Generalists rules

Is it really better to be a specialist? Or will the future be built by generalists? I think it depends on a few key factors…

A couple nights ago, I was at a founder dinner talking to a FinTech expert with an impressive background.

For 15 years, he worked at a major retail bank in their FinTech division leading projects and developing new technologies across several key business units.

After a decade and a half of working in a single industry with a single focus, he was now an expert at the top of his field.

I can’t lie… Sometimes, I envy that.

On one hand, I wish I had more singular experience in my career. There’s a compounding effect to the effort, expertise, time, and pay.

But, my career has followed a much different path:

- I worked for a year in retail store leasing and an additional 10+ years in commercial real estate buying and managing multifamily apartment buildings

- That led me to spend four years building a PropTech startup (which first exposed me to the idea of ‘Venture Capital’ and led to my first angel investment in 2014)

- I helped start a traditional real estate investment and property management company

- I spent a few years building a full-service marketing agency with my brother

Even though I had been angel investing for six years before this, I only started FULL-TIME as a Venture Capital Fund Manager about 4 years ago.

It’s easy to occasionally feel like my career path has been completely disjointed. But, the benefit is that it has exposed me to SO many different industries, people, and businesses.

As a result, I can now sit down with almost anyone (like, say, a fintech expert working at a major retail bank) and have an intelligent conversation about their work.

As an early-stage investor, it’s better to have a wide breadth of knowledge because your success is based on your ability to evaluate PEOPLE, not products.