Ivan Massow opens the door to his late 19th-century house, on the corner of London’s hip Hoxton Square in the East End, with a sheepish grin. He knows what’s coming. On entering the three-storey building, a former printworks, you walk into a huge space that stretches down to an open-plan kitchen at the end. A large glass chandelier dominates the room and portraits line the walls. Portraits, that is, of Ivan Massow.
“Now, I know you’re going to take the piss out of me,” he says presciently. “Bizarrely, there are fewer at the moment than there usually are, because some have just gone off to be entered into the BP [Portrait] Award.”
Even so, I count 11, including two painted by society portraitist Jonathan Yeo, of Massow – entrepreneur, financial adviser and, briefly, candidate for mayor of London – stark naked. “One was painted when I was fat; the other was done thin,” he says. “I’m continuing a collection of portraits that I began when I was younger. I’ve always loved portraits, and when I was head of the ICA [the Institute of Contemporary Art], people asked to paint me all the time.”
Five more are being painted at present, and one sculpture, bringing the total close to 30. “It is most embarrassing; it’s becoming a problem,” he laughs – he’s aware of how ludicrous it looks. “I love it, and, in a weird sort of way, it is my own art, isn’t it? For Tracey Emin and those sorts of people the art is all about them all the time. What you are buying is an insight into the artist, or some connection they have with the world that is inspiring and, in its way, beautiful. The relationship between the artist and the sitter has always fascinated me, and, as it started to grow, I thought I might just keep this up and get a couple each year.”
It might seem strange that someone who was renowned for damning conceptual art as “pretentious, self-indulgent, craftless tat” should now be embarking on his own contemporary art project. Yet Massow has always supported young artists, even back in 1990 when he launched his financial advisory firm for the gay community out of a London squat. He paid bursaries of £400-a-month to young artists to “keep them out of McDonald’s”. Indeed, despite having cultivated or, as he qualifies, having allowed the media to cultivate, an image of himself as a school leaver with no qualifications, in fact he completed two years of a foundation art course.
“I just felt that art was going in a wrong and superficial direction,” he says now. “I felt people were deliberately making tat just to appeal to a new genre, and that the emperors were wearing no clothes.”
Massow directed most of his venom at Emin, something he freely admits was “for headlines”. At the time he said she “couldn’t think her way out of a paper bag”. Now he merely dismisses her as “a bit dull”, before pausing and adding, “she really has a sense of herself born out of those early pieces”.
That’s one thing Massow could not be accused of. His life has had more twists and turns than that of the soap characters played by his close friend, the actress Joan Collins, including themes of what some have seen as passion and others as betrayal.
He first came to prominence as the darling of the gay community for being the one financial adviser offering insurance to people who were HIV positive. Young, good looking and the antithesis of the camp caricature of homosexuality that was prominent in Britain at the time, he was snapped up by the media as the go-to gay of the 1990s. Yet he quickly fell out of favour when he came out as a Conservative, squiring former prime minister Margaret Thatcher very prominently around the 1999 party conference. The sense of betrayal was palpable – and almost turned violent.
“The hate mail I got from gay people was phenomenal,” he says, as we wander from painting to painting. “I also received death threats from the right wing as well. I had the bomb squad out three times.”
And then, just to ratchet things up even further, in 2000 he jumped ship and joined the Labour party, before flip-flopping once more and rejoining the Tories. So now, I say, gay people don’t trust you, and the Conservatives don’t trust you. Is there anyone who does? “I don’t know. My mum – and my dog,” he adds, a little disconsolately.
Even now he cuts a polarising figure. A few nights before we meet, he’d been in the local pub and three gay men had walked out, shouting, “You shouldn’t be allowed in here, you f****** Tory.” “That sort of thing can be very hurtful,” he says. “I’m shocked sometimes just how violently people react.”
But even so, Massow is stirring himself to return to the front line, both in terms of media exposure and political activism. He’s got four programme pitches about entrepreneurialism with the UK’s television networks, and he’s back on the Conservative party’s approved candidate list.
He has also launched a new company, Paymemy.com/mission, which aims to scoop up the annual commissions paid by investors to their financial advisers and distribute the cash back to the customers. The early signs are positive: one day’s advertising brought in 10,000 new clients, Massow says.
It may need to be successful – he’s a keen philanthropist, giving away between “£25,000 to £100,000 a month”, he says, but in a very low-key fashion. “These are all small amounts. It could be an artist needing a bursary, someone wanting to get a play off the ground or a friend seeking university fees. I tend to get an awful lot of approaches.”
He will receive even more after this, I suggest. “But it is the biggest pleasure you can have,” he says. “I just get paranoid I won’t have enough to retire on. But then I go out and do another deal and it all comes together again.”
Having himself been adopted and fostered, Massow has also signed on as a mentor with charity Action for Children. “I can’t tell you how excited I am,” he says. “What’s nice about this mentoring scheme is that you become one of the few consistent things in a child’s life.”
But beyond business and philanthropy, politics remains his true passion. “I am a complete and utter [David] Cameron-ite,” he shrugs. “He hasn’t put a foot wrong; I am in awe of him.” And while becoming prime minister is probably now out of his reach, one political position still appeals – but good luck getting him to admit it.
So, are you going to be standing for London mayor? I ask. “Honestly, it is something I could not talk about. I don’t ... I have no plans at the moment to get involved.” Why are you dodging the question? I ask. It makes me think he is already in talks. “Who knows?” he answers, mischievously or mysteriously – probably both. “People are always talking to me about it, because of course it would be an interesting role, but I don’t at the moment know whether it is feasible.”
That’s not a blanket no, then? “Have you ever heard me say no?” he laughs.
It would be the dog, Taxi, but then I’m not really a possessions sort of guy. I know it sounds weird, but there’s also a Jonny Yeo picture of Tony Blair that he allowed to be done. He sat for the government collection and Jonny did two. I love the piece and I love what it meant at the time , because it was another landslide and everything about New Labour was still fresh and really meant something. One day Blair’s got to do something right [he jokes]. Every time he does something else in the papers I just curse him for reducing the value of my picture.