The People Problem

The People Problem — Introduction

I reached a significant milestone in life on my last birthday. I have now lived more of my life as a working professional than I have lived as without one. I don’t know if that means something, but I now find myself in more situations where I can find similarities in a current event with something I have experienced in the past. I suppose that is what “having experience” means.

Talking about experience, most of mine has been in almost every element of creating and operating “startups” as defined in the traditional sense. I started my career as an intern at one of Silicon Valley’s most well-funded startups. I spent majority of my days there learning how to make a good cup of coffee and playing video games. My first “real job” as a software developer was when I didn’t know the things I was expected to have known and learned before showing up for the job; and instead of kicking me out the door, I was given the freedom to learn and produce good work. I have gotten jobs well below my skill levels and way above my skill levels. I performed well in places where I should have failed, and failed miserably when I should have killed it. Throughout my professional career I have been dreaming up ideas, building prototypes, forming companies, creating products, growing teams, getting hired on teams and getting fired from teams.

I was hoping that having all this experience meant that I am more likely to know how to solve problems that I need to solve to do my job now. For every “problem” that I now face, I can look at the situation, analyze the information and match it to a pattern from my past experience.

Unfortunately it’s not that simple. Call me naive, but I have learned that the most important variable in any challenge that I come across around “work” (startups, companies, businesses, side hustles, weekend projects, and the myriad of things we call “work”) is always the same one: people. Good work happens because of people and despite of people.

It’s a people problem.

Welcome to ‘The People Problem’. My goal here is to share things I have experienced, observed, and learned about creating and growing companies. The underlying theme of these observations is around the thesis that people involved in companies are the reason why companies do the things they do (or don’t do they things they don’t).

Follow along at, and share your thoughts/questions/ideas/comments with me at

While you wait for the next post, here are some resources that I am learning from and getting inspired by these days: