Business Wars

At the dawn of the dotcom era, a Silicon Valley tech geek on a personal vendetta rolls out the world’s first e-commerce site. Vintage lunchboxes? Second-hand guitars? B-list celebrity autographs? It all finds a home on AuctionWeb, and before long the site’s growth is skyrocketing. But founder Pierre Omidyar isn’t prepared for the infrastructure challenges that come with turning his pet project into a real company. Brownouts and site outages soon follow, raising the ire of customers. And without a way to close transactions online, AuctionWeb might be doomed before it takes off.

As eBay gathers steam, a libertarian chess champion and a programmer who fled Communist Ukraine team up to change the world with their encryption software. But when their plan to piggyback on the ubiquitous Palm Pilot hits a snag, they stumble upon a new idea. The concept is so revolutionary, it will change the landscape of e-commerce and turn the fledgling company into a viral phenomenon. There’s just one problem. PayPal is set on a collision course with the one company it needs to succeed: eBay.

In the midst of the dot-com boom, there's also a lot of dot-com bust. PayPal desperately needed to grow but they companies who'd raised millions more suddenly disintegrate. The solution was so simple it seemed almost illegal - let the converted proselytize. And they do to incredible results. It doesn't take long for eBay to notice but there's nothing they can do to stop PayPal's viral momentum.

Remember the summer of 2000? The Olympics were in full swing and PayPal was under attack. Not from eBay, but Russian hackers. In looking for soft targets in the early days of the untethered Internet, PayPal was the fattest cow. On top of that, there are competitors, and they’re catching on fast. Between the money stolen from hackers and competitors, PayPal has to figure out a way to survive, and fast.

By late 2000, PayPal and X.com are yoked together, with X.com CEO Elon Musk leading the newly combined company. But it’s a rocky marriage: PayPal’s founders clash with their new leader over everything from his imperious management style to his choice of server platforms. Finally the PayPal loyalists decide there’s only one option left: it’s time to engineer a coup.

PayPal is running out of time. The online payment service is hauling in new users, but its bottom line is bleeding red. Without a buyer to pump it full of cash soon, the company could go under. Should it take the safe route and sell out to its longtime nemesis eBay? Or should it risk the open market with an initial public offering? Why not both?

We hope you enjoyed our series on eBay vs PayPal. Here to discuss her thoughts on the PayPal mafia alums is Kara Swisher. Swisher is the self-described "grumpy lady of tech" and host of the podcast Recode Decode. She's known for her tough takes on Silicon Valley, is Silicon Valley royalty, and even had a cameo in Season 1 of HBO's Silicon Valley. Have we mentioned Silicon Valley enough? Here's our conversation with Kara.