My favorite part (with reference to eToys):<p>"They ditched a perfectly working MySQL application and migrated to Oracle which caused them to hire Oracle consultants $2000 per day and spend millions on Oracle big-iron."<p>Reminds me of when the ads manager at Google decided we needed to ditch MySQL and get a "real database" for the ads system. "Real database" in that case meant Sybase, but it was still a barely mitigated disaster. Sometimes it seems as if the "real" databases are just a colossal scam.
How about Iridium? Over $5 billion invested, sold for $25 million.<p><a href="http://www.wired.com/techbiz/media/news/2000/03/35043" rel="nofollow">http://www.wired.com/techbiz/media/news/2000/03/35043</a><p>Right now it is hard to compete with bing.com, losing 2.5 billion per year.
Oh ye of little history. Do none remember Xanadu still? Inspired by Eric Drexler's call for hypertext as a way of making society more intelligent, they tried to invent the Web, a decade too early and with standards much too high (cached local copies which would still receive micropayments, two-way backlinks), and never solved the incredibly difficult programming problems they were tackling before Mosaic and HTML came along.
Ah, how do I miss f'dcompany.com. :)<p>I'm still impressed by the VA Linux IPO:<p><a href="http://en.wikipedia.org/wiki/Geeknet" rel="nofollow">http://en.wikipedia.org/wiki/Geeknet</a>
Anyone remember BroadVision? (shudder!)<p>For a time there, I worked for UNext, an online University who decided that it was not enough that their site was powered by Broadvision (using highpriced broadvision consultants), but that their Intranet needed to run on broadvision as well. Oh swell!!<p>On top of that, they decided to contract those consultants straight out of Broadvision Inc itself, at over $300 an hour.<p>The CEO drove one of the $100k Mercedes Jeep type SUVs, imported ofcourse.<p>Not soon after, I left Chicago to go back to the Valley. And they ran out of money soon after.
Great to see Kozmo mentioned a few times, I still to this day have quite a few Kozmo shirts they used to send out for free.<p>I'd like to add WinStar, they had people going pretty much door to door in Manhattan selling services, I got a pretty decent free lunch off them.<p>I'd also nominate GovWorks, not huge in terms of money burned or technical blunders, but I credit the movie startup.com for really exposing some sheer ineptitude.<p>Edit: How could I forget Globix, the colo that had a coffee shop and a gym.
Metricom burned through $600M of Paul Allen's money building out an early wireless network that hardly anyone used, then folded. I don't know if this is quite in the "Internet startup" category since it wasn't a Web site, but it certainly was Internet infrastructure.
I guess technically they don't qualify, but surely Microsoft's web properties have to be right up there. Billions later, they have yet to turn a profit.
boo.com was pretty impressive - $188 million in <i>six</i> months and all lovingly documented by their co-founder in CEO in a fairly unapologetic book:<p><a href="http://www.amazon.com/Boo-Hoo-Dot-com-Concept-Catastrophe/dp/0099418371" rel="nofollow">http://www.amazon.com/Boo-Hoo-Dot-com-Concept-Catastrophe/dp...</a>
Definitely drkoop.com. Its market cap at one point was around 1.3 billion.<p><a href="http://www.nytimes.com/2002/07/16/business/technology-briefing-e-commerce-drkoopcom-is-sold-for-186000.html" rel="nofollow">http://www.nytimes.com/2002/07/16/business/technology-briefi...</a>
They ditched a perfectly working MySQL application and migrated to Oracle which caused them to hire Oracle consultants $2000 per day and spend millions on Oracle big-iron.
They were hiring out of control.
They decided to build a new building to house their new offices because the Ocean Park Blvd offices in Santa Monica weren't pretty enough.
They opened up a London office in Piccadilly Circus, the most expensive rental area in London.
They replicated their entire USA dev team in the UK for no apparent reason.
They started work on a German operation.
They launched a warehouse in Belgium (my baby) to service Europe.
All execs flew first class between Europe and USA.
Engineers were flown around the world as needed.
I was even told to expense my groceries while in Santa Monica for 3 months. Trivial, but the little things add up.<p>--- none of above would have happened, had they hired professional managers, not a bunch of children willing to spend every single dime on anything other than business itself.<p>apply that list to any business, including apple, google, microsoft, oracle, groupon, you name it, the result would be the same disaster as with etoys.