEO-dom prevented our candidate from spitting beer all over the maguro.

I don't know whether my chief technology officer's inadvertent sexual harassment influenced our candidate's decision, but in the end she said thanks but no thanks. She did agree to join our board, however. And I made a mental note to go over English slang with Zen.

In the months that followed, Scott sent over a candidate here, a candidate there. The drill consisted of an in-depth interview with me at our offices, followed by a visit to our lead VC. Sushi lunches were reserved for second dates.

One of our top contenders was a former military guy who vowed to get us in shipshape. But ultimately, his promise to "blow out the business" raised doubts that he could delicately steer us through the rough waters ahead. Besides, his crew cut was very un-Gazooba. A veteran of the high-tech-conference industry had potential, but our VCs ruled him out because he lacked Internet experience. Most of the others just weren't sufficiently CEO-ish; that is, when I imagined myself as an investor, I wasn't overcome by the desire to throw all my money at them. Scott told me there are more than 100 Silicon Valley CEO searches under way on any given day, so I'd need to be patient.