In 1999 the press ran stories that Massow wanted to have a baby with gay comedienne, Jackie Clune, but this never happened. Massow explained that it would have been "unfair on the child". Massow has fostered three children, and is seen as an urban dandy (with celebrity friends). His flatmates were for a time were Conservative columnist, now Tory front-bencher, Michael Gove and head of Tory policy and Conservative London Mayoral candidate Nicholas Boles MP, a situation Massow described as "Tory Friends".
Massow's status in the gay community was severely damaged by his public support for Fox Hunting — he has been field Hunt Master and Joint Master of the Cokeham Bloodhounds. He has also owned race horses. He was a founder member of the ‘No Euro’ campaign, but has since publicised his support for the Euro (most recently as guest political editor New Statesman, May 2007).
In 1990, Massow started a financial services business from a squat in Kentish Town, north London, because he couldn't find funding for his idea. Having worked in the industry, he was able to source ways for gay people to take up mortgages and insurance at equal rates; rather than suffer the standard rejection, or massive increases in premiums that were levied by every insurer. Massow did this by researching how the various insurance computer ‘automatic underwriting systems’ operated. He then smuggled clients through the maze. If a homosexual fell outside of these computerised anomalies and were underwritten by an employee of the company, rejection was the most likely outcome (and with that the loss of any hope of buying a home) or huge premiums levied, usually making a mortgage unaffordable; especially when you factor in interest rates at almost 16%. It must be remembered that life cover was a mandatory requirement for people applying for a mortgages (for most companies) until as late at 1997. The first company to relax the requirement for life assurance was a division of the Cheltenham and Gloucester building society in 1994.
Critics say that he was just cashing in on the "pink pound" to become a millionaire. Others say he created the idea of the pink pound. Regardless, Massow is still remembered by the gay community as someone who successfully confronted the major companies to offer solutions at a time when no one else dared to be associated with this community. His firm became the 10th largest IFA in the UK by 1997, valued by Catalyst Fund Managent Ltd at £22m, a VC company which owned a 26% share in the business.
Massow also had a high profile failure. Among many ventures, he was an investor in the magazine Phaze in March 1994, but the venture collapsed and was, as Massow himself joked, "just a phase". In 1996, venture capitalists Catalyst invested in Massow Financial Services. By doing so, Massow secured his company's reputation as the premier supplier of financial services to gay men and women. In 1999, the firm entered into a reverse-takeover with company Rainbow Finance (its main competitor), as Massow sought to reduce his day-to-day involvement. Rainbow Massow later collapsed, and in 2001. Massow returned to the business to rescue the business, returning it to profitability, which he later sold to his employees for just £100; fulfilling his ambition to reduce his involvement, and by way of thanks to staff who had withstood the roller coaster ride of an unsuccessful merger followed by a later disastrous partnership with Zurich Life, still being argued about in the High court at Bristol.
In addition to many media appearances (having been the entrepreneurial 'expert' in magazines such as FHM and Esquire through to TV shows such as the Big Breakfast and Richard and Judy), in autumn 2005 Ivan Massow entered into a one year challenge on the Channel 4 television series Make Me A Million; acting as investor and adviser to a start-up business, Halos n Horns; a children's shampoo. His competitors were Emma Harrison and Chris Gorman. Massow won the challenge as his business was selected by the judges, Luke Jonson and Stelios Haji-Ioannou, as the most valuable and with the highest prospects for growth. The judges were impressed by the fact that Halos and Horns had already become the UK's second largest children’s shampoo manufacturer, even before the programme had been aired.
Although the idea had been given to Massow by his hairdresser, Joe Mills (who was rewarded with shares), the company and its success are credited to Leila Wilcox the MD, around whom the concept and branding Massow had modelled. She remains the active party and face of the brand. Since the sale of the business to Ceuta, Wilcox and Massow remain friends and are developing new business concepts.
Massow had been active on gay issues. The Conservatives had seemed a strange choice, but Massow, despite his reasons for becoming re-involved, supported them on economic matters and felt that the Labour Party had its fair share of homophobes. Moreover, he wanted to put issues of intolerance, such as homophobia, behind them and end discrimination across the spectrum of political parties. However, he felt that his erstwhile friend William Hague's support for Section 28, a measure preventing the promotion of homosexuality in the classroom, was a step in the wrong direction. Many espousing "compassionate conservatism" were tested by this policy and other gay rights matters, leading to the defection of Shaun Woodward MP to Labour and John Bercow MP's resignation from the frontbench. Likewise Massow wanted to shame the party into change.
Massow failed to change the party as he'd hoped and finally did this by following Woodward into the Labour Party in 2000, where he was welcomed by longtime friend Mo Mowlam. Indeed, there was a large amount of press interest in his change of party, despite him having never held elected office or even stood for Parliament. However, his time in Labour was short-lived, he had no party political ambition. He resigned and attempted to stand again as Mayor of London in 2004 with his own movement " Change London", although his name in the end never made it onto the ballot paper, his ‘Change London’ campaign brought to the attention of the government and the mayor's office the potential long term effects on business of under-funding in transport and crime prevention. These were later incorporated into the Mayor's own campaign manifesto.
By February, Massow had resigned, forced out by the ICA Council. Subsequent interviews with Massow revealed that this was likely anyway, given his uncomfortable relationship with the ICA Director and his views on art. He has described the art world as bitchy and superficial, although he claims to actually like much conceptual art and acted in order to redress the imbalance between support for conceptual and "traditional" arts in the British art scene.
Massow subsequently set up the Institute of Contemporary Culture, a forum for artists supposedly free from "orthodoxy".
Massow frequently writes in the UK press; from articles in broadsheets, including features in the Guardian or the Daily Telegraph and the 'Thunderer' column in the Times, to being an occasional comment writer for broad-sheet newspapers and magazines ranging from the New Statesman and The Spectator to FHM and GQ. He currently writes a monthly business advice column in Esquire magazine.
Massow makes regular appearances on national television, from being the 'Entrepreneurial Expert' on Richard and Judy to shows such as Mariella Frostrup, BBC's Question Time and Newsnight. He was the subject of Inside the Mind of a Millionaire, a BBC documentary about entrepreneurship which featured his prison work. He was also the winner of Make Me a Million on Channel 4 in November 2005, a competition between 3 teams led by prominent entrepreneurs to 'make a million' in a year from a start-up company.
Ivan is also a regular spokesman on national TV and radio on subjects from finance and gay rights to culture and mental health issues. Ivan is also regularly invited to speak at conferences and public meetings on entrepreneurship, human rights, art and social inclusion within the work place.
Charity involvements and initiatives include founder/sponsor of ‘Insurance for Survivors’ – a coalition of four major charities whose aim is to increase awareness within the financial services industry of the problems encountered by survivors of mental health issues, cancer and major transplants. He was Chairman of MIND's inquiry into mental health and social exclusion and creator / coordinator of a Pre-Release scheme helping prisoners to start businesses for the Prince’s Trust. This led to Massow giving lectures at Feltham YOI to prisoners interested in entrepreneurship.
He is a member of the ‘Entreprenologists’, a group which investigates what defines an entrepreneur and how government can encourage/assist entrepreneurship in the UK. He is a Trustee of the ‘Entrepreneur’s Working Party’, a DTI/Treasury inspired initiative. This position inspired him to approach the Prince’s Trust to create the prisons programme.
Massow is also creator/sponsor of the ‘Jake Network’ (www.jaketm.com), a social/professional network in the UK which holds over 300 events a year in London for gay professionals, though he is known to keep a low profile and rarely attends events.
Massow was a Patron of REGARD – a charity/support group helping gay people with physical disabilities. He founded of the April Bombing Appeal which raised cash for victims of the nail bombs in Soho, Brixton and Brick Lane in February 2000, raising cash to provide wheelchair access in homes and financial support for people unable to work as a result of their injuries.
Massow was a founder member of the ‘Me Too’ anti-violence campaign with Elizabeth Vallance, Rabbi Julia Neuberger and Lord Saatchi. The campaign aims to provide a voice for people who want to promote social, racial and cultural difference as part of the UK national identity.
Massow was a former member of the Samaritan’s central marketing/fundraising team working on the Ambassador’s Project and is a trained Samaritan. He is involved in a number of social and charity organisations and campaigns and a consultant to committees such as Stonewall and GALOP. He is Patron of the Salon des Arts – a gallery devoted to giving unknown artists a stage.
In the past Massow has sponsored a number of organisations including the Covent Garden Arts Festival, Stonewall FC (1st and 2nd teams) and the Terrence Higgins Trust, as a ‘Friend for Life’. Massow was the main sponsor for the 2001 Stonewall Equality Dinner at the Savoy. He has also sponsored many gay pride events around the UK.