Get Woke Go Broke is an expression typically used to express the sentiment that companies who embrace political correctness or cave to demands of social justice activists will suffer financially as a result.
On April 17th, 2018, the Milo Yiannopoulos-run news site Dangerous published an article about sci-fi author John Ringo, which quoted Ringo using the phrase "get woke, go broke" in the context of organizations that cave "to SJW pressure."
On June 17th, 2018, Urban Dictionary user Skua September submitted an entry for the phrase, stating "when organizations 'get woke' to politically correct actions, those same actions usually result in a massive loss of income" (shown below).
On August 16th, YouTuber TheQuartering uploaded a video featuring the phrase in the title, which discussed a controversy surrounding the game Battlefield V (shown below, left). On August 20th, YouTuber The Thinkery uploaded a video titled "Get Woke Go Broke" about the controversy (shown below, right).
On September 12th, YouTuber Timcast uploaded a video with the description "Get woke go broke" about reduced college enrollment at Evergreen College (shown below, left). On October 3rd, YouTuber Assertonsin [Asmongold Stream Reactions] uploaded footage of World of Warcraft streamer Asmongold commenting on a controversy with Blizzard referencing the phrase (shown below, right).