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I wanna be like Kev: Unpacking Digg’s complicated legacy

kevin rose digg ceoLast week’s sale of Digg for a paltry $500,000 closes the book on what was once among the most inspiring stories in Silicon Valley. It is impossible to separate Digg’s legacy from that of founder Kevin Rose. With the benefit of hindsight, it’s clear that Rose had as much to do with Digg’s failure as he did its success. That makes his legacy a complicated one.

Digg’s early promise

Digg provided one of the most inspiring startup creation myths in history. Kevin Rose had an idea for a website. He hired freelancers to build the first version of the site, paying each $12 an hour. He paid $1,200 for the Digg.com domain. Fast forward 18 months, and Rose was on the cover of BusinessWeek, having “made $60 million in 18 months.” The numbers may have been inflated, but the excitement was very real. In less than two years, Rose had moved from idea, to product, to stardom.

old digg screenshot social news

And what a product it was. Digg addressed one of the Web’s key problems: How to find what is interesting and novel in a limitless sea of possibility. Curated aggregators like Fark and Slashdot could go only as far as the capacities of the curators allowed. To exceed this limitation, Rose tapped the wisdom of the crowd to “digg up” the best stories online. This idea, combined with a design aesthetic that was always at the forefront of “Web 2.0,” created one of the most important startups of its era. It also created, in Rose, a new aspiration for a legion of 20-something nerds: “technologist as celebrity.” In the era of Entourage, “tech startup founder” seemed to be as good a way as any to acquire the millions of dollars each of us felt we were due.

I was one of those nerds. In 2007, I wanted to be Kevin Rose. Today, however, both Digg and Rose have greatly declined in prominence. Rose’s on-again off-again relationship with Digg is to blame. This lack of focus means reconsidering the praise with which he had previously been showered.


Hot on the heels of Digg’s ascent to prominence came Revision3, which assured Rose’s continued ascent to fame. Revision3 was founded in 2005 by Rose, and, among others, Jay Adelson — then CEO of Digg. Though not tightly related to Digg, it did provide the means for Rose to produce the video podcast Diggnation, on which he and co-host Alex Albrecht recounted Digg’s stories from the previous week. This gave unique incentive to Digg’s users: The right story could land them air-time on one of the most-watched video podcasts of its time.revision3 kevin rose digg

It also provided a platform for Rose’s personality, which was far from the traditional conception of a CEO. Rose was undeniably cool, with the laid-back confidence of a person who had made it. Diggnation itself seemed cool as well — at least to my 23-year-old self. With drinking (sometimes to excess), swearing, and foul humor, Diggnation appealed very strongly to me. It appealed to legions of others fans as well, as demonstrated by the podcast’s many well-attended live events. However, Rose wasn’t finished creating new products. His passion for “new” would continue, and would continue to be a distraction from Digg.

Pownce and other distractions

First among these was Pownce. Essentially a souped-up Twitter, Pownce launched in late-June 2007 and was founded by Rose, Leah Culver, and Daniel Burka. Eighteen months later, Pownce would be purchased by Six Apart and shuttered due to a lack of growth and revenue. This wasn’t just a distraction to Rose, but also to Burka, who was one of Digg’s top designers at the time.

pownce microblog twitter kevin rose social media

Rose’s fascination with Twitter continued with WeFollow, a Twitter directory Rose launched at South by Southwest in March 2009. Though later acquired by Digg (for some reason), WeFollow was of such minor prominence that it lacks even a Wikipedia entry to remember it by. Its chief feature, as reported by CNET’s Harrison Hoffman at the time, was “the unique advantage of Rose’s star power.” Not much to show for such a major distraction from Digg, which employed Rose at the time, and which had threatened to fire him if he continued such distractions.

Then came Rose’s career as an angel investor. Having taken millions off the table during Digg’s later funding rounds, Rose began to put that largess — and his near-peerless social graph of the Valley’s best and brightest — to productive use. Today, Rose’s portfolio reveals a rare talent for investing, and lists holdings in Twitter, Zynga, Square, Foursquare, Fab, and Path amongst its assets. However, this wasn’t without cost to Digg. As Rose’s interest in investing grew, his interest in Digg waned.

Rose would return to Digg full-time as CEO in early 2010 in an attempt to save the company, which was now floundering. However, he gave up this role just six months later as a new CEO was installed. Rose’s work resulted in the ill-fated Digg 4 redesign. Plagued by launch difficulties and departing significantly from the site’s earlier methodology, Digg 4 would be the final nail in the website’s coffin as Reddit began to dominate the space.

Though a visionary founder, Rose’s uncommitted relationship with the company may have been Digg’s undoing. Even when with the company, Rose’s attention was often on other new ideas. After such a promising start, Digg’s story today is one of squandered potential. This casts Rose in a far different light than when he graced the cover of BusinessWeek all those years ago.

Kevin Rose today

The dream of the startup founder is still very alive today. The continued popularity of Jason Calicanis’ This Week in Startups demonstrates the continued fascination with rags to riches stories in tech. However, Rose is no longer the figurehead of that dream.

Facebook has become the premier entrepreneurial story of our era, and Mark Zuckerberg may be the most well-known CEO in the world. Facebook’s ubiquity today can be attributed to Zuckerberg’s leadership as much as anything else. From all accounts, he works tirelessly on a singular focus: pursuit of his vision for Facebook. This is a stark contrast to Rose’s serial entrepreneurialism. It also supports a lesson I learned from This Week in Startups during my days of startup mania: Having an idea is nothing, how you execute on that idea is everything.

As for Rose? He’s still way ahead of the game. Rose founded yet another startup, Milk, in early 2011. This team released one application, shut that app down less than a year later, and then was acquired by Google. Today, Google has Rose working for Google Ventures, the company’s VC fund.

Today Kevin Rose is a millionaire VC with nearly unmatched connections in the Valley. He has a proven ability to bring products to market. If he has new ideas, he has the skills and VC connections to make those things happen. We may not have heard the last of Kevin Rose.

So, in 2012, I guess I still want to be Kevin Rose. But I’d rather be Sean Parker. Why not Zuckerberg? Come on, Parker is so much cooler. Sean Parker is so cool that Justin Timberlake played him in a movie and still wasn’t as cool as Sean Parker. We should put him on a stamp, or something.

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