One of the interesting things I've noticed due to the discussion about Yahoo!'s purchase of del.icio.us is how differently success is judged in the post-dotbomb technology startup scene. Specifically, I'll focus on two posts that gave me cause to pause this afternoon.

In his post Learning from mistakes Anil Dash writes

Best post I've seen today: Ari Paparo talks about the differences between del.icio.us and Blink. Blink was Ari's startup during the bubble, which raised $13 million (!) to build an online bookmarking service, but didn't take off with users.

The only way any of us gets to be a successful entrepreneur is by learning from others' mistakes, yet a lot of business culture focuses around never admitting that errors are ever made. So kudos to Ari, not just for being brave enough to be self-critical, but for helping a lot of new aspiring entrepreneurs to succeed

The only quibble I'd have is that Ari presents del.icio.us as having succeeded already. Josh and his team at del.icio.us have built a great app, but for as popular as they are with geeks, the hard work is to bring the concept of social bookmarking (or, if you prefer, a shared recollection tool) to a larger audience.

In his post Getting it right Ari Paporo writes

Congratulations to Josh on the del.ico.us acquisition. Yahoo will make a great partner for the bookmarking service.

Now a little part of me is cringing as I write this. Having founded a bookmarking company in 1999 with pretty much the exact same vision as the new crop of services, I’ve got to feel, well, a little stupid. (or angry, or depressed, or whatever). Maybe writing about it will make me feel better and maybe even help me make a point or two about product development.

When we founded Blink.com (no link love, it’s a crappy search site now) the founders and I imagined a self-reinforcing product cycle:

1. Consumers needed portable bookmarks so they wouldn’t lose them, would be able to access them from any computer, and could share them with friends or coworkers;

2. As part of the process of bookmarking sites and organizing them into "folders" users would be indicating a measure of quality and connectedness among the URLs;

3. Profit!

OK, step 3 was a little more complicated. But the essence was that we would use the personal-backup product attributes to create a public search engine and "discovery engine" (I believe the marketing folks wanted to use that phrase!) based on user bookmarks.

This really shouldn’t sound too different from what del.ico.us was able to do, and we had something like $13 million to play with to make it happen. Not to mention that there were others with the same idea. Remember Backflip? So (besides the money),why did we fail and del.ico.us and the other Web 2.0 companies succeed?

I don’t think it was that we were "too early" or that we got killed when the bubble burst. I believe it all came down to product design, and to some very slight differences in approach.

To start, we launched Blink with a bevy of marketing dollars and a message very much focused on the individual storage benefits. We were very successful at attracting users (at its height Blink has 1.5 million members, del.ico.us currently has 300,000) and getting them to import their bookmarks into our system.

What I find interesting about this pair of posts is the thought that a company that had 5 times the user base of del.icio.us could be considered a failure while del.icio.us is not. This makes me wonder what defines success here...That the VCs made a profit? I assume that must have been the case with the del.icio.us sale while it clearly was not with the original Blink.com service. Perhaps it's that the founders end up as millionaires? What ever it is, it definitely doesn't seem to be about users.

I tend to agree with Anil Dash, del.icio.us isn't yet a success except for being successful at making the founders and VCs a good return on their investment. If a service can grow to be 5 times as large and still be considered a failure then I think it is safe to say that calling del.icio.us a success is at best premature.

My question for all you budding entrepreneurs out there, what are your definitions of success and failure?