We all know that during the pandemic, Westport’s population expanded as an influx of folks relocated to our area. One of the most interesting outcomes of that demographic shift is that we became a hub for tech professionals, with many relocating to the area in search of a vibrant community, access to talent, and a strategic base for remote work, further fueling the region's growth as a key player in the innovation and startup sectors. In response, StartUp Westport was founded by Cliff Sirlin, Peter Propp, Dan Bikel, Jay Norris, Sam Hendel, First Selectwoman Jennifer Tooker, Chief Foti Koskinas, Matt Gorin and Stefano Pacifico with the mission to foster a dynamic, innovative ecosystem where entrepreneurs, investors, and professionals can collaborate, network, and grow. It aimed to leverage Westport's unique blend of affluent professionals and proximity to major tech and finance hubs to create a space where the startup community could thrive and, as a result, is increasingly being referred to a “Silicon Sound.”
In just the last year, the number of startups in the area has increased by 40 percent, and there are now more than 1,800 members of StartUp Westport, which include not only tech startups but investors, service providers, and corporate partners who see the potential for innovation in the region. Kara Curtis recently joined as the Head of Marketing and Communications at StartUp Westport. Her strategic leadership has played a key role in raising the organization’s visibility, driven targeted marketing campaigns that have enhanced brand awareness, engaged the community, and attracted high-quality members, partners, and investors to support the region's growing innovation ecosystem. With this huge membership base and a strong leadership team in place, StartUp Westport has targeted three key areas of focus as the culture in town continues to embrace tech entrepreneurs and venture capital:
Tentpole Events
StartUp Westport has hosted major events, including the Innovator of the Year award featuring Jimmy Pitaro, which attracted over 400 attendees, and the Young Innovators Spotlight, which brought together Staples alumni to discuss how this community created a foundation for them to develop groundbreaking innovations. The events have also served as key networking platforms, where entrepreneurs meet investors, mentors, and potential collaborators. They also highlight the growing influence of Westport as a tech and startup destination, with more companies choosing to relocate to the area because of the vibrant ecosystem.
The Mentorship Program
Recognizing the value of experience and guidance, StartUp Westport launched its Mentorship Program to connect budding entrepreneurs with established industry experts. Led by Noah and Susan Fenn, the program has quickly grown to one of the largest mentorship programs in the state with over 260 participants. This initiative provides one-on-one mentorship, and small group mentorship circles, offering advice on topics such as building a business plan, fundraising, marketing, and legal considerations. Mentees consistently report that the program accelerates their growth by providing them with targeted advice, invaluable connections, and confidence to navigate the complex startup world. One example is Bari Schrager, who left a successful media career at Condé Nast to launch GOMME, an AI-powered retail media network transforming in-store marketing for the liquor industry. StartUp Westport paired her with Kal Amin, who joined 1848 Ventures as Managing Partner, eager to build AI-driven ventures focused on the SMB market—while continuing his commitment to mentoring the next generation of entrepreneurs. Their shared background in media made for an ideal match. With Kal’s guidance, Bari refined her strategy and secured Kindred Spirits & Wine—a local Westport business—as a real-world testing ground for GOMME’s beta launch. The impact was immediate: sales lifted for all beta advertisers, customer engagement increased by 34 percent, and major liquor brands took notice—leading to $1.5M in proposal requests. “Kal’s mentorship, along with the support from local partners like Kindred Spirits & Wine, has been crucial in our journey from concept to beta, and now to real-world demand,” says Bari. "As we move into the next stage of growth, I’m incredibly grateful for this community—it’s been a great resource and a wonderful way to connect with fellow entrepreneurs." Now, as Bari prepares for the next stage of growth, Kal continues to advise her. “Working with Bari has been incredibly rewarding. The power of collaboration makes our mentorship ecosystem truly special,” agrees Kal.
Special Interest Groups
StartUp Westport recently introduced Special Interest Groups (SIGs) led by Kal Amin to address the growing demand for sector-specific focus. These groups include topics like cybersecurity, artificial intelligence, fundraising and investment, and women in technology and innovation, offering a space for entrepreneurs to discuss challenges, share resources, and collaborate on sector-specific opportunities. The SIGs have become an essential part of StartUp Westport's programming, providing specialized support for members who want to dive deeper into their fields.
And even with all this, StartUp Westport is still innovating. In the coming months, they will launch the "Founder Stories" series, where members will share the unique journeys that led them to start their businesses. These stories will be featured in newsletters and on the StartUp Westport website, giving exposure to local founders and providing inspiration for others in the community. In addition, the "Visionary’s Podcast," hosted by Jay Norris, will showcase interviews with influential thought leaders, local innovators, and successful entrepreneurs. The podcast will cover a wide range of topics, from emerging trends in technology to personal stories of overcoming challenges in business, providing valuable insights to the entire community. Plus, an updated membership directory is on the way to improve networking opportunities. There’s never been a better time to be part of a startup in Westport. To learn more, visit startupwestport.org
"The power of collaboration makes our mentorship ecosystem truly special.”