🔴 How "the worst business owner of all time" built two successful personal brands

Jack Appleby has one of the most popular social media strategy newsletters in the industry. He also has an entirely separate second personal brand as a washed-up basketball player.

He claims he’s "the worst business owner of all time,” which clearly isn’t true. If anything, his work just shows how far passion-driven creative work can take a content business before adding infrastructure to scale.

In this episode:

— Natalia Pérez-González, Assistant Editor

🎧 If you prefer a podcast platform other than YouTube, we’re on Apple, Spotify, and all the rest.

Do you want to advertise an open role in Creator Spotlight? Reply to this email.

By Natalia Pérez-González

Jack Appleby is terrible at running a business. That’s what he told us, at least; by every visible metric, he’s built two successful creator businesses.

A social media veteran, Jack entered the industry in 2011, back when Facebook was the primary social media platform and the term “social strategy” barely existed. His first agency job was on the graveyard shift, spending all night managing a team replying to Facebook comments for an Electronic Arts video game launch.

There was no playbook. Everybody was still figuring our the rules and Jack thrived on his ability to improvise.

Since then, he's worked on social strategy for Microsoft Surface, Twitch, and Verizon. He's also built two personal brands with substantive followings and six-figure audiences. And he’ll tell you, plainly, that he’s the “worst business owner of all time.”

He's ghosted brands mid-campaign. He once let a dream opportunity — to pitch basketball star Luca Dončić's team, to manage his personal brand — slip away because he was too depressed to respond to the email thread, let alone build a deck.

And yet:

He may be flawed as an operator, but as a creator, he’s a consistent success. Creative, narrative work seems to come easy to him; it’s scaffolding the business around that work where he’s now realized he needs help.

Jack’s popular newsletter, Future Social, was born by accident.

As part of their creator program, Morning Brew recruited Jack to write a social media newsletter in 2022, after seeing the success of his marketing takes on Twitter. Jack told us he would’ve never taken the initiative to launch the newsletter on his own; he’s too risk-averse.

A year later, Morning Brew shut the program down with little notice — but they did right by him, giving him the rights to his newsletter and all 35,000 subscribers. He migrated the list to beehiiv and kept publishing.

Since then, he’s doubled the audience through organic growth alone. Despite his claims of having no business skills, he’s also built a full-time-equivalent living rooted in his newsletter:

With one personal brand in motion, back in 2023, Jack, quickly beginning to feel burnt out on his weekly marketing essays, started posting basketball videos on his personal Instagram. He had no strategy at the time, no growth goals. The hook was simple: “34-year-old washed-up ex–college player trying to get back in the game”

The third video hit a million views on a 7k-follower account.

In a basketball internet dominated by bravado and highlight reels, Jack positioned himself as the opposite: self-deprecating, team-first, humble. Turns out there was plenty of audience demand for this against-the-grain style.

A pattern emerged. Each new series he launched reliably added around 10k followers each.

These series have so far included rec league MVP runs, a Warriors-hosted 3x3 tournament, and founding a professional team. The Warriors series averaged 300k views per video, even though he had only 40k followers. Linear growth, driven by serialized storytelling.

Now, his work is all about systematizing instinct. He recently signed with Wishly Group for management; deals are closing at rates he never would've asked for himself. He's relaunching his course, figuring out how to crack marketing video, and leaning further into vulnerability as a brand strategy. His next sponsored campaign — with a financial institution — is built around the same blunt pitch: I'm the worst businessman alive.

The creative expertise was always there. He’s reaching towards new heights by bringing in experts to cover his business blinds and build new infrastructure around that core skill.

Connect with Jack on LinkedIn.
Subscribe to Future Social.

Jack's How to Hoop Forever growth followed a repeatable pattern: announce a multi-part series with a compelling premise, document the journey across 4 to 10 videos, and deliver narrative payoff at the end. Each major series drove roughly 10k new followers. Here's how he structures it.

Every series begins with a premise people want to see resolved:

The hook is attention-grabbing and piques people's curiosity about the outcome; every premise is just implausible enough.

Jack's Warriors tournament series, for example, averaged 300k views per video on a 40k follower account. The stakes were clear, the journey was documented, and the audience stuck around to see how it ended.

Jack thinks in narrative arcs. He's scripting during games — noticing a play he made, identifying the visual hook, then building the story around it. By the time he's on the subway home, he's already written the voiceover in his head.

It’s a muscle he’s built over time; as he spent more time editing his basketball content, he built an innate understanding of what types of shots he’d need to capture the next time he filmed.

Each of his individual videos serves his larger series. A clip of him scoring zero points in a 120-point game, for example, then becomes content about finding joy in team basketball.

But only if it makes sense for your brand.

Jack's highest-view-count month on TikTok came after beef with two other basketball creators. He framed his argument around team basketball versus individual play (framing himself as the humble, level-headed team player and them as the hot-headed individualists), tagged the players, and his followers showed up to defend that philosophy.

Their audiences continued the argument in the comment sections, and soon enough, Jack and one of the creators were DMing each other, hyping each other up. The debate was real, but all parties were knowingly fanning the flames.

The videos earned Jack millions of views and nearly $10k in TikTok Creator Rewards. The controversy worked because it fit into his narrative and reinforced what his audience already believed; they showed up to defend team-first basketball.

Jack asks himself a core question for every piece of content: Why should someone root for me? Views without loyalty don't compound. An audience that believes in your mission will watch every video in a series, share your content, and buy whatever you're selling.

This is what separates sustainable creator businesses from viral moments. Jack's basketball content is wholesome because that's who he is — a guy who wants aging rec league players to believe they can still enjoy the game. A guy who wants high school kids to understand that playing the right way can earn scholarships even without elite athleticism.

It’s easier to create serialized narrative content when it’s authentic to your beliefs and passions.