Small business owners collaborating with mentors at a hands-on AI workshop
ArticleNovember 22, 2025

Main Street Meets AI: Inside OpenAI’s Small Business Jam

CN
@Zakariae BEN ALLALCreated on Sat Nov 22 2025

Why 1,000 Small Businesses Spent a Day Building with AI

Running a small business is a familiar rhythm: serving customers, managing schedules, monitoring cash flow, and finding time for marketing after hours. With time at a premium and technical expertise often limited, the growing capabilities of AI offer small businesses hope for increased efficiency, improved operations, and innovative customer engagement.

This is the idea behind OpenAI’s Small Business AI Jam, a nationwide workshop held on November 20. Over 1,000 entrepreneurs gathered in five cities—San Francisco, New York City, Houston, Detroit, and Miami—to craft practical AI tools they could implement immediately. Sponsored by OpenAI Academy in collaboration with DoorDash, SCORE, and local business organizations, this event provided participants with the mentorship needed to create tailored workflows that directly benefit their businesses. Each attendee walked away with one or more ready-to-use AI solutions.

What Made This Event Unique

  • Inclusive for Non-Experts: No prior coding or machine learning experience was necessary. The focus was on straightforward, repeatable workflows that small teams can easily manage.
  • Results-Oriented: Every participant left with a practical tool addressing real tasks like marketing copy, customer communications, scheduling, and inventory management.
  • Local Support: Collaborations with local chambers of commerce and community groups ensured that the day was rooted in local business needs.
  • Ongoing Resources: An online resource hub prepared business owners ahead of the event, and an online Skill Lab on December 4 provided additional learning opportunities and continuing support.

Significance for Main Street

Small businesses are vital to local economies but often lack the time and resources to explore new technologies. A recent OpenAI survey revealed that many small business owners expect employees to be proficient with AI, as these skills can lead to significant efficiency improvements.

This trend aligns with recent data: a survey highlighted by Axios shows that 36% of small businesses are already utilizing generative AI, with an additional 21% planning to adopt it within the next year—often leveraging free or low-cost options. There is a palpable interest in AI; however, gaps remain in time, training, and practical applications.

Who Attended?

The Jam attracted a diverse cross-section of businesses: from accountants and law firms to restaurants and food trucks, neighborhood retailers, creative studios, and service providers. The goal was not to create fancy prototypes, but to develop practical workflows that lessen repetitive tasks and enable owners to concentrate on revenue-generating activities.

Five Hubs, Local Partnerships

To ensure the event catered to local needs, OpenAI Academy collaborated with various local organizations in each hub:

  • Detroit: Detroit Means Business, New Economy Initiative, Michigan Chamber of Commerce
  • Houston: Texas Association of Business, Houston Area Urban League – Entrepreneurship Center
  • Miami: The Idea Center and AI Center at Miami Dade College, Florida SBDC at FIU, Greater Miami Chamber of Commerce
  • New York City: Five Chamber Alliance
  • San Francisco: Renaissance Entrepreneurship Center (REN Center), SF Chamber of Commerce

Partners like DoorDash and SCORE facilitated mentorship and practical guidance based on years of supporting local merchants.

Tools Participants Built

Here are some examples of the practical tools created during the event:

  • Marketing Copilots: Draft weekly emails, social media posts, and menu updates in the brand’s voice, incorporating seasonal promotions.
  • Customer Messaging Assistants: Convert common inquiries into consistent responses, allowing for seamless handoffs to human staff when needed.
  • Operations Helpers: Automatically generate prep lists, shift summaries, and task boards based on calendar entries or daily checklists.
  • Inventory and Scheduling Tools: Summarize sales notes or past appointments and recommend adjustments in staffing or purchasing.

OpenAI Academy’s resource hub provides ongoing support with step-by-step guidance, prompt packs, and instructional videos, allowing teams to continue refining their AI assistants after the Jam.

A Quick Tour of the Jam Playbook

For those who couldn’t attend, here’s a summary of how mentors guided teams to quickly create usable tools:

  1. Clarify the Job-to-be-Done: Identify a time-consuming task (e.g., appointment follow-ups or daily specials). Collect a few real examples of past communications to reference.

  2. Define Quality and Constraints: Draft a brief outlining the target audience, tone, essential details, and what the tool should avoid doing. Establish success criteria.

  3. Build the First Version Using ChatGPT: Input the brief and examples into ChatGPT to create a reusable template. Test with real scenarios and identify areas for improvement.

  4. Add Structure: Request outputs in a specific format, including a checklist for compliance and key details.

  5. Customize: Save the best versions as custom GPTs or prompts. Integrate data sources like calendars or spreadsheets if applicable.

  6. Pilot the Tool: Use the assistant daily for one week, track time savings and any necessary adjustments.

Practical Applications Across Industries

Different industries created tools that showcase the versatility of AI:

  • Restaurants and Food Trucks: Develop an assistant to create daily specials with related captions and prep lists.
  • Retailers: Build a product spotlight generator that formats inventory notes into engaging social media content.
  • Home Services: Automate job proposals and follow-up emails based on standardized templates.
  • Professional Services: Generate client summaries with actionable items and discussion points for initial meetings.
  • Creative Industries: Create iterations of mood board captions, client updates, and a revision log.

These outputs reflected the practical, repeatable workflows participants built during the Jam.

Insights on AI Adoption

OpenAI has now reached over 1 million business customers, with companies developing applications directly on the platform. The surge in enterprise AI adoption coincides with increasing interest from small business owners seeking immediate benefits in areas like marketing and customer service. Yet, there’s a clear need for hands-on training and support—a gap the Jam effectively addresses.

Beyond One Day: A Continued Commitment to Small Businesses

The Small Business AI Jam is part of a broader series of events designed to empower diverse groups, including past initiatives with nonprofits and scientists. This model promotes collaboration, skill development, and feedback to shape future resources and products.

Furthermore, OpenAI is committed to extending AI opportunities beyond large corporations, launching new community-focused initiatives that include funding for nonprofits and programs to cultivate AI-ready talent in small businesses.

OpenAI has also endorsed bipartisan legislation aimed at providing clearer guidance and strengthening training resources for small business AI adoption, reinforcing the Jam’s emphasis on practical skill development.

Partner Ecosystem Tailored for Main Street

With deep experience in small business support, DoorDash and SCORE brought invaluable insights to the Jam. DoorDash’s programs leverage AI to assist local sellers, enhancing menu presentation and campaign effectiveness. During the event, mentors helped participants pinpoint day-to-day challenges and translate them into practical automations.

Local partnerships ensured that the content resonated with each community’s unique characteristics, from Detroit’s manufacturing focus to Miami’s vibrant hospitality sector.

Responsible Adoption: Essential Guardrails for Small Teams

Responsible AI adoption is crucial, particularly for small teams handling both marketing and sensitive personal information. Resources from the Academy emphasize practical and straightforward practices:

  • Clearly communicate when customers interact with AI-generated messages versus human responses.
  • Safeguard sensitive data within appropriately designed systems; avoid relaying confidential information unless fully compliant with protocols.
  • Utilize a short approval checklist for outgoing content—especially for pricing and promotions.
  • Start with low-risk applications (such as drafting or summarizing) and gradually explore more impactful automations.

The Jam’s structured approach fosters these habits, empowering owners to continuously refine their AI applications post-event.

What If You Missed the In-Person Jam?

OpenAI Academy is offering a free, virtual Skill Lab for the Small Business Jam on December 4. This hour-long session will cover the fundamentals of prompting, help you build your first workflow, and provide you with a usable tool by the end.

How to Maximize Value in 30 Days

Use this four-week plan to transition from a workshop experience to sustaining long-term gains:

Week 1: Launch Your Assistant
Choose a process with clear return on investment, such as weekly emails or social media posts. Transition it to your new assistant and track time savings.

Week 2: Structure Your Approach
Save a best-practice prompt and convert it into a custom GPT or use it as a guiding template. Develop a simple content calendar or job management system using your assistant’s outputs.

Week 3: Gradually Expand
Add an integration that minimizes manual data handling, like a spreadsheet for offers or a shared folder for approved images. Implement a quality assurance checklist across outputs.

Week 4: Evaluate and Adjust
Assess the outcomes against your initial metrics: time saved, conversions, average order values, etc. If improvements are evident, consider adding another use case; if not, refine your focus on the highest-impact tasks.

Frequently Asked Questions

Q1) Who is the Small Business AI Jam for?
Targeted at owner-operated businesses with 1-100 employees—including restaurants, retailers, service providers, and online shops—no technical background is needed.

Q2) Do I need to know how to code?
No. The Jam is tailored for non-technical teams, using step-by-step guidance, personalized examples, and straightforward prompts to build usable tools.

Q3) What will I take away?
At least one ready-to-use workflow or assistant (like a marketing copilot or customer messaging assistant), along with resources for ongoing improvement.

Q4) Is there an option to participate virtually?
Yes! The Small Business Jam: Online Skill Lab is scheduled for December 4, featuring live Q&A and a beginner-friendly format.

Q5) How does this relate to broader OpenAI initiatives?
The Jam extends the reach of previous Jams and contributes to OpenAI’s community funding and business platform, promoting accessible and practical AI education.

Final Thoughts

AI is no longer a futuristic concept for small businesses; it’s a practical tool that can streamline tasks, enhance customer communication, and expand online visibility. The Small Business AI Jam illustrates how focused, hands-on learning can yield immediate benefits—one day, one challenge, one effective solution ready for implementation. With access to mentors, local partnerships, and an ever-expanding reservoir of resources, Main Street is equipped to harness the potential of AI and continue thriving.

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