You’ve heard of Moby Dick and the one that got away? How about 20 really bad investments? This list, posted today on and compiled by its editors, is a reminder of what burn rate really means, with a hint of what valuation once meant (traffic, not sales; notoriety, not fundamentals). It’s also a an excellent illustration of why venture capital firms aim for deals that look like they can deliver 100X returns–because there are a lot of losers along the way.

My personal favorite, Webvan, ends up as number three on this list. I was hoping for Webvan to succeed, because I hate shopping for groceries, and some of my family members were customers. Then they bought thousands of white vans and warehouse facilities, and crashed.

This company that once had about $800 million in venture capital ended up with $830 million in losses, with about $40 million on hand.

Number one, Amp’d Mobile, apparently decided to focus on people who didn’t pay bills, or so it seems from the description. I thought it had died because of the apostrophe in the name, always a bad sign.

While other mobile providers check for an ability to pay bills within 30 days, Amp’d let it go to 90 days and marketed to these risky customers. It has been reported that 80,000 of the company’s 175,000 customers were unable to pay their bills.

I won’t spoil the suspense, though, go read the list. And remember it the next time you want to complain that VCs are too focused on fundamentals.

Tim BerryTim Berry

Tim Berry is the founder and chairman of Palo Alto Software and Follow him on Twitter @Timberry.