Tech bros move fast and break things, and none wields the hammer as aggressively as Elon Musk, the Tesla CEO who now owns Twitter. In just a few days of ownership, Musk has laid off half the staff, alienated advertisers that provide most of the company’s revenue and proposed several changes that might drive users away. Many regular tweeters fear Musk will let anybody post anything, turning the platform into a gusher of nasty propaganda.

The Twitterverse may be in shock, but this is nothing new for Musk. Since starting his first company in 1995, Musk has built a remarkable entrepreneurial career on bold moves that sometimes seem reckless and unfiltered opinions he rarely apologizes for, no matter who he offends.

A review of Musk’s many ruckuses reveals he has become brasher as his successes have multiplied. Unlike most CEOs, Musk has no fear of controversy, and may actually relish it. He pushes boundaries and usually gets away with it. When venturing beyond his areas of expertise, Musk’s views can seem naïve, but they reflect boundless confidence in his ability to solve any problem—which he’s now applying to Twitter. Here’s are some of Musk’s memorable dust-ups over the years:

2009

Co-founder spat. Martin Eberhard, one of five Tesla co-founders, sues Musk over his ouster two years earlier in a battle for control of the company. Musk and Eberhard settle on confidential terms.

2010

“Trophy wife.” Musk’s first wife, Justine Musk, publishes an article asserting that Musk tried to mold her into a “trophy wife,” along with other personal insights into Musk’s formation. Musk has been married three times to two women and has dated celebrities such as Amber Heard and Grimes. He has at least nine children and jokes he is “doing my best to help the underpopulation crisis.”

Going after critics. Musk fights back after the New York Times trashes Tesla’s first sedan, the Model S, saying the car conked out on a highway. Musk personally rebuts the review in a Tesla blog post, citing data logs from the car that supposedly disprove the Times’s assertions. The Times rebuts the rebuttal, leaving the truth somewhat cloudy—but proving Musk’s tenacity in the face of criticism.