1:1 exec coaching: I coach a small number of senior product leaders — usually people stepping into bigger, more complex roles or working through change. If that’s you or someone you know, ping me.
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In early 2006, I was working at Yahoo!, back when it had the largest audience on the web. It was a great place to be working as a product person in tech.
I had just moved to a new “startup” inside Yahoo!, building a new service to compete with CNET. My career was going well. I’d recently been promoted to Director.
A friend of my former manager Chris called me one morning with an opportunity.
I still remember doing the phone call from inside one of those small phone booth rooms on the old Yahoo! campus. The guy got right to the point.
“Hey, good to connect,” the guy said. “I’m at this video startup. It’s taking off, video is hot, and we’re doing well. We’re hiring our first product person, and Chris says you’re great at product and would be good to talk to. Would you be interested?”
He even told me a few of the video competitors at the time. “I realize there are like 13 video competitors now, but this thing is working well,” he said. I quickly looked some of them up on my laptop while he continued his pitch. Vimeo, Dailymotion, Metacafe, Revver. Plus a few others. Crowded space!
Then: “We don’t have an office yet, so we’re working out of our VC’s space on Sand Hill. We could meet there.”
I said something like: “I’d love to meet you but I’ll be honest. I’m doing pretty well at Yahoo! I just got promoted. It’s probably unlikely that I’d move. I’m really not looking.”
I never heard back. When someone at one of those super-fast-growing startups is hiring, they move on quickly if you show any vibe of hesitation.
We launched “Yahoo! Tech” that May. Newsweek said it might “portend what the media will look like in coming decades.”
That little video startup? It turned out to be YouTube.
Google bought them in October 2006 for $1.65 billion.
Fuck.
Right?
Yes and no. I looked at a future door using too much present tense data.
Though at the time this felt like a miss, the path I ended up on opened up new doors that affected my life in ways I couldn’t have imagined.
I definitely take more coffees, say yes more often, and explore new things instead of defaulting to being satisfied. That’s lived on for me as a lesson.
But I also went on to work at companies and meet people, both of which compounded into interesting roles, relationships, and fun. For example, someone I met at LinkedIn later connected me to Included Health.
It all ends up working when you zoom out and just keep moving.
Every decision or choice simultaneously closes off opportunities, but also creates new ones. If you take advantage of the new ones, missed ones don’t turn out to be so bad. They’re learnings.
Oh, and always take that coffee.