Jason Stein — $25,000

Jason Stein is one of the ground floor opportunists who got in when Instagram was in its infancy. He had a vision and drive to turn his posts into collaborative entrepreneurial relationships with big-name brands and social media influencers.

His own company, Laundry Service, is still going strong, with over 30 employees and counting. Taking social media promotion to the next level is what he does best, and he’s not likely to retire soon as his posts continue to bring in big bucks.