Maine’s startup community is mourning the loss of a man described as “the dean of venture capital in Maine.”

Charles “Kip” Moore, 71, who died Monday, was a technology pioneer, starting when he was part of the student team at Dartmouth College that developed the BASIC computer language. But he was known locally for his commitment to early-stage Maine companies as one of the first venture capitalists in Portland, as a mentor to entrepreneurs and as a director on the boards of several local companies.

Moore, who founded his venture capital firm Little Diamond Island Enterprises in 1993, was “the dean of venture capital in Maine,” said Tim Agnew, a principal at Masthead Venture Partners, a venture capital firm with offices in Portland and Cambridge, Massachusetts. “He was the one everybody wanted to work with. They wanted his money not just because of the money, but because he brought so much value (to a company).”

Jason Cianchette, one of Portland’s most successful entrepreneurs, benefited greatly from Moore’s mentorship.

Cianchette was a member of the Maine Center for Entrepreneurial Development’s inaugural Top Gun class in 2009 when he met Moore, who had offered to mentor some of the Top Gun students. Cianchette’s startup, Liquid Wireless, was a pioneer in mobile advertising that was sold to Publishers Clearing House in December 2011. But at the time he met Moore, Cianchette said, he was a young entrepreneur with “nothing going for me.”

“I was a 32-year-old at that point, and to go up into his nice office and for him to give me all that time, … it made me feel important, and that what I was doing was important,” Cianchette said Thursday. “It’s really hard as an entrepreneur. I had no employees, basically no money.

“He always encouraged me to think bigger with the company, especially back then.”

Don Gooding, director of the Maine Center for Entrepreneurial Development and the Top Gun program, remembers an early conversation between Moore and Cianchette, whom he called the “poster child for Top Gun.” Cianchette came to the program saying his first priority was to raise venture capital that he needed to build his business, recalls Gooding.

“Kip gently suggested that maybe talking to customers ought to come first, to make sure there was demand,” Gooding recounted. “A few weeks later when they met again, Jason said something like, ‘I don’t need funding – I talked to some customers – they want to buy the product now!’ That was a better path for Jason – he owned the whole company when he sold it – even though his ‘lead generation from cellphone users’ business could probably have raised angel investment.”

But Moore encouraged Cianchette to boot-strap the operation and retain total ownership.

“He was by no means trying to come in and scoop up great ideas for himself,” Gooding said Thursday. “He was trying to help entrepreneurs do the right thing.”

It was sage advice. Several years later, Liquid Wireless was doing well and drew the attention of Publishers Clearing House, the direct marketing company famous for its sweepstakes offers, which made an offer to buy Liquid Wireless. The company was “quite profitable” at that point, so Cianchette admits he was thinking of declining the offer. Moore made him reconsider.

“I was happy and doing well, but he had seen companies like mine before and said it’s not a guaranteed thing. ‘You don’t own a hardware store and the future is not certain and markets change, technologies change,’ ” Cianchette remembers Moore telling him. “We were doing well then, but it wasn’t clear how long that would last and he was adamant at that point about the need to get acquired or to get capital because at that point the race was heating up in mobile advertising.”

Moore, who was never an investor in Liquid Wireless, was invaluable to Cianchette for his mentorship.

“This was a new experience for me. I didn’t really know what to do,” Cianchette said. “I reached out to him and he was my No. 1 resource through the whole process. … He gave me a lot of confidence, he really helped me think things through properly.”

Cianchette, Agnew and Gooding say Moore was a great asset to Portland’s startup community and will be sorely missed.

“It is a huge void now without him because there’s really not a comparable person with his experience or war chest to fill his shoes,” Cianchette said.


Born in Plainfield, New Jersey, Moore grew up in upstate New York, according to his obituary in the Portland Press Herald. While at Dartmouth, Moore was part of the student team that helped develop the BASIC computer language and built the Dartmouth Time Sharing System.

He received a Ph.D in computer and communication sciences from the University of Michigan and went on to teach computer science at Cornell University. He joined Automatic Data Processing Inc. – the payroll company now known as ADP – in 1975. In 1982, he moved to New York City and became a general partner at the venture capital firm Welsh, Carson, Anderson and Stowe, focusing on investments in technology and information processing companies.

After a successful career in venture capital, Moore moved to Maine in 1992 and founded Little Diamond Island Enterprises the next year. It was one of Maine’s earliest venture capital firms and made early-stage investments in Maine technology companies such as The VIA Group, IntelliCare Inc., Harbor Technologies and Tilson Technology.

“Kip helped provide growth capital in our company when we needed it most. We were big enough to be taking on huge projects, but not big enough to attract Boston-area investment,” said Josh Broder, Tilson’s CEO. “More importantly than the capital, Kip was a member of the board who asked tough questions and remembered the answers. His advice was invaluable to me as a CEO – he made us better.”


“Kip was unique,” said John Burns, manager of the Maine Venture Fund, who had been mentored by Moore. “He didn’t have a whole lot of ego. He was pretty quiet, pretty mild and always had a steady disposition. He wasn’t one to panic.”

In what is perhaps the greatest tribute to Moore’s legacy, Cianchette said it was his influence that led him to give back to Maine’s startup community. Despite launching a new business and raising three small children, Cianchette is making the time to act as a mentor for a new crop of entrepreneurs who are part of the new Top Gun class, which is the largest ever.

“I’m hoping in some small way to replicate what he gave to me,” Cianchette said. “It’s personally been logistically challenging, but it was such a benefit that he gave me, I’m hoping I can help in whatever way I can.”