One of the most exciting initiatives for solo entrepreneurs came from DoorDash and OpenAI. On November 20 they hosted a Small Business AI Jam, gathering more than 1,000 small business owners across San Francisco, Detroit, Houston, Miami and New York for hands-on workshops. Each participant worked with mentors to build an AI assistant tailored to their needs — for example, a restaurant owner could create a tool to write menu descriptions, track inventory, or plan dinner rush staffing. By the end of the day, attendees left with at least one working AI solution they could deploy immediately.
Why does this matter? OpenAI and DoorDash believe AI will unlock major productivity gains for small businesses; the event was designed to ensure family restaurants and local shops aren’t left behind. If you didn’t attend the jam, you can still replicate the experience. Here’s how:
- Define your pain point. Choose one repetitive task that eats up your time, like drafting product descriptions or forecasting weekly inventory.
- Choose a general-purpose AI assistant. Tools such as ChatGPT, Claude or Perplexity offer free plans that can generate text, summarize documents and answer questions. Use them to create a prototype script or workflow.
- Iterate with prompts. Refine your assistant by asking it to use your brand voice, follow your policies or adapt the tone for different channels. Within an afternoon you can have a customized AI helper delivering real value.
- Watch for future jams. DoorDash and OpenAI plan additional events, so follow their announcements and sign up when a session is nearby.
Insurance for the AI Era
As more solopreneurs integrate AI into their workflows, new risks emerge. What happens if a customer receives incorrect advice generated by a chatbot? Who covers losses if an AI-powered marketing tool inadvertently creates discriminatory copy? Recognizing these gaps, insurance provider Counterpart announced on November 26 that it is expanding its Affirmative Artificial Intelligence Coverage and launching a Technology Errors & Omissions (E&O) agreement. The coverage specifically protects small businesses against AI-related claims such as inaccurate reports, biased outputs or faulty automation.
Most existing professional liability policies are “silent” on AI, which means claims arising from automated decision-making may be denied. Counterpart’s new endorsements provide clarity. Mike Muglia, the firm’s professional-liability lead, notes that as more businesses rely on AI to process information and deliver services, these endorsements give brokers practical solutions for claims stemming from bad outputs, decision errors or machine-generated bias. If you’re experimenting with AI, it’s worth speaking with your insurance provider about gaps in your existing coverage and whether a product like Counterpart’s fits your needs.
Tools You Can Start Using Today
Constant Contact’s Marketing AI
Marketing platform Constant Contact recently added AI capabilities that are especially useful during peak sales periods. Dave Charest, the company’s Director of Small Business Success, explained that users can enter the date of a sale or event, and the AI will automatically generate draft email, social media and SMS messages across channels. You still review and edit the content, but starting with an AI-generated plan saves considerable time. This feature can be a lifeline for solo entrepreneurs juggling marketing with daily operations. To try it, log into your Constant Contact dashboard and look for the AI-powered campaign planner.
Google Ads’ AI Max for Higher Conversions
Google has quietly rolled out an experiment called AI Max, which uses artificial intelligence to optimize search and shopping ads. According to Salesforce data cited by the U.S. Chamber of Commerce’s small business advice portal, AI Max is already driving 26 % more conversions for advertisers. The tool works similarly to Performance Max but adds advanced generative features; it automatically crafts headlines, images and audience targeting based on your goals. Early adopters can enable it by checking the “AI Max” box within the Google Ads interface. If you’re running holiday promotions, turning on AI Max could increase sales without additional ad spend.
Trusted Vendors and Accounting Automation
The Xero report highlights that many business owners hesitate to adopt AI because of data privacy and accuracy concerns. One practical way to start is by using AI within trusted, industry-specific platforms you already rely on. For example, cloud accounting software like Xero or QuickBooks now includes AI features that automatically categorize transactions, forecast cash flow and draft invoices. Because these tools are built on secure financial data and subject to stringent regulations, they provide a safer on-ramp to automation. Review the back-office tasks you still perform manually and check whether your current vendors offer AI extensions.
What This Means for Your Business
The convergence of training programs, new insurance products and smarter marketing tools signals a turning point for small businesses. Events like the AI Jam show that hands-on education can demystify AI and empower entrepreneurs to build bespoke solutions. At the same time, the surge in AI-generated content and decisions introduces legal and reputational risks, making specialized insurance increasingly important. Meanwhile, AI-driven marketing platforms like Constant Contact and Google’s AI Max prove that the benefits aren’t limited to big budgets.
Here’s how these trends translate into real-world outcomes:
- Faster experimentation. Building your own assistant at an AI Jam or through tools like ChatGPT lets you test ideas without hiring developers. You can iterate quickly and move on if something doesn’t work.
- Reduced risk. Securing AI-specific liability coverage helps ensure that mistakes made by automation don’t jeopardize your business. Think of it as a seatbelt for your digital initiatives.
- Improved customer reach. AI-powered marketing tools free up time while optimizing campaigns, so you can focus on relationships instead of juggling spreadsheets.
- Bridging the readiness gap. By starting with trusted tools and seeking training, non-technical founders can join the AI wave and avoid being left behind.
Take Action Now: Your AI Checklist
- This week: Choose one repetitive task and experiment with a general-purpose AI assistant like ChatGPT or Claude to see how it can save you time. Document what works and what doesn’t.
- Within two weeks: Audit your insurance policies and consult with a broker about AI-related endorsements like Counterpart’s coverage. Understanding your risk exposure early helps you avoid future surprises.
- By month-end: Activate AI-powered marketing features in your existing tools. Test Constant Contact’s campaign generator or enable Google Ads’ AI Max experiment to boost seasonal sales.
- Ongoing: Keep an eye on community events such as the Small Business AI Jam and sign up when they occur. These workshops are invaluable for building confidence and networking with other entrepreneurs.
Ready to Embrace AI?
AI adoption isn’t about becoming a tech guru overnight; it’s about using smart tools to reclaim your time and grow your business. Late November’s news cycle delivered a clear message: resources and protections are expanding, and the barriers to entry are lower than ever. Whether you attend an AI Jam, tick a new box in your Google Ads account or call your insurance broker, small steps today can compound into big gains tomorrow. Keep experimenting, stay curious and share your experiences — the SoloAITool.com community is here to support you on your journey.
