Hi Playmakers,

Have you noticed how over the last few years, online gambling has completely exploded? I remember a time not too long ago in a more innocent world where gambling was relegated to Las Vegas and a few key, physical destinations around the US. Today is seems like everyone is gambling on everything, from sports to weather.

With the prediction market alone making $17.49 billion in 2025 and expected to balloon to $100.4 billion by 2034, this really begs the question— how did we get here?

Before we dive into a history lesson, I know what fans of the industry are going to say, “but Jenny, sports betting and prediction markets aren’t the same thing! Sports betting is gambling on games, but prediction markets are all about trading contracts on real-world outcomes. One is gambling, the other is price discovery!”

Sure. Structurally they’re different, but the behavior is the same: you’re betting on outcomes.

Back to history. In 2018, the Supreme Court repealed the Professional and Amateur Sports Protection Act of 1992 (PASPA.) Effectively, this gave each state power to legalize and regulate sports betting, and boy did they. Most states have since enacted laws legalizing sports betting (which has lead to more than a handful of scandals since.)

This cultural normalization created a willingness for the Commodity Futures Trading Commission (CFTC) to create structure around “event contracts.” They behavior similarly to futures or options, but the underlying “asset” is an event outcome.

To borrow from The Big Short (one of my favorite movies), here’s Anthony Bourdain to explain:

Let me simplify it. Sports betting is self explanatory, but prediction markets are seen as open option along the risk-spectrum of investing. You could play it safe and buy bonds or blue chip stocks. Maybe you want to venture out on the risk curve and dabble in some small cap stocks. Or you could go full-blown degenerate and dive into meme coins and prediction market contracts.

Look, I’m not trying to poo poo on what people like to do for fun, but I’ve posted countless times about our deteriorating macro economic structure. People (young men in particular) are gambling on anything and everything because they no longer believe the traditional economic frameworks will allow them to get ahead. And you know what… they’re right about that, but gambling on the weather isn’t the answer.

Jenny

P.S. I’ll give credit where credit is due. Prediction market data have been a strong indicator of broader social activity. When a ton of people participate prediction markets can be right where polling is wrong.

Over the next year, Roku predicts that 100% of the streaming audience will see ads. For growth marketers in 2026, CTV will remain an important “safe space” as AI creates widespread disruption in the search and social channels. Plus, easier access to self-serve CTV ad buying tools and targeting options will lead to a surge in locally-targeted streaming campaigns.

Read our guide to find out why growth marketers should make sure CTV is part of their 2026 media mix.

Learn more.

Cristina grew up in São Paulo, built her career inside Brazil’s biggest banks, and quickly saw how broken the system was. In 2013, while pregnant with her first daughter, she co-founded Nubank and ignored everyone who told her the timing was impossible.

Today, Nubank serves over 100 million customers and went public at a $41 billion valuation, becoming the world’s largest digital bank.

Meet Cristina Junqueira, co-founder of Nubank.

How about this week you find one small way to bet on yourself?

Think about a risk in your life you haven’t been willing to take. Something that comes down completely to you.

Take that risk. The biggest wins in my life, whether it be my career moves or starting a family, came from an underlying belief that I would have what it takes when the rubber met the road.

This week’s spotlight goes to one of the most interesting voices in AI, Allie Miller, with a rather fascinating take on the future of AI. We hear about chatbots and browsers, but the future of AI is…voice? Worth a read.

Are you using AI dictation for your work yet?

Want to be featured next?

Make sure to tag @Jenny Stojkovic on your post for a chance to be featured.

I’d love your help spreading the word about The Wednesday Play. Refer other people to the newsletter and get free time with me for a video call.

The Wednesday Play isn’t just a newsletter — it’s a community. I’ll be announcing much more in coming weeks and months! For now, let’s connect across social.

Join 140,000+ followers on LinkedIn!