i-c584caecfa56f35d908efd6b1859a00c-Scoble at Le Web.jpg
Robert Scoble at Le Web

As a journalist covering a particular business, there is a temptation to believe that we know enough about that business to actually become a full participant in that business. We have been writing about it, we see what works and what fails, so we should know enough to try our hand at it too. But more often than not, we don’t succeed.

The latest example of that came from popular tech blogger Robert Scoble, who left his cush gig as Microsoft evangelist to be a videoblogger for startup PodTech. While Scoble might not qualify as a traditional journalist, he fits in the mold of someone who was writing about the media revolution around him — on his blog and in the book he co-authored, “Naked Conversations” — and felt he knew enough to take the chance on a startup. Now he is leaving PodTech as it struggles with a new business focus, and he might end up at Fast Company, according to TechCrunch.

Other writers and journalists have tried and failed, most notably during the dot-com boom times. Back then, even CNN anchor Lou Dobbs left the network for the startup Space.com before returning to CNN. And yes, I caught the fever and worked at email newsletter startup Topica back in 1999 and 2000 before returning to freelance writing. More recently, blogger-journalist Dan Gillmor left the San Jose Mercury News in late 2004 to help start citizen media site Bayosphere, before that venture failed.

So what’s the big draw to the startup world? As Gillmor told his colleagues, “I am jumping off a cliff with the expectation of assembling a hang-glider before I get to the bottom.” Even though he didn’t get to assemble the hang-glider in time, Gillmor did land softly as director of the Center for Citizen Media and now a founding director of the new Knight Center for Digital Media Entrepreneurship at Arizona State University.

For me, I was drawn to the idea of going to a tech startup to see how such a company operated from the inside. I had actually briefly been at an earlier pre-Internet startup called MusicNet in 1993. Startups mean that you’re in on the ground level, not only with the chance to shape something special but also to profit if and when the company becomes successful. It’s part of the American dream to help start a company that goes on to revolutionize its field, as Google or Microsoft have done.

Of course there are many journalists who have succeeded in creating online businesses based on their writing. Rafat Ali has been successful with PaidContent and its network of sites, while OJR’s Robert Niles points out that Josh Marshall at TalkingPointsMemo and Markos Moulitsas at DailyKos have built businesses around their political blogs. But that seems to be a different animal than actually building a startup around something other than your writing, as Editor & Publisher’s Steve Outing did with his recently failed Enthusiast Group.

Knowing Less Than We Think

Perhaps the problem is that we think we know more than we do. I can’t speak for other journalists or bloggers who have made the leap and failed, but I can say that the odds of a startup becoming an iconic company — or even a profitable one — are pretty slim. Topica is one of those rare dot-com startups that has actually survived to this day, though it hasn’t lit the world on fire.

Going back to Scoble’s old 2006 blog post, in which he described why he left Microsoft for PodTech, helps give some insight into why he jumped ship at the time:

Yesterday I was talking with Amanda Congdon, one of the co-founders of Rocketboom. Her videoblog is now seeing about 300,000 viewers a day. That’s, what, a year or so old? Did you know that advertisers are now paying her $85,000 per week? That’s almost as much money as I made in an entire year of working at Microsoft.

Now, I have no delusions that I’m either Amanda or Cali [Lewis of Geekbrief.tv]. I’m not half as cute as either of them, for one. Nor am I as smart. Or as visionary. I’ll just have to work harder (which is going to be very tough, since Amanda tells me she and her team are working nearly around the clock right now to put together their three-minute videoblog).

But I had the same smile on my face when I told Cali I just quit my day job too to work in this new media industry.

Yes, there’s a certain excitement, a certain freedom, a certain thrill in jumping off that cliff with the hang-glider still being built. As writers and journalists, we are constantly viewing (and reviewing) the world of other people, the real doers and shakers who are changing the world. We feel like our own fame and respect is built on the accomplishments of others. We might bring an important story to the public’s attention, but it is rarely our story.

Going to run a business or work at a startup gives us as writers a chance to be part of the story, and not someone who is merely latching on to someone else’s story. But in that process, that excitement, we can also lose sight of who we really are, what we really know. At Topica, I realized that being at a startup could be a lot of fun, a lot of hard work — and also a loss of personal identity. I had to put my own creativity into the context of the business, and it had no validity on its own.

But trying and failing is not necessarily a bad thing. Gillmor counts his lessons from Bayosphere as some of the best of his life. I’m sure Scoble wouldn’t trade in his time at PodTech doing videoblogs for anything else. And I’ve got notebooks full of hilarious notes taken at Topica company meetings for a future TV sitcom.

Journalists and writers will always be lured into the world of the businesses they cover because they will want to try it out in the first person — succeed or fail. But they should just consider the shoddy history of those who’ve done it before they make that leap into startup land.

What do you think about journalists that go to work at startups? Have any succeeded spectacularly? Would you consider making that step, and why or why not? Share your thoughts in the comments below.

Photo of Scoble by Mathieu Thouvenin via Flickr.