‘I’m transsexual, so I’ve always had a female brain, but a boy’s body,’ explains Kate Craig-Wood. Over the past three years, this successful entrepreneur has spent nearly £50,000 completing the transition from male to female.

Back in 2005 she reached a point where she was ‘suicidal’, knowing a change had to happen. It was only when she discovered facial feminisation surgery – a series of surgical procedures aimed to alter masculine characteristics – that her life changed. ‘I never wanted to be a woman with a man’s face, so when I found out about the surgery I realised my dream was possible.’

The procedure cost £22,000 and she had to fly to California to undergo the surgery. This included having her forehead and jawbone broken and re-shaped, an upper lip and eye adjustment, and nose job. ‘For two months afterwards, I looked like I’d been in a car accident.’

When Craig-Wood removed the bandages she didn’t recognise herself. ‘It looked really terrible at first. But as the swelling settled down, this new face became visible. The surgeon had given me the face I should have had, I looked just like my mother did when she was my age.’ Within this three-year period she has also spent over £20,000 on implants and genital surgery.

Identifying with business

For Craig-Wood, entrepreneurialism has always been in her blood (her father founded the IT company Alphameric). ‘When I was growing up the dinner conversations always revolved around business. My father was a big inspiration and I knew from an early age that’s what I wanted to do.’

Having started out in IT as a man and emerged on the other side as a woman, Craig-Wood has a unique insight into the different ways the sexes behave and are treated in the world of business.

‘The biggest double-edged sword of my transition has been the change in how I’m perceived. I’ve been fortunate enough to afford good surgery, so I’ve had the really weird experience of becoming progressively more attractive and simultaneously finding it more difficult to establish credibility. I’ve found myself having to repeat points before male counterparts stop staring at my chest.’

Battling the stereotypes

So does she believe there is an inherent sexism in the business world? ‘When I was growing up, I was always encouraged to become an entrepreneur but my sister wasn’t. I do feel that I have been advantaged by my upbringing as a boy. What we need in boardrooms and technology teams are more women. There’s a lot of research to suggest that gender-balanced management teams work better.’

Getting women into IT is an issue Craig-Wood is passionate about. She recently became the first woman to tandem-skydive past Mount Everest to raise funds and awareness for the charity Computer Clubs for Girls. The total trip, which included a three-week trek through the Himalayas, came to £18,000. ‘It was absolutely exhilarating,’ enthuses the 31 year old.

‘As we ascended I was getting more and more nervous, when I saw Mount Everest framed by the door of the plane I was terrified. At first it was this horrible freefall feeling, but then the air starts to support you and it’s almost like you’re lying on a big bean bag. The fear just vanishes and the ground slowly becomes more detailed.’

Craig-Wood’s hobbies are traditionally male in character and she admits to always having had a passion for ‘toys’. ‘It’s one area I’m quite extravagant in. When the business was really starting to take off I bought a DB7 Aston Martin in 2008 to treat myself. It cost £22,000 – although I’ve probably spent the same again fixing it up.’

She has also spent £45,000 on a Desmosedici RR bike which can reach up to 230 miles an hour. ‘It’s the ultimate motorbike, although I doubt I’ll ever ride it at that speed. For me if something arises as the pinnacle of experience – like the sky-diving opportunity – I want to take it. The bike was rare as there were only a few months in which to put the deposit down, and just a couple of hundred issued in the UK.’

Since undergoing the surgery Craig-Wood believes it has not only had life-changing consequences, but has also impacted on her business. ‘I’m much more outgoing and confident now. As a man I was more dictatorial and grumpy. Once I was more comfortable with myself, I started talking at conferences and became a better promoter, which improved customer confidence. That gave us the edge over competitors. The big problem is that a lot of internet companies are just too faceless.’