A cool and candid post-mortem from the founder of Gowalla

This piece by Gowalla founder Josh Williams in Medium.com is a great recapitulation of the "check-in wars" from 2008-2011, when location based services like Gowalls and Foursquare emerged (to be joined by Facebook) and fought to establish this new turf in the online world. Gowalla was a casualty of this war, and Williams' candid recounting of the story is a service to other tech entrepreneurs. While he doesn't directly deal with mistakes that contributed to Gowalla's downfall, the story helpfully lays out the extreme uncertainty that comes with any new venture (especially online ventures). Here's a taste:

In one of the many highlights of Gowalla, we crafted an amazing tie-in with Disney that was loved by both our community and theirs. Each of these endeavors cost us time and money. Unfortunately the relative payoff for us was simply less due to network effect.

While Gowalla continued to grow, the trajectory was not what it needed to be. At least not in terms of winning the game we had chosen to play.

We were the younger, prettier, but less popular sister of Foursquare. And even that had changed. In time, Foursquare had dramatically improved the design and experience of its service. This was no longer a defensible platform for us as a company.

Around this time we knew that our path was in trouble.

From Fred Wilson: a visible reminder of a past mistake

This was originally posted on Fred's AVC blog on May 24, 2011:

Longtime readers know that I'm a bit obsessed with worthless stock certificates. I like to keep them around and displayed so that I see them on a regular basis. They are a reminder that we make mistakes in the venture business. I think it's a good idea to remind yourself on a regular basis (particularly when markets are like they are now), that everything you touch doesn't turn to gold.

We are moving our offices upstairs to a new office and we've spent a fair bit of time this week cleaning out old files. I came across a big stack of worthless stock certificates from the Flatiron Partners portfolio and thought I'd share one of them with all of you.

 
Kozmo was a decent idea that actually worked in NYC. But in the mania that existed in 1999, the company raised hundreds of millions and went on a spree opening up something like 18-20 cities. That expansion was largely unsuccessful and the result was that the company went under. We lost our entire investment as did all the other investors.

On a week when we are celebrating lots of good news in the Internet world, I think its useful to also remember what didn't work and why so we don't repeat those mistakes.

Some of what Fred is referencing in "good news in the Internet world" would include LinkedIn's IPO, which rose 80% above the offering price on its first day of trading.

Here's some more info on Kozmo.com if you're interested.

The principals dissect the failed AOL-Time Warner merger, 10 years later

The most powerful lessons can be learned years after a mistake is made. This is especially true with a colossal failure. Only after much time has passed can the people involved shed their self-protective impulses and see clearly what happened.

There has been much written (for example here and here) about the 10th anniversary of the failed AOL-Time Warner merger (AOL again became an independent company in mid-December 2009). But nothing has been as compelling and rewarding to read as this New York Times article recounting the history of the merger from the viewpoints of the principal actors involved. Did you know that TW CEO Gerald Levin and AOL founder Steve Case first met at the 50th anniversary celebration of the People's Republic of China? I didn't either.

Once back in the States, Case began his pursuit:

MR. LEVIN We’re now back in the United States and I think Steve Case called me on the phone and in that conversation more than alluded to putting the companies together. I had my traditional script and quasi-legal background that when someone calls you on the phone, make sure they understand you’re not for sale, which we certainly weren’t, and decline any overture, which I did over the phone.

And the story goes on from there. It's riveting, candid, and revealing, and a must read for anyone who is eager to do a big merger. It might make them stop and think a bit.