Brown Shoe Company, Founded 1878, Invests in Jack Erwin, Founded 2013

As CEO of a 135-year-old business, Diane Sullivan was looking for new ideas for growth and a fresh take on men's shoes for Brown Shoe Company. She thinks she may have found it in Jack Erwin, an upstart New York City-based online shoe brand that just started selling its footwear last year. Brown Shoe, the public company behind Famous Footwear stores, Shoes.com and brands such as Dr. Scholl's, is leading a $9 million investment in Jack Erwin.