When It Comes to Gambling on Investment Apps, the Sucker is You

If your investing app is offering you the chance to bet on sports, you might like to know what the person on the other side of that gamble thinks of you. For professional bettors like Chris Dierkes, you're the dumb money.

I don’t want to compete against the smart people, I want to compete against the dumb people. What has the highest-volume markets in Robinhood is going to have the dumbest customers. And that’s where I want to be.
— Chris Dierkes

Dierkes used to work in finance but found that he couldn't compete against big investing firms in the options markets.

Now, he is a pro sports bettor who can have $1 million riding on any given day's sporting events. In this world, his resources and expertise give him an advantage over regular folks putting $50 on their favorite team.

The number of people gambling within their investment apps is rising. On the Robinhood app, they wagered $2.5 billion in October of 2025 alone.

Dierkes' counterparts in his wagers are so unsophisticated that they don't check to see what odds are being offered on other platforms. As a result, he can boost his returns by offering unfavorable terms.

In this new world, investors might want to remember some old advice. It was Paul Newman who said, "If you're playing a poker game and you look around the table and and can't tell who the sucker is, it's you!'

Disclaimer: This newsletter is for informational purposes only and does not constitute financial advice. Please consult a qualified financial advisor before making any investment decisions. Links on this page may be affiliate links, meaning your purchases help support this newsletter. Quotes may be edited slightly for clarity. Images represent our best effort. Copyright © 2025 mydailyoracle.com. All rights reserved.