Top 15 Serial Entrepreneurs In The World T op 15 Serial Entrepreneurs in the World. Click to skip ahead and jump to the Top 5 Serial Entrepreneurs in the World. Serial entrepreneurs start new companies, make them successful, and sell them to move on to their next startup. Serial entrepreneurship is on the rise in the U.S. Success stories of figures like Twitter founder Jack Dorsey, Square founder Jim McKelvey, Facebook’s Mark Zuckerberg, Gumroad’s Sahil Lavingia, 23andMe’s Anne Wojcicki and several others are fueling inspiration across the country among young people to launch startups. Data from PitchBook and the National Venture Capital Association suggest that venture capitalists invested a whopping $156.2 billion into domestic startups in 2020 alone.