No Handbag, just the height of web fashion

Dropped names litter Nancy Cruickshank's conversation like confetti at a society wedding. The good and the great of the rapidly converging world of publishing – online, newspaper, magazine, masthead television, and, er, knowledge video platform – march along in loose formation amid the lava flow of words issuing from her mouth.

From Stephen Quinn, the publisher of Vogue, now better known as Mr Kimberly Quinn; to Nicholas Coleridge, the managing director of Vogue publisher Condé Nast; to Elisabeth Murdoch; to Aidan Barclay, representative on earth to the Barclay twins, owners of the Telegraph Group; to Andrew Neil; to serial entrepreneur David Tabizel, a fellow who, Cruickshank intones breathlessly, has an IQ of 200 (pity he's not smart enough to stop her going round telling everyone) – she has worked with, or mostly for, them all.

Cruickshank, bouncy, blonde, nearing 40, is an internet entrepreneur – one who isn't displeased by the connotations of being an outsider. She managed to survive the crash of the first wave of dot coms (techie vernacular: "Internet 1.0") and even came out slightly ahead. But she plays an interactive, insider game, as the gleeful recitation of her contacts book might indicate, and made a tidy chunk of capital in the second wave (oh, all right – "Internet 2.0") with the sale of the Handbag Publishing Group to the National Magazine Company, part of the Hearst group.

Cruickshank is now chief executive of the hideously named VideoJug, which we'll come to later. Handbag, a muscular online celebration of girliness, basically accounted for her career from 2001 to the end of last year. It's her defining achievement and her flagship deal.

So let's start with the bleedin' obvious: how much did she sell it for?

For the first time, Cruickshank hesitates, and looks round the small anteroom just off VideoJug's cramped, silicone-sweatshop premises on Shaftesbury Avenue in the West End of London. The sound of the 30-odd employees outside, dutifully clicking at their machines, drifts into the room (as in many an internet business, there's an air of battery-farm conformity in the office). Well, it's basically confidential and she can't really say.

But she claimed a big stake when she negotiated the change of ownership from Hollinger, the former owner of the Telegraph newspapers, and Boots, the high-street chemists chain, to the Barclay brothers. What she can tell me is that when Handbag was sold to Hearst 18 months later, she made a huge turn on the deal. Cruickshank insists on playing a parlour game ("Ten times?" "More." "Twenty?" "More." "Fifty?" "Not much less.")

Perhaps Cruickshank is so coy because she has a couple of employees sitting in on the interview. Maybe it's just she has that British thing about money and trade being vulgar. She doesn't seem to realise that doing a really smart deal is actually endearing – although not, one imagines, to Richard Baker and his team at Boots. ("There was a lot of change going on there at the time of the deal. I think the Boots team were mainly concerned that Tesco wasn't going to eat their lunch," she smiles.)

Fortunately, our irritating parlour game turns out to be an irrelevance. After the interview, Cruickshank mails me a voluminous, seven-page CV, which proclaims that the Handbag deal was done for £22m. Given the Barclay brothers' determination to own and control things, that puts Cruickshank's stake well south of 25 per cent. Still, she'll probably have made £4m or so.

Good for her. Moreover, with two daughters under six, she still wants to work – hard, too, one suspects. And she's leading a business that's at the cutting edge of the knowledge economy –one which provides substantial employment. In my book, although Cruickshank needs presentation training like a whale needs plankton, that makes her one of the good guys.

Now, just as the rest of the world is imploding, she's on the acquisition trail and is doing due diligence on an American technology company to bolster her fast-growing business. VideoJug started life with some £15m, raised from Master of the Universe Tabizel and other high net-worth individuals.

The business is a "big social knowledge network", says Cruickshank. "It's the biggest short-form social knowledge library on the internet, I believe. We create the knowledge store, and we have interactive tools and community functions."

Cruickshank says that "about 60 per cent of the traffic comes in from natural search". The company also performs that little techie trick known as "search engine optimisation", so that if you want to know how to make the perfect teriyaki chicken, open a bottle of champagne without spilling any, or build your own cold-fusion nuclear reactor etc, it should come out pretty near the top of your Google search.

VideoJug is a beneficiary of the user confidence that has seen a second generation of internet companies flourish. The site syndicates its content to MSN, MySpace, YouTube and the like. Cruickshank makes a strong case as to why online video attracts advertising. Basically, you stare at the screen for a bit as the thing you're downloading gets going and later signs itself off. In today's world, the guarantee of just a few seconds of consumers' attention is enough to attract substantial advertising spend, apparently. Although there are plans to raise more money and acquire businesses, VideoJug itself should be profitable in the first quarter of next year, according to current projections.

All in all, Cruickshank has come a long way from the 11-year-old girl who cried for three weeks when her parents sent her to boarding school and moved to Hong Kong. That seems less of an issue for her these days than the fact that she failed to take up an offer to go to Christ Church, Oxford. ("My dad was a self-made man ... I just didn't think I'd fit in.") She suffers slightly from Alan Yentob syndrome (both insist with unnecessary vehemence that opting for Leeds over Oxford was a really good idea).

After leaving Leeds with a degree in history, Cruickshank spent a bit of Daddy's money travelling the world, then settled into a succession of magazine, advertising and media sales jobs. Notable points included The World of Interiors magazine (published by Condé Nast), British Sky Broadcasting, where she headed [.tv], a ludicrously titled technology channel, and a property sales portal called smove.com (it doesn't get any better, does it?). Then came Handbag, and now this.

So where next for the tech economy's ultimate insider? Her husband is also a techie, and in the medium term they are thinking of moving to the States, where half the staff of VideoJug are based. But ultimately Cruickshank is going to go wherever her business sense takes her. She's done one big transaction, and now she's hooked: "What gives me most pleasure? Nailing a deal. Once a saleswoman, always a saleswoman."