Webb likes to think of himself as aggressive, but as we chat over drinks at one of his latest ventures, The Medicine Bar in Islington, it’s clear to see that a certain benevolence and charming affability has mellowed this once power-hungry capitalist.

Indeed, Webb now seems to have totally eschewed the aggressive, alpha-male approach to business, preferring instead a more humanitarian manner in his entrepreneurial endeavours.

‘I suppose I would call myself a social entrepreneur these days,’ he concedes. ‘I decided a few years ago that I should be giving something back – to be a player in society, rather than just being selfishly motivated.’

This is not rhetoric. His latest company, People’s Pubs, is the first UK pub venture to give all its profits away to good causes. ‘It occurred to me that rather than giving a lump sum to a charity, I should invest in a venture that would generate a return for good causes year after year.’

Since it launched last May in Brighton, People’s Pubs has donated £50,000 to charities benefiting the local community and is making a 33 per cent return on the funds he invested.

Building society background

Born in 1964 in Westminster Hospital and educated at Queen Elizabeth’s grammar school in Blackburn, Lancashire, Webb says his upbringing was not particularly entrepreneurial. ‘My father is a very good manager and became a key figure at the Woolwich building society in the 1970s, which perhaps gave me an acute awareness of money early on,’ he muses. ‘But my entrepreneurial drive originated from my basic desire as a kid to earn a lot of money when I grew up!’

This first manifested itself at Brighton Business School, where he started running events at nightclubs alongside his first year studies. ‘I effectively paid for myself to go to college, which was pretty unusual in those days. And it meant I learnt the realities of promotion and marketing when I was just 19.’

By the time Webb left with a degree in business studies, he was running four successful nights a week as a club promoter and went on to run his own club night for a time.

Failure comes knocking

Although he proceeded to work for the likes of Ernst & Julio Gallo and IBM, Webb always had the urge to go it alone. His first venture was a design company, founded with business partner Simon Kirbie, but it went bust within three years.

’We made all the classic mistakes,’ admits Webb, ‘confusing profit with turnover and drawing too much out. We were in our early 20s, so as soon as there was money in the bank we spent it, buying new cars and brick-like mobile phones. Flashing the cash around meant it soon ran out.

’In hindsight though, it was a hugely valuable experience. Failure teaches you so much. I’d say 70 per cent of what I learnt at business school wasn’t useful, though the other 30 per cent – about balance sheets, profit and loss statements and the like – was absolutely key.

‘If my first company hadn’t failed, I don’t think I would have been as successful as I have. There’s a certain levelling that happens when you fail, having to face that reality, telling your clients, friends and family – it makes you more responsible next time round. Once you’ve tasted failure, you never want to again.’

Sun shines on C-Side

Webb went on to launch bar chain C-Side in 1993 with a budget of just £5,000. ‘We practically begged, borrowed and stole to get that company off the ground,’ he remembers. ‘For the refit of our first bar site we did all the work ourselves, paying for it through a combination of part-time jobs, DJ’ing and credit cards.’ Luckily, the hard work paid off and the venue’s popularity led to regional expansion. In 1998, C-Side was listed in the Sunday Times Fast Track 100 as one the fastest-growing UK companies. By 2001, C-Side’s turnover had hit £20 million, profits were £2.3 million and it had 28 venues.

Webb sold the business to venture capitalist Foreign & Colonial Ventures, now Graphite Capital, for £15 million, which was the ultimate realisation of his childhood dream. ‘I’ve cashed in my chips and got the big payout from the business I built, so I can relax a little now and take risks with new challenges like I did in the early days.’

Risky business

Webb is currently taking part in Channel 4’s show Risking it all, due to hit our TV screens this September, in which he will guide a range of start-up businesses through their difficult first year.

‘I wanted to take part because I can relate to the title of the show, having personally put everything on the line during C-Side’s early years. I kept taking increasingly bigger risks, one in particularly being the £750,000 cash acquisition of a competitor, which could have easily backfired and put us out of business. During that time it really felt like I was in a Vegas casino, constantly betting big even though it could go wrong at any time. It’s not a business strategy I would recommend, but talking to these new business owners over the last six months’ filming brings it all back.’

Though his TV contract prohibits him from funding any of the ventures he advises, Webb says he’s always on the lookout for new investment projects. ‘There’s something naturally cyclical about your evolution as an entrepreneur – planning a business, making it a success, selling it on, starting something else. Each time you begin again you’re wiser than before.’

Commercial kaleidoscope

Webb’s other previous interests include founding, and then selling, Brighton radio station Surf 107, now Juice 107. His current ventures include the recently launched Dekoart, a web-based fine art digital printing company, and another pub company, Medicine Group, which has sites in Islington and the ever-fashionable Shoreditch in London. Next on the horizon is the launch of his French chateau-based country sports centre, offering diversions such as quad biking, clay pigeon shooting and horse riding.

Controversially, even with so many balls in the air, he’s adamant about staying hands-on in all his companies. ‘Running a business is not just a theoretical exercise, you need to live and breathe it, having total comprehension of every aspect. I hire managers when I absolutely have to, but I’m still involved day-to-day in all my businesses. We’re doing a bar refit at the moment and I’ve chosen all the paint colours, supervised the work and so on.’

With this level of commitment, it comes as no surprise to learn that Webb feels he’s sacrificed certain elements of his personal life in order to be a serial entrepreneur. Characteristically though, he’s making up for this fast – though unmarried, his first child is on the way, an impending event which he says is changing his perspective. ‘Working until 4am won’t be too conducive to being a father so I’m trying to take a step back. But it’s not quite working yet – I think I’m busier now than ever.’