In a quest for new investment strategies, one individual turned to ChatGPT, the popular AI chatbot, to explore potential avenues for generating a second income through the stock market. While seeking advice from generative AI may raise eyebrows among seasoned investors, the hope was that it could uncover valuable insights amid the vast amount of online information.
Upon inquiry, ChatGPT initiated the conversation by posing essential questions familiar to many investors: the amount available for investment, the desired time horizon, and the overarching financial goals. After providing input that reflected a typical investor profile—in this case, an investment range of £25,000 to £50,000 targeted over a 10 to 20-year period, with a dual focus on growth and income—the AI provided a structured response.
The AI emphasized the advantages of utilizing a Stocks and Shares ISA, particularly in light of impending changes to dividend tax rates, which are set to increase in April 2026. However, it was crucial to note that tax treatment may vary based on individual circumstances, and the information should not be construed as professional tax advice.
For an investment strategy, ChatGPT proposed a conservative approach comprising 60% in quality FTSE 100 dividend stocks, 30% in higher-yield assets, and the remaining 10% kept in cash reserves. The iShares UK Dividend ETF was recommended for those seeking easier diversification. ChatGPT also shared prudent allocation guidelines, advising against any one sector exceeding 25% of the portfolio and limiting individual stock exposure to a maximum of 6%.
Among the suggested FTSE stocks were Legal & General, Phoenix Group, and M&G, although the user felt that diversification could be enhanced by adding a utility stock such as National Grid or a solid real estate investment trust (REIT). In terms of higher-yielding stocks, ChatGPT identified Ashmore along with the renewable energy REIT Greencoat UK Wind.
While the strategy laid out by the AI was deemed basic yet reasonable, the user expressed some skepticism about the stock choices, particularly regarding high-yielding mid-cap stocks. A strong contender for the investment strategy was identified in Supermarket Income REIT (LSE: SUPR), a trust that focuses on critical retail and warehouse properties leased to major grocery chains like Tesco and Sainsbury’s.
This REIT is notable for its long-term, inflation-linked leases, providing a reliable outlook for rising rental incomes despite broader economic challenges. Its defensive nature stems from the essential demand for groceries, a sector that has shown resilience even during downturns. With a notable yield of 7.7% paid quarterly and consistent, albeit modest, annual dividend growth of 1% to 2%, Supermarket Income REIT presents a viable option for generating steady passive income.
Nevertheless, potential investors must remain cautious. The REIT’s dividend coverage is on the tight side, with earnings just sufficiently covering dividend payouts and cash flows covering only half of the requirements. While this situation is not uncommon within the REIT sector, it raises questions about sustainability; any stall in rental growth or an increase in financing costs could lead to potential dividend cuts.
Despite these risks, the trust’s history of eight consecutive years of dividend payments and seven years of growth fosters a sense of optimism for its future prospects. The exploration of investment opportunities continues, highlighting the necessity for individual diligence and thoughtful consideration in the pursuit of financial growth.


