I am often asked about how many investments I’ve made and I surprise them by the number I have made in such short a time. I too think I went out too fast as a budding angel investor but, looking back, I think ultimately this had many advantages, some of which were not obvious to me until I did it.
The obvious disadvantages are that I had allocated a portion of my personal savings to do this, and I ended up deploying almost all of it in 2 years! This unfortunately meant that I had to slow down dramatically the number of investments I do from now on, and potentially ratchet down the size of investment into new companies.
The obvious advantages of going wide are that you spread out your risk, just like diversifying your investments in your personal investment portfolio of stocks, bonds, etc.. Putting your eggs in one basket, or a few baskets, increases your risk of losing it all no matter what you put your money in.
The non-obvious advantage of going broad was the knowledge I gained from exposure to different companies and their personnel (and their personalities!), their products, their struggles and solutions.
I always knew I had ADD, and that I enjoyed working on multiple products. In my old position as head of user experience at Yahoo!, I could satisfy my ADD tendencies towards getting my fingers dirty in a variety of projects, and learning about many others. After I left Yahoo!, I wondered about how I would provide an outlet for my ADD-ness and orchestrated a solution through angel investing. By investing in many companies and becoming advisor to them, I was able to continue to satisfy my Internet ADD.
However, being exposed to so many products and projects also allowed me to see across many different products and be able to connect them in ways I would never have been able, had I not had access to the depth of information in each product. I was able to see synergies and feed my creativity, which allowed me to come up with ideas that would not have come to light without the broadness of depth of information (if that made sense). I had always been a big believer that creativity can be enhanced with more information (but also knowing that creativity can often be reduced because you get bogged down by knowing too much) and this was further proof of my belief. Working on one or two projects would never had given me the insight that I can see now. Also, if I was not advising and/or investing in these companies, I would not have gotten the depth I needed to be truly successful.
It was an non-obvious result of the diversity of my investments that I would be a more effective advisor to internet startups. My broadness of vision across many different products and projects means I can bring creative proposals to time starved entrepreneurs whose myopic but necessary focus on their own projects sometimes prevent them from seeing the wide view and potentially better alternative paths and solutions.