Welcome to Digital Main Street

The New Forum for Main Street’s Future

Our Partners

Programs & Resources Just For You

Tailored solutions that help small businesses grow, scale, and succeed through personalized advisory, education, and community connection.

Industry Vertical Forums

Connect with others in your community, fostering collaboration, referrals, and shared local initiatives that strengthen neighborhood economies

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Closeup group Asia businesspeople talk ESG strategies risk management workshop, SDGs report, global warming, green finance and investment and net zero waste in boardroom training building.

Resource Sharing

Share both physical and knowledge-based resources across industries and local economies, unlocking new efficiencies and collaborative growth opportunities

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Educational Workshops

Access educational content, peer insights, and guidance from industry experts, helping you build skills, stay competitive, and grow with confidence

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AI Advisory

Receive expert advice to harness artificial intelligence to streamline operations, enhance decision-making, and unlock new value

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Business people signing a contract in the office.

Business Exit Support

Tap into expert advisory, consulting, and valuation services referral network designed to support strategic growth, succession planning, and business transitions

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Industry & Community Based Network

Gain access to industry and community-based networking opportunities, connecting with peerswho share local roots and business goals

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Global Reach. Local Impact.

MainSquare connects small business owners to a global network of knowledge, tools, and shared resources—empowering them to scale smarter, navigate challenges, and learn from peers across industries and borders.

At the same time, we reward owners who provide meaningful insights and expert knowledge in support of other owners within their own industry.

By bridging global insight with hometown action, MainSquare helps small businesses thrive where it matters most.

Two Paths, One Platform — join as a Main Street Member to share, or as a Main Street Investor to discover

Find Your Community

Main Street Owner

$25

per month

More info

Who You Are: You’re a small business owner, operator, or family entrepreneur who’s built something real — and you’re looking to make it stronger, smarter, and more valuable. Share your experience, connect with peers, and gain visibility within the MainSquare community—while earning rewards for contributing knowledge that helps strengthen Main Street businesses everywhere.

Access to industry vertical forums

Recognition as a contributor

Resource library with guides and templates

Peer-to-Peer messaging with other owners

Access to AI advisory and valuation services

young man entrepreneur handshake with female financial adviser

Main Street Partner

$75

per month

More info

Who You Are: You’re a consultant, advisor, or support professional who helps Main Street businesses thrive. You might design websites, build systems, manage marketing, implement AI tools, or provide accounting, legal, or valuation support. Join the MainSquare Partner Network — where professionals connect directly with Main Street business owners ready to grow, modernize, or exit. Showcase your expertise, build trust, and access a pipeline of verified businesses looking for professional support.

Custom business profile with logo, bio, case studies, and service listings

“Verified MainSquare Partner” badge

Ability to tag industries and specialties

Visibility on the Service Marketplace for business owners looking for professional help

Ability to bid or offer proposals directly through the platform

Portrait of confident businessman in glasses and with arms crossed leaning on white wall in office

Main Street Investor

$120

per month

More info

Who You Are: You’re an investor, buyer, or acquisition-minded professional seeking real opportunities on Main Street. You value data-driven insights, verified businesses, and the human stories behind each deal. Exclusive access to a proprietary database of small businesses, industry insights, and owner-shared knowledge—empowering investors to identify opportunities, assess value, and connect directly with Main Street entrepreneurs.

Full access to the proprietary Small Business Deal Database

Searchable library of owner-contributed insights

Advanced filtering by industry, geography, and size

Quarterly investor briefings and data trend reports

Investor-only community forum for networking

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“MainSquare helped us bring AI into our daily operations—something I never thought a small business like mine could afford or understand.”

— Linda M., Owner, Landscaping Business

“With MainSquare’s AI Advisory team, we automated our scheduling and customer follow-ups. It’s like having another employee, but smarter and faster.”

— David R., Founder, Cleaning Services Business

“They guided me through every step of selling my business—valuation, buyer introductions, negotiations—everything. I didn’t just sell, I transitioned the right way.”

— Karen P., Former Bakery & Café Owner

“The valuation report MainSquare provided opened my eyes. I finally understood what my business was truly worth and how to make it more valuable before selling.”

— Miguel T., Owner, Auto Repair Shop

“MainSquare helped us bring AI into our daily operations—something I never thought a small business like mine could afford or understand.”

— Linda M., Owner, Landscaping Business

“With MainSquare’s AI Advisory team, we automated our scheduling and customer follow-ups. It’s like having another employee, but smarter and faster.”

— David R., Founder, Cleaning Services Business

“They guided me through every step of selling my business—valuation, buyer introductions, negotiations—everything. I didn’t just sell, I transitioned the right way.”

— Karen P., Former Bakery & Café Owner

“The valuation report MainSquare provided opened my eyes. I finally understood what my business was truly worth and how to make it more valuable before selling.”

— Miguel T., Owner, Auto Repair Shop

“MainSquare helped us bring AI into our daily operations—something I never thought a small business like mine could afford or understand.”

— Linda M., Owner, Landscaping Business

“With MainSquare’s AI Advisory team, we automated our scheduling and customer follow-ups. It’s like having another employee, but smarter and faster.”

— David R., Founder, Cleaning Services Business

“They guided me through every step of selling my business—valuation, buyer introductions, negotiations—everything. I didn’t just sell, I transitioned the right way.”

— Karen P., Former Bakery & Café Owner

“The valuation report MainSquare provided opened my eyes. I finally understood what my business was truly worth and how to make it more valuable before selling.”

— Miguel T., Owner, Auto Repair Shop

Connect With Our Team

Reach out to MainSquare in Chicago for small business and investment inquiries.

Empower Your Business

Unlock your business potential by connecting with investors ready to support your entrepreneurial journey.

Connection Clarifications

Who MainSquare for?

MainSquare is designed for two core user groups: Main Street Members (small business owners who want to share knowledge, access tools, and build value) and Main Street Investors (buyers, advisors, and partners seeking vetted small business opportunities).

How is MainSquare different from other small business platforms?

Unlike traditional networking sites or brokerage listings, MainSquare integrates AI-driven insights, verified business data, and community-driven knowledge sharing—creating a transparent, trusted ecosystem for small business growth and transition.

How can MainSquare help me grow my business?

Through educational workshops, AI advisory support, and peer networking, MainSquare helps you modernize your operations, strengthen your valuation, and gain exposure to investors and partners.

What are Verified Leads, and how do I become one?

Verified Leads are businesses that have implemented technology and AI tools to improve transparency and efficiency. To become verified, you’ll complete our readiness assessment and meet specific operational and data criteria—signaling to investors that your business is ready for transition or partnership.

Is there a free trial or demo?

MainSquare offers a limited-access preview of community forums and select tools so new users can explore before subscribing.