An introduction landed with an embarrassing amount of praise attached. I said I was flattered, then asked the person on the other side to tell me the truth about LinkedIn.
I have spent most of my career building startups and leading both technology and product. A couple sold. We took one public. Two or three went nowhere. That is a pretty wide range of meetings, mistakes, lucky breaks, and operating problems.
At Shutterstock, I built the team from three people to roughly eighty over five years. At Aaptiv, I built a team of roughly thirty from zero. I know what it feels like when everybody can fit around a table, and I know what starts to break as the organization gets larger.
I had always expected I might eventually spend time inside one of the giant technology companies. The resources are obviously more abundant. So are the layers. The question was whether modern tools and good management could preserve some of the speed and closeness of a small team inside a company with tens of thousands of people.
That curiosity sat awkwardly beside what I had been telling recruiters. I wanted meaningful ownership, the ability to change the business, and a genuinely interesting problem. I had already taken a company public. Another late-stage unicorn with a narrow job and limited upside looked like the wrong kind of unicorn.
Big tech was a different question.
I was talking with people around Facebook and Google, but logos were not the useful part. I wanted a first-hand account of the engineering culture at LinkedIn. What did the company actually care about? What was good? What was annoying? Could somebody who liked building from zero still have real impact there?
LinkedIn was also a funny one for me. I remembered the launch and being skeptical that it would go anywhere. I was completely wrong. It changed how people use professional relationships, then became part of Microsoft, a company and founder story I had always admired.
I asked for ten minutes with somebody who had actually built there.
No grand decision. No dramatic exit plan. I just did not want to dismiss a bigger company from the outside. The useful part was finally admitting I was curious.