Westport Journal: Startup Westport – Successful Beyond Expectations

Originally Published at Westportjournal.com on August 8th, 2025

By Gretchen Webster

WESTPORT–With the startup of any new organization, it takes time to attract members, establish the organization’s goals – and even longer to fulfill them. But one Westport organization, Startup Westport, has managed to do all of that and more – in just two years. 

Now numbering 2,100 members, Startup Westport offers several programs for entrepreneurs, a sense of community, and opportunity for its members to excel in technology and other new endeavors, according to several members and leaders of the group.

Forming relationships

“It’s about engagement, support, the formation of relationships – the components to form business relationships,” said Cliff Sirlin, the president of Startup Westport. “It’s a sense of creating an ecosystem to support investors and creators.”

Although there are many members who have been called co-founders, the formation of Startup Westport in 2023 was, by all accounts, a group effort.  The group evolved from the presence of an entrepreneurial spirit in Westport, the introduction of new technology, and the move out of New York by many entrepreneurs and investors during the pandemic, its leaders say.

Ancient history: March 2023

At the group’s first meeting in March 2023, Jay Norris, one of Startup Westport’s co-founders and a speaker at the gathering, took an informal poll of those attending, concluding that about 95 percent were Westport residents, 90 percent had been involved in start-up companies, and 80 percent were investors.

“Ten or twenty years down the road there’s no reason Westport can’t be another Silicon Valley,” Matt Gorin, the keynote speaker and co-founder of Contour Venture Partners, a venture capital firm, said at that meeting.

Since then, the organization has developed many programs including a mentorship program, a Pitch program, special interest groups called SIGs, and a monthly networking get-together.

“I think that we weren’t 100 percent sure what would happen once we got together – it’s an exciting and welcome outcome having this many members in such a short time,” said

 Peter Propp, head of the organization’s new Pitch Program, and vice-president of Startup Westport.

Some of the group’s members have been able to join new companies, acquire investors, or gain “new significant customers because of the group,” Propp said. The group has also attracted members from the academic world including from Yale and Fairfield universities and the University of Bridgeport, among others, he said.

Quickly paid dividends

Member Marc Frankel has had successful outcomes for his business.

 “My membership in Startup Westport has paid dividends very, very quickly,” said Frankel, the CEO of Manifest, a company that secures supply chains. His company was working on a proposal for a U.S. Air Force contract when Startup Westport provided his small company with opportunities for letters of support, investors, and connections with members of the military, Frankel said.

The contract went through after First Selectwoman Jennifer Tooker, also a co-founder of Startup Westport, put him in touch with Gov. Ned Lamont and Congressman Jim Himes, who recommended Frankel’s company to military officials, Frankel said.

“It’s a great place to network,” Frankel said. He uses Startup Westport “for networking and sharing of ideas. People have used it for recruiting. Some have gotten jobs through Startup.” 

Many kinds of support

One of the biggest advantages of belonging to the organization are the many different ways the members offer support to each other, several members said.

The Mentorship program pairs seasoned pros with emerging leaders, according to the Startup Westport newsletter. Although some of the mentees may be young entrepreneurs just starting out, “anybody who wants to start up a business is welcome,” Sirlin said. Over 200 entrepreneurs have already gone through the mentorship program, he said, and some of them are in what he called “the second or third act” of their careers, switching gears, rather than first time jobholders.

Startup Westport is also continuously forming Special Interest Groups (SIGs) which are peer-to-peer interest groups on a range of topics. Some current SIGs include an Artificial Intelligence SIG, which is holding a workshop, “Advanced Robot Solutions,” on Sept. 3, and the Women of Startup Westport SIG, holding a workshop called “Credibility Counts” on Sept. 18. Information for both events and others is available on the Special Interest Groups page of the Startup Westport website. 

Multiple special interest groups

Other SIGs include Cybersecurity, Marketing, and Investor SIGs. 

A new Startup Westport Pitch Competition, with a winning award of $25,000, attracted 70 companies from around the area to apply this year, Sirlin said. Of those, 21 were chosen to receive initial coaching. 

“Four finalists will be chosen in October. “We’re not looking forward to having to make that decision on the final four companies,” said Propp, who is in charge of the competition. “All the companies participating in the competition are great.” The final award ceremony will be held Nov. 20 at the Westport Library.

Another event held by Startup Westport this fall is the organization’s Innovator of the Year Award.  This year’s presentation will be held Oct. 8 at the library with details to be announced soon, according to Kara Curtis, public relations director of the group. The Innovator of the Year Award was first awarded last year to James Pitaro, chairman of ESPN, according to Norris.

Monthly networking events held at local establishments are also a core part of the StartUp Westport program, usually the first week of every month.

Startup Westport is privately funded, according to Sirlin. Sponsors include the Westport Library, the co-working facility Serendipity Labs, The Content Studio of Westport, the Hospital for Special Surgery and the Wiggin and Dana law firm.

For more information on Startup Westport and its events, visit the Startup Westport webpage.

Gretchen Webster

_{^{Gretchen Webster, a Fairfield County journalist for many years, has reported for the daily Greenwich Time and Norwalk Hour, the weekly Westport News, Fairfield Citizen and Weston Forum. She was editor of the Fairfield Minuteman for ten years. She has won numerous journalism awards over the years, and taught journalism at New York University and Southern Connecticut State University.}}