Ten Years Later

I have been on the phone a lot today—talking to Katie Fehrenbacher, Stacey Higginbotham, and Chris Albrecht. Surj Patel popped into town, and we had coffee. Call it kismet—or just coincidence—that today happens to be the tenth anniversary of one of the most terrible days of my life: I had to shut the doors on a business that carried my name and, for a while, I thought was my legacy. I loved it so much that I still joke that dating someone was cheating on this thing. I woke up thinking about it, I went to sleep thinking about it. 

So, turning off the lights in the office and pulling the proverbial shutters down one last time was hard. And so was writing a blog post announcing GigaOM’s demise. 

Everyone had their say. Many former colleagues had a chance to express their disappointment with the outcome. My loss was simply mine. No matter what I did, it was hard to truly banish the negativity from my mind. No one quite understands the deep, profound sadness of laying to rest something that is part of your very being.

My good pal, Tony Conrad, pulled me aside and told me that you don’t get over a loss such as this overnight — it takes a few years. Three years, at the earliest. And perhaps longer than that. And he was right — after three years, I realized that I was moving on. By year five, I knew I had become a better person by failing so spectacularly, so publicly. It has made me a better investor, and even that chapter has come to an end. More importantly, it made me realize that sometimes you have to look beyond the outcomes to really see what you gained and what you’ve lost. I stopped even thinking about the past and even the day. 

Today, however, I woke up pretty early and somehow knew it was ten years later. The cosmos was reminding me of how far I had come. As the day comes to a close, I am sitting here reminiscing about the past—and all I can think of are the people who came together, the earliest believers, and how successful they have become over the years. When I see their bylines, I feel parental pride. That’s when I miss them. 

In time, what were wounds have become battle scars to be cherished. The colleagues have become friends. They have grown, and ten years on, I feel a degree of intellectual satisfaction from having worked with them. 

Things we experimented with—paid subscriptions and events, for example—are now par for the course for most media companies. Whether it’s Politico, Axios, or The Atlantic, they follow the multiple revenue stream path. What we wrote about in the early days—ubiquitous connectivity, the future of work, cloud, data culture, clean technology, and cord-cutting—are now ground truths of our modern lives. 

It wasn’t a great outcome for my investors, and in hindsight, I suspect that as a media company focused on analysis and events, we could have been more cautious in our approach to business. In other words, pursuing big venture dollars pushed us in directions we didn’t need to go. 

Looking back, I realize I wasn’t the best of managers, and I have learned from that by becoming more open and by listening more. Failure taught me the necessary empathy towards other founders, mostly because in the end (unless they are psychopaths), they are trying their best in an imperfect situation for a perfect outcome. 

The end gave me an opportunity to start afresh. My romance with photography was kindled days after the shutdown. Photography has allowed me to discover a new meaning. In a decade, I have learned to hear the light and see the wind. I have communed with snow and reveled in silence. I have come to respect the slowness of time in the age of the network. A long time ago, I wrote, “Out in the field, walking into the wild with my tripod and my camera, I slowly transitioned from being lost to being lonely to being alone. And thus came the rebirth — both of the soul and the mind.” 

The change is not just in me, but in the world around me. The tech industry has changed, and so has the media. It is not just traditional media, but also blogs that have been superseded by new media approaches—podcasts, video, and short-form social media. There has been a higher abstraction of technology, and perhaps that is why there is less demand for my kind of journalism. 

The spectacle of technology has become more than the technology itself.The outsized success of technology means there are only two approaches to media — either be a supplicant and lay prostrate in front of the false messiahs, or be antagonistic towards those who have succeeded wildly. 

I have been fortunate that I don’t have to endure either of the two approaches. What happened a decade ago has saved me from the daily ignominy of being a tech journalist. Again, a reminder: what seems to be the worst event in your life is simply a journey to a better future. We just don’t know it at the time. 

I have started working with Fred on CrazyStupidTech, writing about things I like to write about, with open-eyed optimism and a belief that no matter what they say, technology is inevitable. We just need to work hard to get the best out of it. If there is any desire left, it is to host an event or two—small, intimate, and fun. But even that is for feeding my brain, not as a business. 

Thank you for being a reader all these years!

March 11, 2025. San Francisco