Almost ten years ago, in 2017 I referenced an article appearing in the online publication, Next Avenue, www.nextavenue.org , where the subject was “At What Age Are You Too Old to Manage Your Money?” Fast forward to 2026 the same online publication, Next Avenue, raised an entirely different, but related, issue. Today the question raised is how senior entrepreneurs use AI to their advantage. The surprising conclusion contained in the recent March 2, 2026 article is that, because of their background and experience, some seniors may actually find they can be ahead in dealing with the Al age. See “The Secret Advantage Older Entrepreneurs Have With AI”
This turnabout is surprising. In the first case in the 2017 Next Avenue publication the question was whether persons in their sixties, seventies and above are capable of managing their own funds. It assured older persons and their families that elders not affected by other disabilities can do that and distinguished the types of planning. The second implies that past experience is a plus. What is the difference? I would suggest that the current article targeting entrepreneurs
specifically is dealing with a new type of individual, the senior entrepreneur, and asserts that experience matters even today, maybe even especially today.
Next Avenue in its recent article tracks, among others, a solo entrepreneur, Barbara Roos who launched her consulting firm, Trailhead Communications, when she turned 50 years old. It goes on to state “ she hired a research team, a marketing department, and an IT help desk. Sort of…”
IT was one answer. Roos herself stated “ as a solo founder, I don’t have any of those things: research team, marketing department and IT help desk… Al extends my capabilities across all of those roles without replacing my judgment or experience…”
The article goes on to state that Roos is not alone but is part of a “quietly growing group” of 50+ entrepreneurs who learned that everything they lived through makes them well-equipped to harness artificial intelligence into their new businesses.” In other words experience matters.
From my own experience in dealing with clients I might note that the unusual circumstances under which we have all been living since before COVID and then beyond have created a climate where sometimes it is appealing to go into business on your own and sometimes it is verging on necessity. For people who have been laid off from their jobs and for those who realize that retirement could run many years while they need additional income, entrepreneurship could be one answer among others. It does, however, take a special kind of person to go out on her or his own and work through the challenging job of managing a business.
Here are some examples.
Erica Wood of “Client Journey Advisors” described her flexibility in adapting to changes over the years as a plus and stated “I was working when email replaced fax machines, when CRMSs changed how we managed relationships, and when remote work reshaped how teams collaborate.” Her background was healthcare and professional services before she went out on her own. She noted that AI was the next step. She used her background in dealing with people face to face combined with AI as a “thinking partner” to draft client “journey maps” and related but saves the final decisions, narrative and high stakes conversations for herself. She recognizes that “trust is built in nuance, tone and timing.” She notes that AI supports but does not replace those qualities.
Eugene Lebedev, the managing director of Vidi Corp., a company that built a custom version of ChatGPT that turns long-form blog posts into a series of LinkedIn posts, states he saved about $10,000 a year and then “created a custom AI tool that writes blog articles optimized for Google.” He said that the greatest lesson he learned is that AI performance “improves dramatically” with context. He noted that, over time, it begins to function like a staff member that “knows your business.”
Andrea Nero who came from an academic background observed that some consulting firms charged nonprofits huge amounts and there was a less expensive alternative which she designed.
All of these new senior entrepreneurs deserve credit for their patience and creativity. Good to know they exist and are recognized for the work they are doing.
