business, venture capital, yahoo

Awkward Moments and Serendipity

I’m still learning about what it means to lead a life on the Web. When I least expect it, the ripples from the smallest actions seem to grow into much larger waves.

Here is an example. At the Web 2.0 Conference in 2006, there was a great “hack.” Internet industry players had gathered at the Palace Hotel in San Francisco. In addition to panel discussions, there was also an expo floor showcasing companies that had paid premium slotting fees to demonstrate their latest products. Typically the prices for a similar type booth runs in the tens of thousands of dollars. Not an easily afforded sum for a start-up – especially the earliest ones.

Not too far from the official expo area there was another “mini-expo.” However, it wasn’t officially associated with the conference. The story I heard was that the conference organizers had somehow forgotten to book / block this room. In their place, an early-stage venture capital firm called First Round Capital reserved the space and used it to create a more capital efficient “mini-expo” for their portfolio companies. Conference hack! As soon as I heard the story, I became a fan of First Round Capital.

Earlier this year, when Facebook introduced a feature allowing its users to become “fans” of companies, I was happy to show my support for First Round. Unfortunately, my support for them was about to make things uncomfortable.social ad

This past winter, after Microsoft announced an unsolicited bid to acquire Yahoo, Josh Kopelman of First Round devised a little experiment. The idea was to get a sense of what was going through the minds of Microsoft and Yahoo employees. Did the acquisition talk make them want to leave their jobs? Using Facebook’s social ads program, he created an ad (example to the right) targeted at both Microsoft and Yahoo employees, asking “Thinking of Leaving?” What Josh didn’t know (and what this example doesn’t show) was that these ads also included the profile pictures of people who had declared themselves to be “fans” of First Round Capital. Without me knowing, my picture was included in one version. Friends who saw it simply asked, “WTF?” Insert the awkward moment. I had no idea about what was about to begin.

I had no plans to leave Yahoo, and I certainly did not want to give anyone the impression that I did – my time at Yahoo had been among the most enjoyable years of my career. I had only met Josh briefly but I reached out to let him know what I thought of his experiment. He too was surprised to learn about the use of fan images in the ad. He immediately halted the test and issued an apology. Spooked by the incident, I removed all “fan” pages from my Facebook profile.

Meanwhile, my dialogue with Josh continued and we exchanged ideas on some of the opportunities and challenges presented by the new world of social ads. Eventually, we made plans to connect during his next visit to the Bay Area. That was in February. We’ve kept the dialogue going ever since. I’m now proud to say that this July, I’ll be joining First Round Capital as Principal in their San Francisco office. Serendipity.

I suppose it could be argued that these social ads wound up doing exactly what they were intended to do, but I don’t agree (besides a $0.05 CPM coupled with six months of dialogue is just not an efficient way to sell). Instead, two misunderstandings led to a dialogue. The first misunderstanding was mine – I didn’t know that by becoming a “fan” of a company that I was also lending it my likeness. Josh shared this misunderstanding and did not know social ads would use the images of his firm’s fans. To both of us, this was an unpleasant alarm of how much is still to be learned about this new medium.

In fact, this past Friday I heard these same alarms. Having already told my closest Yahoo colleagues that I had decided to leave Yahoo to join First Round Capital, I decided it was time to become a First Round “fan” once again. Then after I finished my last day at Yahoo, I joined the Yahoo Alumni Group on Facebook. Of course, these two items showed up in my Mini-Feed. What I never expected was that these two little items would be reported on by TechCrunch.

A second awkward moment courtesy of Facebook. Hopefully, this one turns out as well as my first.

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5 thoughts on “Awkward Moments and Serendipity

  1. Pingback: Redeye VC

  2. At least now you’ll know better than to become a “fan” of companies you want to invest in until you want that to be public knowledge. We’ll all be watching your news feed closely!

    Congratulations on the new job, new office, and new chapter!

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