Can I beat ChatGPT in picking great dividend shares to buy?

How good is AI when it comes to picking dividend shares for the next five years? Stephen Wright is on a mission to find out.

| More on:
Concept of two young professional men looking at a screen in a technological data centre

Image source: Getty Images

When investing, your capital is at risk. The value of your investments can go down as well as up and you may get back less than you put in.

Read More

The content of this article is provided for information purposes only and is not intended to be, nor does it constitute, any form of personal advice. Investments in a currency other than sterling are exposed to currency exchange risk. Currency exchange rates are constantly changing, which may affect the value of the investment in sterling terms. You could lose money in sterling even if the stock price rises in the currency of origin. Stocks listed on overseas exchanges may be subject to additional dealing and exchange rate charges, and may have other tax implications, and may not provide the same, or any, regulatory protection as in the UK.

You’re reading a free article with opinions that may differ from The Motley Fool’s Premium Investing Services. Become a Motley Fool member today to get instant access to our top analyst recommendations, in-depth research, investing resources, and more. Learn More.

I asked ChatGPT to pick me a portfolio of five UK dividend shares. And just to make things interesting, I’m going to compare that with a portfolio of five income stocks selected by me.

Starting today, I’ll track both, see what happens, and report back with the results in due course. I’m not putting my own money behind what ChatGPT says, but I’ll be keeping score.

The portfolios

Right then, let’s get to it. The rules are pretty straightforward – dividends are reinvested back into the shares of the companies they came from and the highest total return wins. 

With that in hand, let’s get to the portfolios. Since ChatGPT gave me suggested weightings for each position, here are both portfolios with percentage allocations for each choice:

ChatGPTStephen Wright
British American Tobacco (22%)Admiral (22%)
M&G (22%)Games Workshop (22%)
Shell (20%)Croda International (20%)
Unilever (18%)Diageo (18%)
OSB Group (18%)AEW REIT (18%)

In both cases, we’ve mostly stuck to the FTSE 100 for ideas, but each team has an outsider. ChatGPT’s gone for OSB Group (LSE:OSB) and I’ve selected AEW REIT (LSE:AEWU).

Having seen the teams, I’m feeling pretty good. But I didn’t expect to see OSB Group making the list, so let’s have a closer look at the wildcard on Team ChatGPT.

OSB Group

OSB’s a specialist mortgage and savings business. It works a lot like a bank – taking in deposits, making loans, and earning a profit on the difference between the interest rates.

It specialises in loans for Buy-to-Let investors, developers, and commercial properties. Its focus in this area can give it an edge over more general competitors in terms of assessing risks.

Its lending margins have been pretty strong, but they’ve been starting to come down recently. This is due to higher interest rates increasing funding costs, which is a risk worth noting.

At the moment though, there’s a dividend yield of around 6% on offer. But while I’m interested in taking a closer look, I don’t think I like it as much as anything I’ve chosen.

AEW REIT

The wildcard in my portfolio is AEW REIT – a real estate investment trust (REIT) that doesn’t play by the usual rules. And it could just be the ace up my portfolio’s sleeve.

Please note that tax treatment depends on the individual circumstances of each client and may be subject to change in future. The content in this article is provided for information purposes only. It is not intended to be, neither does it constitute, any form of tax advice.

Conventional wisdom says REITs are supposed to focus on properties with long-term leases in high-demand industries. That’s the usual way to try and achieve consistent rental income.

AEW focuses on unpopular sectors where demand’s weaker, but supply’s also low. And it looks for leases that are closer to expiry as potential opportunities for rent increases.

It’s a high-risk strategy with a much higher chance of vacant buildings. But the company’s executed incredibly well on its strategy and I think income investors should take a look.

Smart money

This particular competition is just for fun. I’m not willing to put my own money behind a portfolio generated by ChatGPT, especially when it contains a name I don’t know very well.

I am however, interested to see how the two portfolios get on. I’ll set up a simulation using my broker’s online platform – watch this space for future updates.


Should you invest, the value of your investment may rise or fall and your capital is at risk. Before investing, your individual circumstances should be assessed. Consider taking independent financial advice.

Stephen Wright has positions in Diageo Plc, Games Workshop Group Plc, and Unilever. The Motley Fool UK has recommended Admiral Group Plc, British American Tobacco P.l.c., Croda International Plc, Diageo Plc, Games Workshop Group Plc, M&g Plc, and Unilever. Views expressed on the companies mentioned in this article are those of the writer and therefore may differ from the official recommendations we make in our subscription services such as Share Advisor, Hidden Winners and Pro. Here at The Motley Fool we believe that considering a diverse range of insights makes us better investors.

More on Investing Articles

Road 2025 to 2032 new year direction concept
Investing Articles

£20,000 in BP shares can net investors a £1,232 second income…

BP shares have been bumpy lately but there's a terrific dividend income stream on offer and Harvey Jones says it…

Read more »

Front view of aircraft in flight.
Investing Articles

Rolls-Royce shares just got an Outperform rating

A 10% dip in Rolls-Royce shares since September hasn't deterred one analyst team from giving the FTSE 100 stock a…

Read more »

Night Takeoff Of The American Space Shuttle
Investing Articles

3 FTSE 250 shares to target a 14.8% annual return

Discover which FTSE 250 growth shares have torn higher over the last decade -- and why Royston Wild thinks they…

Read more »

Middle aged businesswoman using laptop while working from home
Investing Articles

I asked ChatGPT to design a 5% yielding passive income ISA from 5 FTSE 250 shares and it said…

Harvey Jones asked artificial intelligence to create a passive income stream from a balanced portfolio from medium-sized UK companies. The…

Read more »

Snowing on Jubilee Gardens in London at dusk
Investing Articles

Will the stock market crash before Christmas?

Christmas is fast approaching. Could the uncertainty in the markets lead to a stock market crash before presents get opened?

Read more »

Portsmouth, England, June 2018, Portsmouth port in the late evening
Investing Articles

What will happen to the UK stock market in 2026? Here’s what experts think

UK stocks have had one of the best years of the century, but can that momentum continue into 2026? Our…

Read more »

Illustration of flames over a black background
Investing Articles

Why are investors on this trading platform piling in to an AI-threatened US stock?

James Beard tries to work out why this US stock’s attracting a lot of interest even though it could be…

Read more »

piggy bank, searching with binoculars
Investing Articles

Prediction: in 12 months the Persimmon share price and dividend could turn £10,000 into…

James Beard examines whether the Persimmon share price could stage a major recovery in 2026. And he looks at the…

Read more »