Charles "Kip" Moore (1943-2015) / photo courtesy of the Maine Venture Fund

Charles “Kip” Moore (1943-2015) / photo courtesy of the Maine Venture Fund 2008 File Photo/The Associated Press

Maine’s startup community lost an important member this week.

Charles “Kip” Moore was a technology pioneer (he was on the student team at Dartmouth that developed the BASIC computer language) and one of the first venture capitalists in Portland to invest in early-stage Maine companies. He was a mentor to entrepreneurs and served on the boards of several local companies.

Moore died Jan. 26, 2015. He was 71.

Moore, who founded his VC 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 VC firm with offices in Portland and Cambridge. “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.”

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 when he met Moore, who had offered to mentor some of the Top Gun students, in 2009. Cianchette’s startup, Liquid Wireless, was a pioneer in mobile advertising that he would eventually sell to Publishers Clearing House in December 2011, but at the time he met Moore he was a young entrepreneur with “nothing going for me,” he said.

“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…” Cianchette said Thursday. “It made me feel important, and that what I was doing was important. It’s really hard as an entrepreneur. I had no employees, basically no money. I had nothing going for me.

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

Don Gooding, director of MCED and the Top Gun program, remembers an early conversation between Moore and Cianchette, who he called the “poster child for Top Gun.” Cianchette came in saying his first priority was raising the venture capital he needed to build his business, remembers Gooding. Moore, however, offered a different strategy.

Cianchette doesn’t remember the interaction, so I’ll let Gooding, who blogged about Moore’s recounting of the memory in December 2012, take it from here:

“Kip gently suggested that maybe talking to customers ought to come first, to make sure there was demand. 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 in January of 2012 – even though his ‘lead generation from cell phone users’ business could probably have raised angel investment.”

“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.”

Moore, who was never an investor in Liquid Wireless, was invaluable to Cianchette when Publishers Clearing House, the direct marketing company famous for its sweepstakes offers, came knocking with an offer to buy the company.

“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 for me through the whole process. … He gave me a lot of confidence, he really helped me think things through properly.”

Liquid Wireless was doing well and 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.”

Cianchette, Agnew and Gooding and others that knew Moore, say he 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 warchest to fill his shoes,” Cianchette said.

Moore was born Oct. 23, 1943, in Plainfield, New Jersey, and grew up in upstate New York, according to his obituary published in the Portland Press Herald. While at Dartmouth, Moore was part of the student team that helped develop the BASIC computer language and build the Dartmouth Time Sharing System. He received a PhD 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 we all know 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 and focused 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 technology companies.

Throughout the years he invested in 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 that asked tough questions and remembered the answers. His advice was invaluable to me as a CEO — he made us better.”

Moore did not seek the limelight, according to those who knew him. (That’s likely to blame for my not being able to find any mention of him in the Portland Press Herald’s archives.)

“Kip was unique,” John Burns, manager of the Maine Venture Fund, told me. “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.”

Burns himself thought of Moore as a mentor. Before going to work at the Maine Venture Fund 15 years ago (it was known as the Small Enterprise Growth Fund at that point), Burns was a portfolio manager at Unum. His experience had been in trading large-cap stocks and bonds. He had no experience in venture capital and investing in early-stage companies.

“It was on-the-job training and it was from people like Kip that I really learned the trade of public equity investing,” Burns said.

Burns remembers Moore as a selfless investor and mentor.

“My sense was he didn’t do it because he needed the return,” Burns said. “I think he did it because he loved working with entrepreneurs and big dreams and big visions. He enjoyed being a part of that.”

In what is perhaps the greatest tribute to Kip Moore’s legacy, Cianchette said it was his influence that led him to want to give back to Maine’s startup community. Despite being busy 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 that 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.”