Skateboarding & Business Lessons

By Trevor Fenner | Updated 2026 I didn’t move to Bali because it was comfortable. I moved because my life in Los Angeles had become something I didn’t recognize anymore. A marriage that had turned toxic, a routine that felt more like a rut than a life, and a persistent sense that I was capable […]

By Trevor Fenner | Updated 2026 Not everything I build is about revenue. That might sound strange coming from someone who runs a dropshipping education platform, an ecommerce store, and a portfolio of niche content sites. Most of what I do is deliberately built around generating income and the specific kind of freedom that income

By Trevor Fenner | Updated 2026 Skateboarding has a culture that most people on the outside don’t fully understand. From the outside it looks like a hobby. Kids at a park doing tricks, maybe filming clips, maybe getting hurt. What it actually is, when you’re inside it, is one of the most demanding and character-forming

By Trevor Fenner | Updated 2026 There is a specific kind of mental fatigue that comes from running multiple online businesses. It’s not the same as physical tiredness. You can sleep eight hours and wake up still carrying it. It’s the accumulated weight of open loops: campaigns that need monitoring, supplier relationships that need attention,

By Trevor Fenner | Updated 2026 Nobody feels motivated every time they skate. That might sound obvious but it took me a long time to really internalize what it meant. I grew up thinking that the days I skated well were the days I showed up wanting to skate, and the days I skated poorly

By Trevor Fenner | Updated 2026 I’ve been skating since I was a kid in Seattle and building businesses since I was in my twenties in Los Angeles. For most of that time I thought of them as completely separate pursuits: one was how I stayed sane and connected to something physical and creative, the

By Trevor Fenner | Updated 2026 I learned how to fall before I learned how to land anything. That’s not a metaphor. In skateboarding, learning how to fall safely is genuinely one of the first things you develop as a skill. How to bail off a board without breaking your wrists. How to roll out