Book: Flash Boys: A Wall Street Revolt

A cliche I’ve heard many times is “Wall Street Always Wins.” The first week of 2016 in the public markets has been an entertaining reminder of this.

In 1998, when I started ending up with lots of shares in public Internet companies, I came up with a formulaic approach for any public equities that are distributed to me (either from our funds or other VC funds). The approach was mathematic, dispassionate, and easy for me to execute. Over the past 18 years this strategy served me well.

In 2002, I decided not to own any public company stocks except for companies that I directly invested in as private companies. I sold whatever remaining public company shares I still had post Internet bubble and took an entirely different approach to the public markets.

While I have still have plenty of public equity, it is through either index funds, equity fund managers that I have a long term relationship with, or a few companies that I invested in when they were private companies. And, for the last category (the shares I own personally), I still use the long-term formulaic approach I came up with in 1998.

I’m a big believer in the Bogle school of thought about owning the market, rather than trading stocks. As a result, I don’t have to pay attention to the public markets on a daily basis. Or a weekly basis. Or an monthly, quarterly, or annual basis. Or basically, at all. That lets me focus all of my mental energy on what I like and what I think I’m good at (which is not being a stock picker or trader.)

The first finance course I took at MIT was 15.401: Finance Theory I and was taught by Stewart Myers. I remember the cover of the textbook, fondly called Brealey and Myers, what the Capital Asset Pricing Model is, and a few other things. Even though my future business partner Dave Jilk told me that he enjoyed the finance classes he had taken, I didn’t, and after taking 15.402 (which was required for my masters degree), I was done with corporate finance after taking the final exam.

Except – not really – since a big part of my job is corporate finance, just for startups and fast growing companies. However, unlike the evolution of the 15.4xx finance classes, and the extreme amount of financial engineering and financial innovations (both good, bad, and questionable) that came out of MIT research and MIT professors, most of the math involved for a venture capitalist can be done in one’s head, as long as you are decent at arithmetic.

But, for some reason, I occasionally like reading about Wall Street and corporate finance. Some of it is akin to watching the inevitable train wreck that surfaces in books like The Big Short. Some of it is to try to understand human motivation and behavior in a sphere that I don’t encounter often. And some of it is just to learn something that, in some parallel universe, I might be participating in.

Flash Boys was a good capstone to the last week of wallowing in the global financial crisis of 2008, which I began by watching the movie The Big Short. Once again, Michael Lewis took a hard topic and made it accessible, fun, interesting, and character heavy. After reading the book and then poking around IEX, the alternative trading system at the center of the story, I got a fun bonus by discovering that Spark Capital and Bain Capital Ventures are both investors in IEX.

I’m probably done for a while reading about Wall Street. But, once again, after reading Flash Boys, the cliche “Wall Street Always Wins” rings true in my brain.