Clippers Lakers Basketball

I had an economics professor who used to talk about the value of unique skills as a competitive advantage. He would use Kobe Bryant as a metaphor, saying “The Lakers pay Kobe Bryant because there are very, very few people who can do what Kobe Bryant does”.

I’ve been reflecting on that in terms of my career, and also because I’ve recently been working with some young people right out of school and looking to break into the startup scene. I look at the generalist vs. specialist debate from the perspective of my career, and also from the perspective of having to hire people at startups.

My Own Experience

I have always been a generalist. This was not a conscious decision. It was more a result of being  kind of geeky, a little ADD and not particularly sure of what I wanted to do when I grew up.

So, I’ve now held roles in marketing, product management, UX research, strategy, business development, sales and bartending.

I can say without question that I would have risen faster from a career standpoint if I had specialized in a functional area. Working in early stage startups, I’ve been able to get by because I’ve learned a lot of ways to add value to an organization, but I suspect I’ve also been pretty lucky and have a tendency to out-grind people.

As A Hiring Manager

Most of my experience hiring has also been in early stage startups. I’ve been in a half-dozen environments that we’re ‘in utero’ in terms of their  infancy. In all of them, almost without exception, I would prefer to hire people with some type of domain expertise rather than a ‘jack of all trades’ employee who I can put on anything.

Here’s my advice if you want to work in startups:


You can always go more general. Getting specialization as your career advances is significantly more difficult. I suggest that young entrepreneurs get great at something and be able to deliver in a functional area. Learn to code front end, learn BD or acquisition marketing, get your design on. The idea that specialists can’t run companies is a complete myth.

Go Work For A Big Company To Break Into Startups

If you’re out of school and you want to get into a great startup, you should consider going work at a big name brand company and get some functional specialization or a year or two.  Why?

  1. You can add a name brand to your resume. This matters when you’re raising money or trying to work at a startup. People will tell you it’s not important but it matters.  The girl who worked at Google out of school is going to get funding over the exact same person who worked at a failed startup out of school.
  2. You’ll get a structured process for skill development. I realize that there are a ton of online tool for learning skills, but the structure and process that big companies place on employees can actually be pretty beneficial when you’re just getting out into the world.
  3. It’s easier to go from big to little than little to big. It’s hard to spend ten years in early stage start ups and then get a job at Bloomberg.  It’s far easier to spend 2 years at Bloomberg and get a senior role at an early stage startup [or raise funding] because of your functional expertise and the brand on your background.