He kicked off with OWS, yeah. He was pretty good on-the-ground reporting, responsible for a couple of the horror stories coming out of the actual encampment in NYC. When the 2017 Milo/Berkely/Proud Boys fights kicked off, he was covering them, but got too famous. Antifa and leftover OWS people recognized him and started targeting him at events.
The last live event he personally covered, I think was a campus speech by the feminist who did The Red Pill movie a few years back. He went with his brother as cameraman, got surrounded by SJW protesters and backed up against a wall. They threatened and yelled at him until security could extract them. After that he started making more YouTube videos from his desk just to have content, then changed his format to match what the algorithm would promote, then changed again to weather the Adpocalypse, until he turned into the article-reading clickbait you see today. Happened in the space of about 2 years, it was sad to see.
He did start his own news company,
SCNR/Subverse News. It's a couple of people who alternate between on-the-ground summary reporting, and more in-depth long form story summaries. It's decent journalism, but pretty dry, and his reporters have the same problem Tim himself does: they can't show their face at radical leftist events because they'll be recognized and attacked.