These days, top college athletes pull in NIL earnings that rival pros, and players with large followings are venerated as cultural icons. But back in 2017, having an online presence could tank your career. Just ask Donald De La Haye — better known as Deestroying — who lost his scholarship and spot as UCF’s kicker because his YouTube channel got too popular.

The channel started as a creative outlet between classes and football. “I didn’t see anything wrong with what I was doing,” he says. “I was a marketing student applying what I learned.” The NCAA didn’t see it that way.

After months of back-and-forth, De La Haye was given an ultimatum: stay at UCF or keep making videos. “YouTube wasn’t as big back then,” he says. “Nobody thought you could make a career out of it. I just had a hunch things would work out.”

And they did. Dee now boasts more than 6.4 million YouTube subscribers, 3 million Instagram followers, and a career path no one had really carved out before him. With that audience came real income, mainly through YouTube advertising — which he calls “very lucrative,” — plus brand deals and even a stint with the San Antonio Brahmas in the UFL.

Dee didn’t grow up around wealth; he had to learn how to manage it on the fly. “A lot of people come up, make a bunch, spend a bunch, and before they know it, there’s nothing left,” he says. “I wanted to make sure I had something for the future and start building real generational wealth.”

That mindset led to his biggest business move yet: a $1 million investment in Fat Tuesday’s, the frozen specialty drink chain known for its to-go daiquiris. He discovered the brand while filming at the Super Bowl in New Orleans, connected with CEO Alex Monahan, and told him to get in touch if he ever needed investors.

Two weeks later, the phone rang. Today, Dee owns the Tempe and Westgate Fat Tuesday’s locations in Arizona — and he’s far from done. “I’m grateful for the two stores I have, but I want to own more,” he says. “And I want to use my platform to bring more people through the door and grow those checks.”

Athletes at every level should be leveraging their online presence into tangible business opportunities—through promotional deals, sure, but more importantly by owning equity.

Still, not everyone gets to go to the Super Bowl and sit down with CEOs. Our mission at A&A is to put companies directly in front of professional athletes looking for investment and advisory roles, removing the friction from partnerships like this one.

I asked Dee…

LZ: “Do you see this as a model other athlete creators should follow — using the money they make to break into other types of businesses?”

This was his response…

Deestroying: “100%. I’ve been trying to talk to a few friends and a couple of other people I know about the opportunities coming up for Fat Tuesday in other cities.

I’m just trying to find prominent figures in those places who can pop out and follow the same blueprint I’m using. I think it’s a great lane for people to get into.

As I said, content doesn’t last forever. Clout doesn’t last forever. So if you can figure out something that puts food on the table and helps you make money outside of your posts online, that’s a really good idea.

More influencers and athletes should look into it. They already do merch and all that, but actually getting involved in a business and finding ways to amplify it is a no-brainer, especially if you have equity and real stakes in it.”

What’s up squad? Noah here, barging in because you’re missing out on incredible opportunities 🫵🏻

We’re excited to share that we’ve built a basic analytics dashboard for companies using our platform, so they can see who is viewing their information and how. Companies will receive email notifications when select parties view their deck.

We are enabling some of our readers to take their companies to the next level, leveraging our community and audience. Pretty cool stuff. Selectively refer a founder who you think will break out.

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Will the inclusion of flag football in the 2028 Olympics provide a springboard for popularity and opportunities? I don’t think it’s a simple answer.

Flag football has a few things working in its favor that make it a unique market opportunity. It’s already growing. The NFL reports that around 2.4 million kids under 17 in the United States now play organized flag football, and more than 20 million people play globally across more than 100 countries.

The game is more accessible than tackle. Flag can be played almost anywhere, equipment costs are lower, and both men and women can participate without major structural changes. The sport is also easier to scale internationally because its rules and physical demands are simpler. It won’t compete with tackle football in national popularity, TV rights, or merchandising, and it doesn’t need to.

The more interesting opportunity is the ecosystem around the sport. If flag football keeps growing and gets even a modest boost from the Olympics, the surrounding infrastructure should become the focus. There’s room for league-organization tools, ranking and analytics systems, coaching platforms, scheduling software, training apps and content, and even skill-specific development tools tailored to flag. Is the sport big enough to monetize?

Only time will tell, but I would bet on people who figure out those layers to capture the most value. What part of this ecosystem gets built first, and who is best positioned to build it?

From Deestroying’s rise as the world’s most famous kicker to Gotham FC winning a championship in the other kind of football (sorry, Europe), this week’s edition required a lot of legwork. And I know exactly what you’re thinking…

You right now: “Gee, I wish there were a company that provided high-tech tools for muscle recovery and performance enhancement, such as percussion massage guns, vibrating fitness rollers, and pneumatic compression systems!”

From the Hypervolt to the Vyper to the Normatec, Hyperice has a gadget for all those highly specific needs. I tested the Normatec leg sleeves myself (photo above), and my legs haven’t felt that relaxed since before I ran my first mile in 6th grade. Truly transformative stuff.

And I’m not alone. Patrick Mahomes, Naomi Osaka, and Chris Paul are just a few names on Hyperice’s investor all-star roster. So if your legs are tired after reading about all that kicking today, click here to learn more about Hyperice.