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The shift happened fast. Social media became the way people share content clips, and vertical video changed consumption patterns; the social platforms moved distribution from controlled channels to everywhere simultaneously.

Jack's observation: "There's been more change in the last seven to eight years than maybe the 40 years before with distribution."

Every league is responding to this change. The NBA is doing things with creators. The NFL is working with YouTube, and F1 started working with creators, for example, Amelia Dimoldenberg’s Passenger Princess series.

The question isn't “should we work with creators” - it's how to do it without confusing it for becoming a media company yourself.

"I think every big company is trying to evolve, and it's a seismic shift," Jack says. Sports are one of the only things with a truly shared culture. One of the last parts of monoculture in a rapidly changing media world.

That's why creator partnerships matter. They're how marketing-led businesses (leagues, teams, properties) reach audiences where they already are without abandoning their actual business model.

The creators are delivering the news

Jack invested in Jomboy Media in late 2019 or early 2020. Jimmy O'Brien had built something rare—a baseball breakdown channel that made the sport relevant to digital and younger audiences in a way no one else did.

"I give the whole team there a lot of credit. Jimmy was posting to Twitter every day. Then he got to a thousand Twitter followers, and now his company does hundreds of millions of views every week."

*Much like myself, this merely started as an interest in writing on LinkedIn a few years ago because the traditional paths were closed to me. So I created my own.

The MLB partnership was mutually beneficial in a specific way. MLB is a big league. They don't need any individual creator, but if they were going to work with one, this was the guy. Jimmy makes baseball relevant for a YouTube audience, a younger audience, in a way that nobody else does.

For Jomboy, the company was already profitable and growing. "The great thing about being growing and profitable, you don't need any investment." So neither side needed the deal, which is exactly why it worked.

Jack's take: "I don't think either side needed the deal. I think it was the right time because MLB, like every other big company on earth, is looking at its creator strategy and saying, what are we doing? How are we reaching audiences where they are?"

The partnership allows for expanded content creation where Jomboy presents at events like the All-Star Game. This was a first-of-its-kind deal where a league took a stake in a creator company.

That signals something changed about how leagues view creator relationships and growing their fan base.

The biggest thing is community and engaged audience a depth of connection that is tough to replicate for any right-holder. Unless you’ve built the sport for the last 100 years. You need the kind of stories where fans say, “My dad and family were fans of this team, by association, so am I”

The type of connection you get from watching old Murray Walker commentary clips.

Jack breaks this down clearly: "I think that ultimately the leagues and rights holders, their business relies on new fans and deeper engagement from the current fans. The biggest thing that Jomboy has built is really a community that has trust."

There are a lot of views on the internet. You can find any random YouTube video or account with 7 million followers; heck, there are fireplace videos that have 100 million views.

What matters is the depth of impact and community strength.

Evidence of that depth shows up in specific ways.

When an epic moment happens in Major League Baseball, people tag Jomboy, saying, "Where's the breakdown?" That organic demand - fans asking for the creator's take when something significant happens—signals real value.

If we take a traditional media look, it’s like when people ask Dave Chappelle on a particular topic because his voice and words land with impact. “Did Chappelle say something about this?”

Jack experienced this firsthand in 2021. "I remember one time, Jimmy, Jake, and I went to a game in Milwaukee. And there was a line from like around first base, where our seats were, out of the stadium to take a picture with this guy and meet this guy. And when I saw that, I was truly amazed."

That was 2021. The audience has grown significantly since then, but the pattern was already clear: depth of connection with reach.

The comments on Jomboy videos show people talking about how he brings excitement to MLB and explains the game in a fun and relatable way. They’re not scrolling on the phone while watching the video; the kind of consumption doesn’t apply here.

Leagues need this more than ever: new fans and deeper engagement with current fans. Getting the foundations and fundamentals right.

To my point at the top, creators’ partnerships working shouldn’t mean "we should become creators and be a media company ourselves."

F1 wouldn’t build Pirelli tyres in-house; that’s why they have a partnership with Pirelli.

They see creator partnerships working and think different things entirely.

Jack invested in Jomboy Media, knowing it's a media-led business. Content IS the product. Revenue comes from content monetization—advertising, partnerships tied to viewership, the content itself generating income.

MLB is a marketing-led business. Content markets the product. Revenue comes from live games, broadcast rights, sponsorships, and tickets. Content serves to make those more valuable.

The partnership works because each side stays in its lane. Jomboy creates content that makes baseball more relevant to digital audiences. MLB gets access to that audience and relevance. But MLB isn't trying to become Jomboy. They're partnering with him to strengthen their actual business.

This is the critical distinction right-holders can underestimate. Working with creators doesn't mean becoming creators and owning every distribution channel. It means using creator reach and trust to strengthen your marketing-led business model.

At a certain point, you can’t expect every single function be in-house. Yes, there is more control, but also extra maintenance.

"Everyone needs a media strategy now," Jack says. "The question is—how do you not fall too in love with being a media company when that's not your business model?"

Creator partnerships are a media strategy. Right-holders who confuse these end up spending resources trying to replicate what creators do naturally instead of partnering with creators who already have it.

Jack has a framework for this from an investment perspective. When evaluating businesses, he looks for organic demand as the number one leading indicator.

For creator partnerships, the same framework applies. You're evaluating whether a creator has organic demand you can partner with.

The tests:

Purchase-driven intent appears early. "You see purchase-driven intent quickly," Jack explains. "If you don't see it early or early-middle, don't expect it to come easily." For creators, this means merch sales, event attendance, and willingness to pay for access. Jomboy sells merch. Comments form their own community. That's purchase intent beyond just watching free content; people vote with their wallets.

Average user session time matters. "When people just spend all their time there - that's depth of passion you can grow." Creators whose audience watches entire breakdowns have deeper engagement. That engagement transfers when you partner with them. Look at the Amelia Dimoldenberg F1 “Passenger Series” she created.

Willingness to wait signals real demand. Jack talks about "how long are people willing to wait for something? People are willing to wait in line for something for two hours. What does that mean? Demand exceeds supply." The Milwaukee stadium line for Jimmy O'Brien demonstrated this physically. Digital version is fans waiting for breakdowns to drop after big moments. I know my British counterparts and colleagues love a queue.

Community self-organisation. When fans create their own content about the creator, organise their own discussions, build communities around the content - that's depth you can't manufacture. Jomboy's comments section has become its own community discussing baseball beyond just reacting to videos.

These signals separate creators with real community depth from those with large but shallow followings.

Jack's observation about media strategy applies to creator partnerships: "It's very hard, not impossible, but very hard to layer a media strategy or layer a voice after the fact. How is your voice built native to your company from day one?"

Native creator integration means a partnership built into the overall strategy. The "pay creator to post about us" is rudimentary. A structural partnership asks, "How does this creator relationship strengthen our core business?"

MLB-Jomboy works because it's native. Jomboy was already the biggest baseball content creator, and MLB evaluating creator strategy naturally leads to "work with the guy who's already making baseball relevant to the audience we need to reach." Integration makes sense for both sides.

Compare this to the transactional approach: property sees creator with a big following, pays for one-off activation, creator posts, nothing changes. That's layered activity.

Native integration asks:

→ How does this creator help us reach new fans?
→ How does their content deepen engagement with current fans?
→ How does a partnership structure allow both sides to grow?

The answer determines deal structure:

But it's always tied to how the creator strengthens your actual business model—live events, sponsorships, broadcast value.

How do you partner with them to make your business more valuable?

You're identifying creators who already have community depth in your space and figuring out a partnership structure that makes your core business more valuable.

Jack's investment thesis applies: he's betting on differentiated consumer experiences where consumer preferences show social status and identity. Being a Jomboy fan is a form of social identity. Being a baseball fan who watches Jomboy is a more specific identity than just "baseball fan."

Right-holders have a similar dynamic. Being a supporter of a specific team, attending races, and wearing merchandise. That's an experience business; creator partnerships should strengthen those experiences and make them more valuable.

The evaluation framework is straightforward:

Does this creator have community depth?

Does their audience overlap with fans you need to reach?

Can you structure a partnership that strengthens your core business?

Is this native integration or transactional activity?

These questions separate partnerships that build value from expensive experiments that don't connect to how you actually make money.