Jason Stein — $25,000

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Jason Stein is one of the lucky ground floor opportunists who got in when Instagram was still 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, and this work lined his pockets with some serious coin.

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, for he’s having a blast with this medium.