The leading US entrepreneur who made her fortune in lorries and insurance tells MAGGIE ROSEN a thing or two about risk and reward

First thing first: no one seems to know what the V stands for. Officially, it’s ‘silent’, which begs the question of why it’s there in the first place. Whatever the answer, V Cheryl Womack must be feeling pretty good. She’s just made $1.6 million (£806,351) by auctioning half her wine cellar, through Sotheby’s. But selling it wasn’t as much fun as putting it together.

As a woman who, aged 31, founded a group of independent lorry drivers (‘truckers’ in the US) and then made a fortune selling them insurance, she likes a project. ‘When I built my first cellar, I decided it should hold about 5,000 bottles,’ recalls Womack, now 57. ‘I had fewer than 100 but thought: what’s the point of a cellar that can only hold a handful of bottles?’ Womack began buying wine after being introduced to Napa by a San Francisco restaurateur. ‘I fell in love with Joseph Heitz’s wines and in 1979 bought six bottles of Martha’s Vineyard 1974 for about $27. ‘To me, at the time, that was a lot. I drank the last bottle in 1996 – it was still spectacular. I looked up the value and found it was worth $300 and considered whether I liked it better. Although the value had no bearing on my enjoyment, it made me stop and think about just drinking wine without giving any thought to its value.’ Womack says she’s applied a ‘test of time’ philosophy to every purchase, including the full complement of first growths she began buying en primeur in 1994, along with Pétrus, Le Pin and d’Yquem. ‘I ask myself: could I sell it and get out of it at least what I paid? In most instances, this method has served me surprisingly well.’ So much so that the only investments Womack has made more from are property and art. ‘Wine is a close third, with better results then the stock market or bonds,’ she says. A case in point was her investment in 1990 Champagne.

‘Before the millennium, I had the chance to buy 100 cases of Dom Pérignon, Cristal and Veuve Clicquot La Grande Dame,’ she says. ‘I was getting married, planning two receptions and wanted to have a pretty good party. I didn’t think I’d have trouble drinking them over time.’ Her investment was made all the sweeter as the prices have risen ‘ridiculously’. While those Champagnes, plus several cases of Krug Clos de Mesnil 1985 and 1989, were part of the recent Sotheby’s sale, Womack still has 10 cases of top fizz for a rainy day. ‘I don’t believe you should own wine you wouldn’t get excited to sit down and drink or share,’ she says. ‘So my strategy was to buy a little, then drink a little. Eventually I ended up buying a lot.’ Womack says she became a ‘sponge’, reading magazines like Decanter and Wine Spectator, following critics’ ratings and points, but also tasting for herself. These days, Italian and Australian bottles are her everyday wines, as she no longer drinks much California wine aside from Cakebread Chardonnay. ‘I also like Oregon Pinot Noir, she says, ‘especially when dining out.’

Another thing that has served her well is her ability to spot an opportunity, which led to the decision she made 26 years ago to quit a dead-end job and go it alone. ‘I think like a man,’ she says. ‘I make decisions very quickly and don’t regret them. If I make a mistake, I analyse it and move on. I don’t sit around worrying – I just make sure I don’t do it again.’ Most of all, Womack relishes the chase – and a bargain. ‘I found some Penfolds Grange in stateowned liquor stores in areas where customers weren’t familiar with the wine. There’s nothing more exciting than finding a great vintage still for sale for the same amount it was initially priced at.’ On the other hand, she feels Opus One is over-hyped and overpriced. ‘Don’t get me wrong,’ she says, ‘it’s a good wine. But there are so many better choices for the same amount or less.’ Aside from her first bottle of Screaming Eagle (see box, left), Womack has rarely paid more than $300 for a single bottle. That’s because, just as she loves wine, she’s hard-pressed to take the business out if it. ‘I’ve bought wine from the heart but sometimes I have to walk away,’ she says. ‘It’s one of the reasons I’ve stayed away from Burgundy – though I love it, I’ve never been sure I could resell it.’ And now is the time to reap the rewards of the risks she has taken. ‘I’ve spent most of my working life building companies, then realised my worth was tied up in building more,’ she says. ‘Suddenly I reached an age where I said: “What is more? Is it more stuff, or how I spend my life? Do I have time to enjoy a glass of wine, or will I be interrupted by a phone call?”’ That said, since selling her companies in 2002 for $100m, she hasn’t slowed down. Now she plans to put the revenue from the wine auction to work. ‘I’ll reinvest it – but not in wine,’ she jokes, saying she’s looking for something riskier. ‘There are lots of real estate opportunities in the US… maybe I’ll buy some property…’

Written by Maggie Rosen