Few early-stage investors can rival Boldstart Ventures founder Ed Sim’s record at picking founders before they even have a business plan. It’s earned him a spot on the Midas Seed List for a third year.took the mic at a Hawaii tech meetup to share a warning: The nascent boom in investment in artificial intelligence would start a new heightened game of cat and mouse between companies with valuable information and hackers looking to access it.
Sim, who started writing early checks in 2010 long before the boom in seed funds, specialized in backing enterprise and infrastructure startups from New York when “Silicon Alley” was more of a digital desert. He left the city in 2022 for Miami, where he’s now become one of the few investors to have stuck around after the pandemic-era Techxodus ended. “By the time I left, New York had become a thing with every single West Coast VC moving in,” Sim said.
In the very small world of late 1990s New York venture capital, Sim was introduced to Salomon Smith Barney vice chairman Bob Lessin, an angel investor. When Sim asked Lessin for a reference for his Harvard Business School application, the Wall Street heavyweight instead made him an offer. “Bob said, ‘I’m going to start a new venture fund, Dawntreader, and I want you to run it for me,’” Sim said. “If we fail you can always reapply to Harvard.
Those bets started paying off: GoToMeeting was later acquired by Citrix for $225 million, LivePerson IPOed in 2000 and Answers.com listed on the Nasdaq in 2005. Dawntreader’s second fund launched in 2000 and was more than 10 times the size of its original fund. The hangover from the 2008 financial crisis meant that Boldstart would begin with just a $1 million fund—but it now manages over $500 million of assets. Sim credits seeing his own parents’ determination, and spending a college summer selling Cutco knives door to door, for the drive that helped him grind through the lean years.
While many seed investors prefer not to be on their portfolio companies’ boards, Sim said he sees his board member role for BigId and Snyk as a consigliere to the founders and a go-between for larger investors who can temper premature scaling efforts or spiraling costs.