Jeff Bezos, Jack Ma, and the Quest to Kill eBay

The right — and wrong — way to compete with a locked market

Steve Yegge

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Illustration: erhui1979/Getty Images

This is the story of the first time Jeff Bezos got something spectacularly wrong. It’s the story of why he was wrong, what happened afterward, and what we can learn from it. It’s also the story of how Jack Ma tackled exactly the same problem a few years later, and got it right.

For this particular story, I don’t have all the details. I may get a few things slightly wrong. I wouldn’t treat this post as a historical record so much as a way to get some life lessons from guys like Jack and Jeff—without spending as much tuition money as they did.

The Birth of Mr. Tooth

I’m going to venture a guess that you’ve never heard of Mr. Tooth. He looks like this:

It’s pretty goddamn hard to find a picture of Mr. Tooth these days. A Google search for “amazon auctions mr tooth” will produce nothing. I had to use the Wayback Machine, and even that took quite some time because his life was so short.

Mr. Tooth wasn’t purged from the internet through some vengeful move by Amazon to hide all traces of their embarrassment. No, the simple truth is that Mr. Tooth was so ineffectual that nobody ever bothered to remember him.

When I started at Amazon back in December 1998, it was a crazy time. A historic time. There was an electricity in the air, and it wasn’t just the smoke from the bar below us, there in the old Columbia building on 3rd Avenue. Everyone could feel history being made, and at the center of the fire was Jeff himself. Even back then, in a company of maybe 100 people (sans ops), he was already a cult figure with protected access.

Start looking for another related market to enter, and you can then sneak up on the original market from the side.

At the time, Jeff had never been wrong about anything. Certainly not in any big, meaningful way. Everything he launched was pure gold. First he launched Books, and who the hell would have ever guessed that an internet bookstore would catch fire like that? Then, he successfully launched Music, taking aim at record stores, and…

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Steve Yegge

Steve Yegge is ex-Geoworks, ex-Amazon, ex-Google, and ex-Grab, with nearly 30 years of tech industry experience. Nowadays he’s pretty much retired.