(This is chapter 26 of my ongoing memoir of the Internet industry.)

The day I began working at iVillage was the first day I ever found myself truly excited to meet the president of a company I worked for. But there has never been, and probably never will be again, a CEO like Candice Carpenter.

This wiry and fierce woman was one of the most controversial figures in the Internet industry in the early months of 1999. Her company’s IPO was widely expected to succeed, despite the fact that many industry commentators considered her a bewitching fake. It was true that she could thrill a crowd (I had become inspired to join iVillage myself after hearing her speak), and she was obviously thrilling Wall Street as well, even though iVillage was the epitome of a money-losing, big-spending dot-com, with a highly uncertain financial future.

To those who wanted more substance in their dot-coms — more e-commerce revenue, more advertising dollars, fewer press releases, fewer TV commercials — iVillage represented the worst of hype-crazed Silicon Alley. I guess that’s why I thought Candice Carpenter was so cool.

She would take the criticism and spit it back in their faces. On talk shows and newspaper or magazine interviews, Candice Carpenter would insist that iVillage had a great business model and true staying power (despite the current lack of revenue), and I never heard her back down or hedge this bet. She always spoke with style and verve, often while wearing skin-tight leather dresses, pink jungle-print mini-skirts or other truly strange outfits, and was known to say outrageously philosophical things about the true meaning of work, about why people are afraid to compete, about the business world as a character-building exercise. Most of the things she said made sense to me.

Candice Carpenter hated conformity, and she hated “business as usual”. Work was a moral challenge, a pursuit of inner greatness. If you worked for her, you should show up each day expecting to be pushed to the limit. Your territory was never safe — you must be willing to defend your ground at any point, because if somebody didn’t like the way you were doing your job, they had the right to move in and shove you aside, replace you, ignore you. You, meanwhile, had the right to fight back.

Darwinian anarchy reigned; this aggressive corporate culture began at the top and truly filtered down to every level of the company. It was because of these implicit rules of play that the system administrators in the technology department had been allowed to depose their former boss simply because they didn’t like the way he tried to manage them (and this was why I was slightly nervous moving into the role of this team’s new boss on the day I joined the firm).

IVillage was a modern media company structured according to the law of the jungle. But new social rules emerged to make this system work (and, indeed, it did work). For instance, in Candice Carpenter’s world, there was no shame in failure. The former technology manager who I was replacing had not been fired after his team mutinied against him. Work was a character-building exercise, so he was given time to lick his wounds and get back in the game, if he could find a new way to make himself useful (and, to this manager’s credit, he eventually did).

IVillage had a famously high employee turnover during these years, but this wasn’t because a lot of people were fired. People were often mistreated, humiliated, worked to near-insanity, ignored and left for dead — but not fired. IVillage would wait for them to quit, and most often they did.

It’s a funny thing that this Darwinian work environment powered a company with a highly feminine public image. To the outside world, iVillage was where women chatted about parenting and sex and favorite TV shows. Indeed, Candice and her partner Nancy Evans (a well-connected former book editor who lacked Candice’s charismatic public flair but was every bit as tough) had put together a powerful package that played like a dream on Wall Street. Advertisers would always want to reach women, and iVillage had thousands of popular message boards that engaged women in deeply personal and emotional ways.

But an online community company had to excel in both advertising and e-commerce to pull off a great IPO in the 1999 Internet stock market, and iVillage had recently made a very smart move by acquiring a start-up called iBaby.com that promised to be the Amazon.com of the baby-products business. Since consumers spent more money each year on baby products than books, this seemed to promise that iVillage would eventually become bigger than Amazon. (In fact, there were several things wrong with this formula, yet it was the acquisition of iBaby.com that completed the picture Wall Street needed to see before iVillage could launch its initial public stock offering).

As the company neared its big IPO day, Candice and Nancy Evans were spending much of their time traveling around the country explaining iVillage’s value proposition to potential investors while Chief Financial Officer Criag Monaghan and Chief Operating Officer Allison Abrahams stayed in New York City to run the day-to-day operations. Both Craig and Allison had clearly laid out my first day’s responsibilities: I needed to solve the crisis among the systems administrators who kept the web servers alive. I had heard fearful things from Craig and Allison about Camille Currim, the rebellious and completely unreasonable top sys-admin who refused to take direction from anybody at all. Expecting an ogre, I was surprised to meet a charming woman with a soft voice and a friendly smile.

Camille knew why I was there and conceded that she had allowed communication to completely break down. But she insisted to me — contradicting everything I’d previously heard — that she had never refused to talk to anybody, nor ever refused to compromise. She was not concerned about herself, she told me, but about the overworked techies on her team, Ted and Mikey and Mozam. She described their salaries and their typical working hours, and I had to agree that they were underpaid and overworked. She explained that it was very difficult for them to keep up their spirits in these hyperactive pre-IPO days when they had never been given significant stock options of their own. She did not want to harm iVillage’s stock market debut, she told me; she cared deeply about the company and was very hurt that some of the executives had come to hate her simply because she stood up for her staff. She was willing to agree to any reasonable terms to allow the crisis to end, and she seemed happy enough to accept me as her new manager.

Our first meeting went surprisingly well. I spent the rest of my first day at iVillage talking to the rest of the tech staff, which included Ted and Mikey and Mozam on the sys-admin side, Jim Berrettini, Evan Sable and Scott McKenzie on the application development (C++, Perl, TCL, Java) side, and an effusive Lebanese project manager named Fadi Farhat who was responsible for making sure the company’s software code base would be “Y2K-compliant” for the new millennium heading our way.

I liked the tech team a lot, and was able to give a happy report to Craig Monaghan at the end of my first day. He then told me some news that presented an unexpected curve: he had finally hired his new Chief Technology Officer, a guy named Rich Caccapollo, who would be arriving in two weeks.

I’d known that Craig and Allison were looking for a top tech guy (and I was totally at peace with the fact that the CTO wouldn’t be me, since I knew I was a hands-on techie/manager who lacked the business education and smooth managerial skills of a professional executive). But I didn’t expect that they’d make the hire so quickly, and this put me in an awkward position with regard to all the team members I’d just met.

I would be working for this new person, and his responsibilities would overlap directly with mine. Everybody who worked for me would also work for him. I’d just spent my first day putting together my own ideas about how this tech department could best move forward towards the company’s IPO, but this new person — whoever he turned out to be — might have completely different ideas.

It was only my first day at iVillage, and the jungle had just gotten a little more crowded.