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Author Topic: The 20 Worst Venture Capital Investments of All Time  (Read 1817 times)

app103

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The 20 Worst Venture Capital Investments of All Time
« on: November 22, 2007, 01:20:01 AM »
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Some things were just never meant to be, but that doesn't mean that investors won't pile millions of dollars upon a bad idea — or even a good idea gone bad. Whether they crashed and burned or sucked investors dry, these ventures just didn't work out. Check out our graveyard of dreams and money to get a look at VC (venture-capital) investments that just weren't wise.


Ralf Maximus

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Re: The 20 Worst Venture Capital Investments of All Time
« Reply #1 on: November 22, 2007, 01:52:23 PM »
Ah, the scent of somebody's brilliant business plan making contact with the real world and imploding.  It smells like... stupidity.

I remember seeing the ads on TV for WebVan (#3 on the list) and thinking they were a joke.  Some kind of parody commercial, where the real sponsor's name would appear at the very end.  Order groceries on line?  Milk and eggs?  Really?  No!  Really?

WebVan *might* have succeeded if they'd made some different decisions. Others, like Boo.com, seem to have viewed their venture capital as Woo Hoo Free Money Everybody Gets A Porsche and seemed shocked, absolutely shocked when the end came and they weren't successful.  Wasn't sticking .com on the end of your name supposed to guarantee success?

In the summer of 1999 my business partner and I tried to get a small business loan to start our own dewey-eyed vision of the future.  Unfortunately, our company had nothing to do with the internet aside from a coporate web site.  The meeting with the bank loan officers were surreal.

"So, tell me what your internet company does."

"Ah... well, it doesn't have much to do with the internet.  What we do is--"

You could then see the interest draining from them, their eyes darting towards the nearest exit, their formerly firm grip on the check-signing pen now lax, the briefcase mysteriously shut when a moment ago it'd been invitingly full of applications and "Let Us Help You Start Your INTERNET Company!" glossies.

The one and only time I contacted an ex-boss to see if he was interested in a buy-in resulted in this keen observation: "Ralf my boy, why should I give you any money?  Your plan says you can give me a return on my investment of $3 for every $1 pumped in.  I've got some money in a dot-com that'll return 10 million dollars for every buck I put in."

He got me there.  I thanked him and left, never realizing how catastrophically wrong his reasoning was until the market exploderized at the turn of the century.  I wonder how many 10-million dollar bills he ever got to cash?  *chuckle*

Another story: I kept in contact with an ex-coworker, the CTO of a medium sized company.  He went on to do mysterious things in New England, the kind of things that, while clearly legal, he was never able to describe adequately to the likes of me.  Complicated big business things.

Anyway, we're chatting on the phone (circa 1999) about how crazy the .com investment thing is, and he tells me about this recent episode in his life.  He goes to lunch with a venture capitalist pal of his, and idly mentions this idea he had for a web site and how it might make some money.  The way he relates it, the whole thing was a "wouldn't it be super keen if you could buy pre-shaved monkeys on the internet" kind of hare-brained idea.  He threw it out there as a joke, knowing the guy processed dozens of stupid ideas a week.

Lunch over, he drives home -- maybe 30 minutes.  By the time he unlocks his apartment door, the fax machine is already chewing through a ream of paper.  He's got incoming resumes from coworkers, friends, acquaintences all wanting to work on his fabulous new project!

Thank god it was meant as a joke, otherwise www.PreshavedMonkeys.com might be on that list. 

app103

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Re: The 20 Worst Venture Capital Investments of All Time
« Reply #2 on: November 22, 2007, 11:35:45 PM »
Thank god it was meant as a joke, otherwise www.PreshavedMonkeys.com might be on that list.