Matt Fleming: “I’d like to think that if I’m going into a meeting, people are pleased to see me.”

As the face of MarketCast, Executive Chairman of AF Oliver and “eternal optimist”, Matt Fleming is a busy man. Here, he talks to Housing View about starting a £60m company from his business partner’s bedroom, his market predictions for the next few months…and those shirts

by Ben Wakeling

Matt Fleming has a dilemma. He has been asked to speak at the Housing Market Intelligence conference in October, and he is unsure whether he should wear one of his jazzy shirts.

‘Those’ shirts are quickly becoming his trademark; at a recent board meeting with an independent developer, a “slightly nervous” Fleming entered a theatre-style room wearing a plain pink shirt, and was greeted by two investors.

“They came over and shook hands, and one of them said to me, ‘Where’s your crazy shirt?’,” he laughs. “It did make me chuckle.”

It all began when Fleming started uploading his MarketCast series to YouTube in March 2022, in which he gives his expert analysis of the housing market along with various predictions (he is particularly proud of forecasting that the inflation value in April would begin with an 8, which it did).

Fleming wears a simple striped outfit (“not intended to be a crazy shirt,” he adds) in the inaugural broadcast of MarketCast, and – along with positive feedback on the analysis itself – found himself receiving several comments asking where his shirt had come from. I’m onto something here, he thinks.

Now, thirteen episodes later, Fleming has a whole wardrobe full of colourful shirts, which he insists on wearing only once. He’s considering auctioning them off for charity one day; his favourite, by the way, is one with blue butterflies.


Fleming is speaking to me from his home in Wimborne, a few miles north of Poole, settled in his home office in front of a bookcase boasting shelves bursting with Britannica encyclopaedias and other compendiums. Buried somewhere amongst the books and journals are his diaries from 1985, when he started Aylesworth Fleming – a marketing agency – from the back bedroom of his business partner, Martin Aylesworth Syvertson, on a “very dodgy street in Bournemouth.”

Martin Aylesworth and Matt Fleming: 1985 versus 2015.

Eventually, they took out a 25-year lease on a small 675-square-foot office on Poole Hill and, over time, leased further office space in the same building before eventually expanding to the point where they had to move out in 2012, having fulfilled the lease and extended it by a further two years.

It wasn’t all plain sailing, though. During the financial crash of the nineties the firm very nearly went bust. Fleming bought out Aylesworth – who returned to the States – and, with the support of three people (“all of whom are great friends to this day”) as well as Cala Homes, who paid in advance for a few months, was able to save the business from going under.

There have been some memorable moments along the way. In 2019, following the merger of Linden and Bovis, Fleming and Rachel Asquith, Aylesworth Fleming’s MD – concerned that their working relationship with Linden could end – managed to secure a crisis meeting with Bovis CEO Greg Fitzgerald, who mentioned that the business was trying to work out what to call the newly-combined group. Seeing an opportunity to impress, Fleming offered his services.

“I remember saying: ‘Yeah, I’d love to do that’; I was thinking, I’ll go home, do a bit of research, fast track it and come back to them in a couple of weeks, so I asked Greg: ‘What’s the deadline?’ He said: ‘I’ve got a meeting tomorrow at noon.’”

That night, back in Bournemouth, fuelled by a takeaway and “two or three bottles of very fine red wine”, Fleming and his colleague came up with two options, both a portmanteau of Bovis, Linden and Galliford Try: Bolin, or Vistry. The following evening, they received a call from Fitzgerald; the board had decided to go with Vistry. Oh; and Aylesworth Fleming could continue their marketing partnership.

By the time the business was sold three decades after its formation, in 2016, it had grown from humble beginnings with four-figure seed capital into a £65m group employing more than 250 people.

A lot of those old sales skills have been lost, because they just weren’t required

There are no real secrets to success, Fleming says, although he is beginning to pull a book together called ‘How to Build an Agency’. Really, it comes down to luck, relationships – and, ultimately, being fun to work with.

“Always have your client looking forward to you getting to a meeting,” he says, adding that he encourages his team to always turn up to meetings with at least one new idea, or take something innovative; but, most of all, “to take energy.”

“You can be either a zapper or a sapper,” he remarks. “A zapper is someone who zaps a meeting with energy; a sapper is someone that just sucks the very oxygen out of a room. I like to think that if I’m going into a meeting, I get the sense that people are pleased to see me when I get there.”

Now, following a brief retirement, Fleming is back where he began, as Executive Chairman for AF Oliver, rolling his sleeves up and attending regional marketing meetings following a turbulent two years for the housing industry, which finds itself reeling from “the silly nonsense that went on in September”.

“It’s easy for people to generalise about the market and forget the day-to-day issues that Sales Directors face,” he says. “We’ve suddenly moved from eighteen months of nobody really having to work very hard to sell, developers being six months forward sold…then the world changed, and a lot of those old sales skills got lost, because they just weren’t required.”

Now, he adds, developers need to catch the falling knife sooner rather than later and reduce prices; advice which can be the most difficult to give and receive. “Other people might not be brave enough to tell you to do that, but sometimes you’ve got to grasp the reality.”

Fleming’s house price forecast for the rest of the year? “You heard it here first,” he remarks, “but we will see another increase in the average price in September. That doesn’t mean the annual rate of inflation is going to move into positive territory – it’s not, I don’t think we’ll see that again this year – but the average price is going to uptick in September.” (He promises me that I can ring him up and “call him a tosser” if he’s wrong.)

Any longer-term predictions are ludicrous, Fleming says. In fact, he has a family tradition every Christmas – “after the lunch, and probably a bit too much wine” – where he digs out a leading estate agent’s five-year predictions from five years ago. “About as much use as an ashtray on a motorbike,” he says, before adding that his wife and elder daughter both work in property, so are just as interested as he is…probably.


When he’s not dispensing advice, attending meetings or predicting the market, Fleming is active on LinkedIn (he tends to avoid Twitter, which he describes as “like standing up in the trenches and lighting a cigarette”), supporting colleagues, commenting on industry developments and boycotting Jameson whiskey following news that distillers Pernod Ricard have restarted exporting the liquor to Russia (Redbreast and Green Spot are fine replacements, he says; he only drinks Irish).

Will the man with boundless energy and ‘eternal optimism’ – according to his Twitter bio – ever retire? Yes, he says, but he already has a project in mind: to map out all the acquisitions and movements of key developers over the last forty years, and complete his book.

So, back to Fleming’s original conundrum: should he wear a jazzy shirt for the HMI conference? Give the people what they want, I say; they want the shirt. You don’t want to come onto stage to a chorus of boos.

“It wouldn’t be the first time,” he laughs.

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