One of my favorite things about being a startup investor is learning about all sorts of new things. The first is about the investing business itself – I can safely say that I’ve only touched the tip of that iceberg for sure. The second thing I learned was much more broad.

Actually the second “thing” is really “things” plural.

As most people know, I invest typically in all things internet. I am fortunate that I worked at Yahoo! where we worked on a pretty broad swath of things, and I’ve had exposure to a multitude of products and services. As head of user experience and design, I oversaw a lot of it and learned a ton about a lot of things, becoming a jack of all trades of sorts. Even then, there were many things we didn’t do. When I started investing, I found my broad exposure very valuable both to me as an investor, and also helpful to entrepreneurs as I could tell them all the good and dumb things we did at Yahoo! in those industries. But then, the internet filled up with the usual stuff.

Now I’m looking at stuff I know little about, or nothing about!

Some things I’ll never get into – personal resonance is still very relevant and important. For others – there could be something there… it would also mean a lot of effort and time in learning about the business, industry, its customers, everything about it I can. Enough to be an expert maybe, certainly enough to be dangerous!

I get extreme joy when I learn about some area I know nothing about. I look stuff up in books and on the internet, I talk to experts, customers, advisors, and others in the industry. I may even visit places where the product is sold, or where the pain point is felt. My team’s research department pulls up every shred of info on a subject and I devour it all.

Then, this is most exciting to me – making a monetary bet in that area in a company and knowing I made the right call if it exits. Unfortunately, the chance of a successful exit is pretty low at early stage but I am still left the knowledgeable I’ve gained which is satisfying and, I’m sure, will prove useful in the future.

There are many in my field who say to never invest in anything you know nothing about. I would say that is true, except that it leaves out the part about going out and learning about that thing that you knew nothing about. It is disheartening to see that many investors stop learning or become lazy and lean on others’ expertise.

To me, becoming a jack of neverending trades is one of the best things about being a startup investor.

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