From beginning to end, the story of a failed parking startup

I heard a rumor once, and I have no idea how true it may be. But the rumor goes something like this: parking lots, beyond being ridiculously lucrative and turn-key businesses, are also fantastic money-laundering or tax-dodging opportunities. And so many of them are owned by shady characters, or shady companies. These types don't necessarily want to deal with things like processing credit cards, or getting into paper trails (although some modern parking lots are using credit card readers, for convenience's sake).

This sounds pretty fanciful, but it doesn't seem entirely implausible.

Occam's Razor says that the garage managers weren't interested because they're doing just fine, and your service wasn't solving a greater problem than the inconvenience of manually dealing with bids would cause. But I wonder if there's another factor at play here. :)

Anyhow, this is a great recap of your approach, and I'm sure it's been a fantastic learning experience for you both. Thanks for writing this, and for sharing it! On another level, it frustrates me to read your story: it seems like you guys had identified a real problem with users ready to try it out, and the other side of the market just didn't have the same degree of need. That sucks.

This is 2 years old. Here's a better version: http://chrishoog.com/the-helloparking-postmortem-a-look-back...

The last part is spot on, and says what you were probably just about to try to tell him (self-righteously I'd bet!).

The AirBnB of Parking. The ZipCar of Parking. The Priceline.com of Parking. The Groupon of Parking.

There's your problem. You kept imitating other businesses instead of doing what makes sense for your customers.

I think that is the hard part in a startup "doing what makes sense for your customers". Many times, its difficult to find what customers want. Some times, even customers might not know they would need it until you actually have the product ready to use.

I know it would probably not be easy[1], but it seems like someone who bought a parking lot then started building the app might get pretty good result.

1) buying costs $ and running is a pain