Oscar didn't come from a product roadmap. It came from a Saturday morning, a Strava screenshot, and a question no app could answer.
It started with a habit. After every long run or Ironman session, I would take a screenshot of my Strava activity and paste it into an AI chat to ask for coaching advice. Manual. Repetitive. But it worked.
The problem was the friction. Open Strava. Screenshot. Switch app. Paste. Ask. Wait. By the time the answer came, the window had passed. Training moves fast. Coaching can't lag behind.
So I built a version that did it automatically. Connected directly to Strava, parsed the data, and sent a coaching recap the moment an activity finished. That was v1. It lived on a server, it ran for one user me and it worked exactly as imagined.
The simplest insight: athletes already have Telegram open. Building another app means asking you to install something you'll mute by week three.
Telegram gives Oscar push notifications and voice notes for free. More importantly, it puts coaching where the conversation already happens in your pocket, not behind a login screen.
Graphs don't make you faster. Decisions do. Oscar gives you the one paragraph that matters, not a screen full of metrics to interpret yourself.
Coaching that arrives 48 hours after a session is history, not guidance. Oscar fires the moment Strava closes the activity.
One subscription. One channel. No tiers, no add-ons, no upsells. Oscar should feel like a coach, not a SaaS product.
Every feature in Oscar exists because I needed it first. There's no product team guessing at athlete problems from a conference room.
Designer by training. Athlete by obsession. I compete in long-distance endurance Ironman and ultra trail and have been chasing the intersection of technology and performance for years.
Oscar is the tool I wanted to exist. The fact that other athletes want it too is what turned a personal project into a product.
Questions, feedback, or just want to talk training? skyftlab@gmail.com