Founders. Builders. Operators. Investors. Ecosystem champions.
Join us this September at Over the Horizon Brewing for an evening of real conversations and real connections inside Charleston’s startup community.
Come early, grab a drink, and meet someone who could change the trajectory of your business.
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REGISTRATION
This September, we’re launching the Founders Roundtable Series, an eight-session monthly gathering bringing Charleston founders and entrepreneurial leaders together to connect, share ideas, learn from one another, and help shape the future of technology and entrepreneurship in our community.
Hour 1 will be an interactive founder roundtable exploring the leap from entrepreneurial idea to founding a company. We’ll unpack the mindset shifts, questions, challenges, and opportunities that come with turning an idea into a real business, drawing on the experiences and perspectives of founders in the room.
Hour 2 will feature Barry Stamos, a three-time exited founder and CEO of Supernova, a collective of 250+ exited founders who have built and sold their own companies and now invest in, advise, and serve as operating partners to the next generation of builders.
Barry’s featured presentation, “Do or Die: What Founders Need to Know,” will offer a candid look at what it really takes to build a company, navigate the inevitable challenges, and make the decisions that can determine whether a startup survives or succeeds.
Barry has built companies for 25+ years. His first, INBOX Marketing, became Responsys, went public, and sold to Oracle for $1.6 billion. His second, Videoo, failed after four years chasing product-market fit. As a founding partner at Acxiom, he built a business unit from zero to $318 million that exited to IPG for $2.3 billion. He is also co-founder and Chief Heart Officer of 1heart.com, a startup studio and human accelerator with 1,000+ alumni worldwide.
As a founding advisor, Barry has helped build category leaders. He backed Colossal Biosciences, the first de-extinction company, which raised a total of $615 million to become a decacorn in under four years and established the Colossal Foundation with $100 million to support habitat restoration and genetic rescue. He also backed Tuft & Needle as it bootstrapped to $250 million in ARR before merging with Serta Simmons. He also backed and served as Head of Investor Relations at Arora Project, an equity crowdfunding agency that raised $115 million-plus for startups before its exit to Republic. Prior to that, Barry was the Entrepreneur in Residence at 500 Global, one of the most active VCs globally, where he supported startups chosen for their flagship accelerator program out of San Francisco.
Barry lives in Mount Pleasant, SC with his wife Christine and two teenage boys, Beau and Nico.
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Five Founders. Five Minutes. Real Feedback.
Whether you're validating your very first idea or growing an established business, Chucktown Startups 5x5 LIVE is your opportunity to share what you're building and receive valuable feedback from fellow entrepreneurs and supporters.
Each event features five founders, each with five minutes to present their business, product, service, or idea. NO PITCH DECKS. Following every presentation, the audience will have the opportunity to ask up to three questions or offer supportive comments and constructive feedback to help each founder move forward.
Event Schedule
5:30 PM | Networking
Meet fellow entrepreneurs, innovators, investors, mentors, and startup supporters before the presentations begin.
6:00 PM | 5x5 LIVE Pitches
Five founders take the stage - NO PITCH DECKS, followed by audience Q&A and feedback after each presentation.
Who Should Pitch?
Entrepreneurs at every stage are welcome, including:
No matter where you are in your entrepreneurial journey, we'd love to hear your story.
How Do I Sign Up to Pitch?
Only five founder presentation slots are available for each event. Founders interested in pitching must sign up in advance to be considered for a presentation slot.
Who Can Attend This Event?
All local founders and community supporters are invited to attend.
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Spindle Venture Studio
Transforming exceptional ideas into successful enterprises
Presenter: Matthew Gough, Managing Partner
Date: Wednesday, October 7, 2026
Time: 12:00 Noon to 1:00 PM
Registration: Click here to register
Join Managing Partner, Matthew Gough, to learn about Charleston's very own venture studio, Spindle, and how it can be a game-changer for the founders in the Chucktown Startups community.
Exceptional startups and entrepreneurs have the power to reshape the world. Spindle expedites innovation, transforming promising ideas into successful enterprises. As a dedicated team, Spindle ideates, validates, and launches businesses, providing resources through every life cycle including access to funding and leadership. Their goal is to streamline early-stage development, reduce risks, and drive successful outcomes - a more efficient and scalable approach compared to the traditional start-up model.
ABOUT CHUCKTOWN STARTUPS
CONTACTS
toby@chucktownstartups.comCharleston, SC 29403
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