There is something very easy about Tyler. He is laid back, cool, funny, loves football, and somehow talks about building and selling one of Canada’s fastest growing consumer brands like it was all fairly normal.

It wasn’t.

Inkbox started because Tyler wanted a tattoo, but not forever. That curiosity eventually took him to the Darien jungle in Panama, where he found the fruit and molecule that became the foundation of the product. That willingness to go deep on a problem matters.

So does scrappiness. They started with $15,000, used Kickstarter to validate demand, and literally handed people $20 notes to help game the algorithm and get momentum on the platform. It worked. Then timing kicked in.

Tattoos were becoming more mainstream. Instagram was taking off. Digital ads were still relatively cheap. Venture capital gave them access to people and benchmarks they did not yet have themselves. One conversion rate improvement helped take revenue from around $8 million to $20 million.

There is a useful reminder in that. Great businesses need execution, but timing can massively amplify good execution. By the time BIC came knocking, Inkbox had around $40 million in revenue, 170 people, serious IP, and 44% brand awareness among under 40s in the US. Unreal.

They were actually raising a Series B at the time. That made the decision interesting. Keep going, raise more money, and roll the dice for another few years… or take the certainty of a major exit while consumer spending was starting to soften and digital acquisition was getting harder. They sold for around $90 million. Claps very loudly. Well played lads.

I loved Tyler’s description of the deal in three moments. Telling the team. Watching the TV coverage with his brother, parents and partners, while his mum cried downstairs. Then sitting in an Uber when the money hit his account and basically thinking, “sick.” Very Tyler.

The corporate chapter afterwards was harder. Less control. Slower decisions. More politics. Eventually both brothers left before the full earn out period was complete.

And that is where his next chapter gets interesting. Tyler took time off, travelled, built a music studio, learned a language, and started investing partly to keep what he calls his “business muscle” working.

Then he and his brother started again. But this time the game is different. Olauto is not about chasing another giant exit. It is about building something they like, in a category they enjoy, with people they want to work with, while keeping the business cash positive and manageable. He does not need to prove he can do it again.

What I like about Tyler is that the second act feels liberated rather than restless. He is still building, still investing, still staying sharp, but without letting the business consume everything around it. His line near the end sums it up perfectly.

The business serves his life. He does not serve the business.

That is a pretty good definition of winning the second time around.