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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.
Every week, 1 Million Cups gives entrepreneurs a platform to present their business to a supportive community for ideas and connections to grow it. It's not a pitch; it's a chance to learn and collaborate.
REGISTRATION
The Founders Roundtable Series continues in October. This eight-session monthly gathering brings 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 discussing how to find a problem worth solving. We’ll unpack the mindset shifts, questions, challenges, and opportunities that come with identifying a product or service that people will actually pay for, drawing on the experiences and perspectives of founders in the room.
Hour 2 will feature Kim Walpole, a serial entrepreneur and product leader who has spent her career building mission-driven companies from the ground up. She previously founded Trials.ai, where she raised venture capital, built and scaled the company, and ultimately led it through an acquisition by ZS. She also mentors founders and emerging tech companies, helping them think through product, growth, raising capital - and most importantly, what it takes to build something people will actually use.
Today, Kim is co-founder and CEO of FiveLoaves.ai, a Charleston-based startup using responsible AI to help churches and everyday leaders understand Scripture within its historical and cultural context, lead better conversations, and care for people well.
Kim is a visionary founder who tends to see what could be before it exists, and she is most energized by building things that have the potential to leave the world better than she found it.
REGISTER
A weekend hackathon where every team builds a project with an AI agent as a teammate.
The agent is a persistent synthetic teammate that can retain project context and contribute throughout the weekend; humans remain responsible for direction and final decisions.
This is a team sport.
Participants are required to be part of a team. You are welcome to come with a team fully or partially formed. You are also very welcome to show up with an idea you want to build a team around or to find an idea/team that you like. There will be plenty of time Friday night to match people up.
Embrace the non-human.
Teams must included at least two humans and one or more non-humans. We are taking a very wide view on what counts as a non-human. This could include a long running Claude session, a ChatGPT-powered agent, an OpenClaw instance, a robot of your own design, or something else entirely.
Go for the gold.
This is a competition. Our judges will decide a winner on Sunday night. The winning team gets $1,000 and the second place team gets $500. Teams will be judged on the commerical and/or social value of their idea, to what extent they have realized that idea, and how thorougly they engaged with their non-human collaborator(s).
Not all gold glitters.
Prizes are great, but there is more value to find at HarborHack. Networking with judges and mentors might be the connection that unlocks that next step in your career. Finding now collaborators may help you take that side project to the next level. Inspiration strikes more often when you are in a room full of the inspiring.
Submission Requirements
To be eligible for judging, every team must complete a Devpost submission before the deadline.
Your submission should include:
A clear name for your project.
In 2–5 paragraphs, describe:
Provide a public repository whenever possible.
If your repository cannot be public (for licensing or other reasons), explain why and provide judges with a way to review the code.
Because this year's theme is Agent In The Loop, every submission should include a brief reflection describing your collaboration with one or more non-humans.
Examples include:
We're judging the collaboration—not just the software.
Every team will present live.
Your demo should clearly communicate:
Projects will be evaluated on:
Longleaf Angels
An early-stage investing community rooted in the Southeast (and Charleston)
Presenter: TBD
Date: Wednesday, November 4, 2026
Time: 12:00 Noon to 1:00 PM
Registration: Click here to register
Join this presentation with Longleaf Angels, a local member-led community of angel investors, to learn how they are bringing together emerging and experienced investors to back promising early-stage companies, build diversified portfolios, and support founders with more than capital.
A hands-on workshop for figuring out where AI belongs in your business and where it doesn’t.
AI CAN DO IT. SHOULD IT?
AI can do more than most business owners realize. The harder part is knowing when it is actually worth using.
Bring a real business problem you’re trying to improve. You’ll examine what’s happening, question assumptions, and explore where AI could genuinely improve the work before spending more time or money on a solution.
You’ll see AI working inside a real business workflow, then use AI to challenge your thinking about your own business—while deciding what still needs human judgment.
Leave with a concrete next step and a way to think through future business decisions, too.
A hands-on workshop for founders, business owners, and people who play a key role in how a business runs.
November 6, 2026
11:00 AM arrival | 11:15 AM program begins | 3:30 PM event ends
The AKU Venue Event Center | Moncks Corner, SC
Free to attend | Lunch and refreshments included | Limited seating
No advanced AI experience required. Bring a laptop if you have one and make sure you can access the AI tool you already use. If you don’t have a laptop or AI account, you can still participate.
Founders. Builders. Operators. Investors. Ecosystem champions.
Join us this November 10th 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.
RSVP
See the Lowcountry's top entrepreneurs pitch live for a share of up to $2 million in potential investment.
Thursday, November 12
The Founders Roundtable Series continues in November. This eight-session monthly gathering brings 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 discussing how to find a problem worth solving. We’ll unpack the mindset shifts, questions, challenges, and opportunities that come with identifying a product or service that people will actually pay for, drawing on the experiences and perspectives of founders in the room.
Hour 2 will feature JT White.
J.T. White is an accomplished product leader and entrepreneur with over 15 years of experience in developing digital products. He has worked on a diverse range of projects-from online rap battle websites and TV Everywhere applications for Showtime and NBC, to advanced AI-driven inventory management and allocation tools. He is now the Co-Founder of an AI-assisted video studio. In 2025, he published Build for Better: How to build successful digital products and companies.
ABOUT CHUCKTOWN STARTUPS
CONTACTS
toby@chucktownstartups.comCharleston, SC 29403
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