Why I Invested: A Series on Early Stage Angel Investing

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Over the last 8 years since my first software company, TalentBin, was acquired by Monster Worldwide, I’ve become a fairly frequent angel investor.

I’d love to say it was because I thought it was a surefire path to financial improvement - but the actual truth is that I find it quite intellectually compelling - combining problem solving, leveraging existing expertise, learning new things, and other things that I consider best in life. So I’ve probably ended up doing more than was probably wise.

Over the last nearly decade I’ve invested in north of 100 individual companies during my nights and weekends, and have certainly learned a lot along the way. And not done terribly at it either, with a handful of 20x realized outcomes, and even some 50x, 100x and even 500x markups (fingers crossed!). Not to mention, of course, a good number of investments that have gone to zero.

But despite this effort, I’ve never done any writing about it. Probably has to do with an all-consuming day job. So I thought I might change that up a bit.

The goal of this series is to write on why I invested in a given company as a mechanism by which to demonstrate (and clarify? Lol) my thinking to help others who are thinking about doing the same. (Not disimmilar to why I wrote Founding Sales!)

I’ll probably start with companies that have exited or have reached substantial escape velocity, and then later on move into companies that are earlier in their journey…and maybe some of the ones that didn’t work out as well.

Individual Investment Posts:


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