ChoiceStream
Bosco was one of the engineers responsible for building the popular chat tool that hit crazy-popularity in the late '90s and early 2000s. (His screenname was "FastVR6," a nod to his Volkswagon Jetta with a souped-up VR6 engine).
After helping to create the chat client that molded a generation, he decided to take a whack at management. Instead of writing code himself, he wanted to dictate what code other engineers worked on. He eventually joined Advertising.com after AOL bought it in 2004, and became its new COO. That first foray into
Bosco joined ChoiceStream late 2010. At the time, it was a personalization software company that had a great product, but a "poor" business model. As CEO, Bosco was charged with taking ChoiceStream's algorithmic know-how and applying it to advertising.
"It was an incredibly exciting opportunity because it essentially allowed me to bootstrap something - start completely from scratch on a business - but do it within the framework of company already somewhat established," Bosco tells Business Insider. "So it wasn't me with another guy and a couple million dollars of venture capital in a garage, it was me with like 30 people and more money."
Bosco started cherry-picking some of his former Advertising.com coworkers and they had a product ready to launch by 2012, which made it simple for advertisers to automatically bid on digital ads.
By 2013, Bosco completely shut down ChoiceStream's legacy product. The company has grown around 300% year-over-year since then, and he considers ChoiceStream one of the rare stories of a successful pivot, thanks in part to his Advertising.com team.
"Even though we started as a small company - we had zero revenue - we all came from the background of knowing how to manage a company with like $500 million in revenue," he says, "And we've built the same sort of scaling capabilities from day one at ChoiceStream."
The company's new $7.5 million round was led by Fred Alger Management and marks its first fundraise since the pivot.