(This column originally appeared in Forbes)
Welcome to The Main Street Tech Report, your weekly roundup of the most important small business technology news. Here are five key developments in AI, automation, and digital tools that emerged this week-and what they mean for your business.
How to Switch from ChatGPT to Claude for Your Small Business
If you’re a ChatGPT user thinking about making a change to Anthropic’s Claude, the process is pretty easy according to Ruben Circelli of PCMag. Users can migrate their information stored on ChatGPT to Claude — search history, preferences, and instructions. A ChatGPT user, Circelli walks the reader through the process starting with opening the settings page in Claude, navigating to the Capabilities tab, then clicking the Start Import button in the memory section at the top. Circelli notes that Anthropic has stated the “memory imports are experimental” at this point with examples of data that wasn’t stored on Claude such as deep-dive reports and applications. (Source: PCMag)
Why this is important for your small business:
You know how there’s a periodic tech darling that everyone loves? This month it’s Claude. It’s Claude Code offering has taken off with many businesses and — very interestingly — I’m seeing a growing number of my small and mid-sized clients creating mini applications with it with most being connectors into their company data for analysis. The reports are very positive — Claude Code is easy to use even for the luddite technologist. But by no means has Claude won the AI race. ChatGPT has more tricks up its sleeve, coming soon and Google’s been quietly lately. Just wait…
Microsoft Copilot Accuracy Concerns for Small Businesses
Copilot users — a disclaimer from Microsoft has surfaced about the AI’s accuracy. Per the Terms of Use update in October 2025, “Microsoft Copilot is for entertainment purposes only. It can make mistakes and may not work as intended.” The wording is curious as it doesn’t align with the company’s marketing of Copilot as a productivity tool — even for work. PCMag recently reported a clarification of the wording from an anonymous Microsoft source who claimed “entertainment purposes” is language that was used when Copilot was first launched as a search companion in Bing. Ultimately, it’s up to the user to determine how much reliability they invest in AI tools. (Source: Gizmodo)
Why this is important for your small business:
Microsoft has really got to get it together. Their messaging on Copilot is poor and its branding is even worse. Users have been disappointed. They have plans to scale back its visible presence and the company’s stock value has taken a hit. But then again it’s Microsoft, so I’m confident things will swing the other way. So don’t go throwing out your Microsoft software anytime soon.
How Bing Influences ChatGPT Recommendations and SEO
Writers Molly Nogami and Ben Tannenbaum ran an experiment to see how often search results appear on ChatGPT’s radar (list of recommendations) after performing a search with Bing and with Google. Based on the results they found that Bing is the biggest driver of which brands show up in ChatGPT answers. Using the query — ‘what are the best hotels in New York City?’ — they analyzed mentions, citations and SERPs (Search Engine Results Page) after entering the prompt 68 times. Notable results included: even if a hotel ranks number one in a Google search result, ChatGPT doesn’t pick it up as a recommendation. Traditional SEO success doesn’t guarantee an appearance in ChatGPT. Visibility and a hotel’s ranking in Bing strongly correlated with being mentioned in ChatGPT. They also discovered that mentions have more impact than citations. To read through their entire list of results and breakdown of metrics visit the link. (Source: Search Engine Land)
Why this is important for your small business:
I guess this shouldn’t come as a surprise as Microsoft is deeply embedded with OpenAI, despite their differences and recent arguments. The problem for businesses is that Bing is clearly not as popular as Google so if they spend for ads with OpenAI their reach won’t be as great.
Quicken’s New AI Financial Planning Tools for Entrepreneurs
Financial management software Quicken has debuted an advanced, all-in-one financial platform with AI integration, real-time data, and broader financial tracking to modernize personal finance management. Users can connect to their bank and review/ download transactions from their checking or savings account — as Quicken is connected to more than 14,000 financial institutions; budgeting tools provide financial analytics for planning; investment tools offer real-time data for users looking to build investment portfolios. The software also includes a goal setting tool to give users a detailed roadmap to their financial growth. Users can also keep track of their bills with Quicken’s integrated bill management system. “…comprehensive account aggregation, sophisticated budgeting, investment oversight, and tax preparation capabilities provides an unmatched foundation for financial success,” the company stated in its press release. (Source: openPR)
Why this is important for your small business:
There are millions of small business owners using personal financial software like Quicken and Mint to manage their money. The best approach — for a number of reasons — is to always have a separate set of books for your business. But if you’re a sole proprietor that approach isn’t always realistic. For those owners I recommend managing all your money on a personal financial too while ensuring that you’re breaking out business and personal transactions (which you’re able to do on these platforms). Then take advantage of their AI and planning tools.
AI Website Builder Kite Simplifies SEO and Maintenance
Kite — the new AI website builder developed by San Francisco tech company Appsmith — automatically maintains, fixes and optimizes websites over time, freeing up small business owners and freelancers from time-consuming website management. According to its developers, Kite “walks people through the design process” and automatically monitors and fixes issues without the need for human assistance. The platform is reportedly gaining traction as its capabilities for ongoing site management is significant especially for those new to website creation. Launched this month, Kite is a shift from building a website to running a self-managing website that eliminates the extra cost of hiring a web developer. (Source: San Francisco Today)
Why this is important for your small business:
I have a great web developer but I wonder what lies in the future when there are products like this. My take is that great tools like Kite can help reduce costs and eliminate hours being spent by a web developer. But someone has to own the system and use it to make changes and I don’t see that being fully automated anytime in the near future.
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