Homeboy x tendlyn.

The first video Tom Oswald ever posted from Homeboy was about nobody showing up.

He’d just opened a popup in a small art shop in Hahndorf, a tourist German town outside Adelaide. There was an unused espresso machine. He started making coffee. Day one, the only customer was a friend. So he made a video: opened a cafe and nobody came.

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News publications picked it up. Headlines about a boy who opened a cafe and failed his dream. People felt bad for him. But Oswald wasn’t sad. He’d expected a quiet start. He thought it was funny. And he kept posting.

That was two years ago. Homeboy is now in the middle of Adelaide, near the universities, serving a younger crowd. The popup that was supposed to be short-term ran for a year. The videos that started as documentation became the engine.

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Document Everything

Oswald had worked in cafes before, in high school and the year after. He’d also run a clothing brand, which is where the interest in branding came from. He taught himself graphic design on an iPad. When it came time to build Homeboy’s identity, he did 90% of it himself.

But the thing that actually built the audience wasn’t the logo. It was the content.

People liked watching someone gradually improve. The fails and the successes. The quiet days and the busy ones. Instagram and TikTok for the fast stuff, YouTube for the slower day-to-day. The approach hasn’t changed since that first video: just document what’s happening.

“As long as I’m doing that, that’s honesty,” Oswald says.

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Your Homeboy’s Spot

The name came from his dad. They’d been brainstorming for ages, throwing out ideas every day. Homeboy was the first one everyone agreed on.

“It’s like going to a friend’s house instead of going to a restaurant,” Oswald says. “It’s your homeboy’s spot.”

The vibe matches the name. Takeaway focused. Grab and go. Staff who clearly like being there. Quality control that doesn’t let anything leave the counter unless it’s right.

And then there’s the cinnamon scrolls.

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Mom’s Scrolls

Oswald’s mom makes the cinnamon scrolls. That’s not branding. That’s just how it works.

But Oswald sees opportunity everywhere. He loves starting businesses. When he saw the play on words, the homemade angle, the story, he pitched his mom on building something around it. She’d never had a business before. She said yes.

They’re now considering spinning the scrolls into their own shop, separate from Homeboy. For now, they’re still part of the menu, alongside the made-to-order focaccias and the coffee.

“It’s exciting for her as well,” Oswald says. “And it’s just fun.”

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What’s Next

Homeboy started as a popup with an unused espresso machine and a joke about failure. Two years later, it’s a city cafe with a loyal following, a content strategy that actually works, and cinnamon scrolls with a potential spinoff.

The thing that got it here wasn’t a marketing plan. It was honesty. Documenting the quiet days. Posting the failures. Letting people watch the whole thing unfold.

That first video still holds up. Opened a cafe and nobody came. A million people watched. And then they kept watching.