Robert Reffkin had a hard time fitting in when he was growing up: raised by a single mom in Berkeley California, he was both bi-racial and Jewish, and had to learn to "feel comfortable with being uncomfortable." Even though he was a self-described C student, he was admitted to Columbia and landed a series of prestigious investment banking jobs, but often felt like he was failing. Then in 2012, Robert was tasked with writing a business plan as part of a job interview, but the plan was so intriguing that he was encouraged to launch it as an actual business. So with a partner, Robert launched Compass, a real estate company that focused on building technology to make agents' jobs easier. Less than ten years after launch, Compass is a publicly traded real estate brokerage with 18,000 agents, valued at around $6 billion.