What I Wrote About Modern Investing Before Robinhood, Wall Street Bets, and Polymarket

I am looking back at old posts I wrote and taking the time to compile them here on my blog. The most interesting insights is how in many cases I had the right thesis or idea, but did plan correctly for the ultra long-term such as 10+ years from the time of the thesis. For example, I found this post that I wrote in 2016 about the rise of the modern investor.

The Future of Financial Markets is in a Hoodie

“Kenny Powers is a man. Kenny Powers is an athlete. Kenny Powers is a lover. But the most he is, I mean, the thing that Kenny Powers is the most, is a goddamn champion.”

Investing has long been surrounded by an image of men in suits. Big resumes and perfect business cards. You know what I’m talking about.

Hello, sir, may I look at your discounted cash flows and adjust them for my inflation forecasts which dynamically adjust according to the Federal Reserve’s interest rate mandate?

Of course! You can even see my weighted average cost of capital while you’re at it!

I think this is all going to change. Or it’s already begun.

Maybe it’s the connectivity. In a past life, you only heard stories of Wall Street “pros.” Or word of mouth stories about “trading desks” and “hedge funds.”

Today, we can meet investors who are farmers, surfers, skateboarders, and basketball players with just several taps. The diversity of investment background and interests is all here, online. With that, a cultural revolution is happening.

I think of it as a form of punk rock investors.

The best investors and market thinkers I’ve come to know are nothing like the movies. A very good friend of mine could analyze a company’s balance sheet and income statement better than any machine model in existence right now. He still does kick-flips on weekends.

I am fascinated by this change.

There are also more women coming into the investing world. Perhaps they’ve always been there. But now, just maybe, because the Internet is an open platform for all voices to be heard equally, they are really emerging and growing. Nothing can stop them.

Patrick Bateman, Bud Fox, and the characters that made markets and Wall Street a thing are falling apart. Throw in the images of Gatsby, too.

Two people walk into a room. One of them is wearing a suit with a tie and giant watch while the other is dressed casually. Maybe a t-shirt or a business casual look. Throw on some super chill sneakers. In this room, sitting at a table, is a young person tasked with picking one of these people to assist them with investing. This person knows nothing about either. Only that they are the same age and have similar experience.

Who will the young person pick based on dress code alone?

The financial crisis, student loan debt, after a string of bad publicity, and after the sweeping force of tech and its culture impacting every industry, the traditional look is turning into a sign of distrust and how things were done in prior years.

Throw in the vanity of Instagram accounts, the wannabes, the ones hi-jacking this old look. Showing you their private jet because, of course, they’re so good. What was that Matthew McConaughey line? Fugazi.

It’s an atrocity, really.

The fakeness.

The key, the absolute key, is knowing how to avoid the scammers, shills, and charlatans. That’s lesson number one. It took me years to figure that out.

Going forward, the do it yourself investor should only get more popular. It will happen overtime as those who previously were intimated by the imagery of “investing” come to learn that they have a phone attached to them at all times and they have access previous generations could not fathom.

Go ahead and try it. For those of you who are investors, go ask your friends about the stock market. Ask a rookie or a newbie. One of the first emotions they’ll experience is fear. Not fear that the market could crash right away. But fear of not knowing what to do at all. If you can break that barrier, the game is over. You win.