“I will say that a lot of tension arose from Googler’s expectations that the company’s culture had to be exactly the same as what it was when the company was one fifth the size” Former GOOG & MSFT executive (and multiple time founder) Javier Soltero on Career Advice, Big Company Culture, and Startup Hiring Tips

I am reluctant to call someone a ‘friend’ unless the relationship has crossed the threshold honoring the depth of commitment behind the designation. By that framework I started out as a ‘fan’ of Javier Soltero way before we became friends. It was his mobile productivity startup Acompli (later acquired by Microsoft) which first caught my attention. The state of email and calendaring apps at the time was depressingly basic despite the importance of them in day-to-day work, so I was an enthusiastic adopter of whatever developer was building for power users and not simply ‘making an app version of the existing web interface.’

Our journey from ‘fan’ to ‘friend’ had a substantial time lag — an intermediate period of friendliness — but I’m comfortable we moved to the F word a few months back after a nice walk in Marin. It was our first time outside of DMs, emails, texts, and we learned a lot more about one another. That increased my desire to continue probing, and, share it here, via Five Questions. There are some real gems about technology careers, entrepreneurship, and so on. Enjoy!