The business idea inspired by Hollywood

Annabel Denham
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Annabel Palmer talks to Debbie Wosskow, the serial entrepreneur whose third venture is planning to change the way you holiday

THE TRENDY Shoreditch offices, home to Debbie Wosskow’s latest venture Love Home Swap, sit slightly uncomfortably with the glamorous entrepreneur who knows her way around a power dress. Despite setting up her first company at 25, Wosskow, now 39, didn’t come up with the idea for what she now describes as her “baby” until three years ago. It’s an online home swap holiday company that, after just two years, has 40,000 properties on its books.

Wosskow comes from a family of entrepreneurs, and says it’s in her blood. “I have the defining characteristics of an entrepreneur,” she says confidently. “I’m focused, dogged, and have a short attention span.” Her grandparents ran newsagents and off licences, her mother runs her own business, and her younger brother is chief marketing officer at Love Home Swap. As such, she is diffident of how young she was when she created her first company – an agency business doing online marketing and acquisition for internet companies. “When you’re that age, you’ve got nothing to lose,” she shrugs. The business – Mantra – was sold in 2007.

The idea for Love Home Swap came from a combination of watching The Holiday – the Cameron Diaz/Jude Law outing in which a week-long home swap leads to life-long romance – and personal experience. “I always loved to travel, usually staying in boutique hotels. But staying in those places with kids is a nightmare.” Her own research led to the discovery of what she believed was a gap in the market. Airbnb, her San Francisco-based market competitor, had just been created, and there was opportunity for other early adopters. Wosskow believed the market was “ripe for innovation,” so she “invested in developing the concept of an online community from an idea to something that’s a big global business”.

I ask how her startup experiences have been different second time around, both on a personal level and in terms of the economic environment. Wosskow responds that she has directly felt the effects of the tax incentives for investing in small businesses – and the transformational effect of the government’s Enterprise Investment Scheme and Seed Enterprise Investment Scheme. She found it easier to access capital this time – for her first company she used a £3,000 bank loan and only after a year did she take on venture capital. These incentives for both investors and entrepreneurs didn’t exist back in the early 2000s, she says. “When I sold my first business, the Entrepreneurs’ Relief of 10 per cent on the first £10m of a lifetime profit (introduced in the March 2011 budget) didn’t exist. I paid 18 per cent and 28 per cent on the proceeds.”

This time around, Wosskow and her business partner invested the first £250,000 into the business. “It made a huge difference. We didn’t have to get involved with angels, or worry about having 18 cheques for £10,000 coming in.” Having deeper personal pockets made seeking investment later easier – it showed investors that she was putting her feet close to the fire. And she knew exactly who to go into business with. Her brother, Ben, was set to do an MBA, but Wosskow dissuaded him, told him she would salary him, and that his “steady, calm and analytical” skills would complement hers.

Love Home Swap has rapidly reached 40,000 homes. It recently acquired First Home Exchange – a French-Canadian website – to help build its inventory in France. The next phase of the business is to get more fundraising and acquire other sites and their inventories. “But fundraising is hard. It takes up a lot of time – always more than you think – and the European fundraising culture is frustrating. No-one can say ‘non’, so you often end up wasting a lot of time.”

Almost 82 per cent of her company’s members have never home swapped before, and 80 per cent of its inventory is unavailable elsewhere online. It may seem surprising that so many people are willing to put their fears about returning to a ransacked home aside and use her website. But “people are more open now. It’s the era of couch-surfing, and we’ve created a community – it feels like a club.” Perhaps it helps that the average age of a home-swapper through Love Home Swap is 46 (on AirBnB it’s 29), and the average value of the homes is £1.5m. The company makes its money in two ways. First is a membership subscription fee (ranging from £119 to £399). For non-members, the business model is “pure online dating: free to list; pay to message. But the business is very appealing to investors, because it’s a true marketplace company – not a build it now and in seven years it will monetise.”

While Wosskow says she’s been 100 per cent focused on Love Home Swap for the past two and a half years, she remains unemotional about businesses more generally. “I think this has really good legs – we had a board meeting this morning and we are on target – it’ll be properly scaled as a valuable community, and then we’ll sell it.” This is partly because of her self-confessed short attention span, but also because she has another interest – dating back to her years at Mantra. In 2009, she set up Maidthorn, an investment boutique, with an old friend. Through it they have invested in five early stage companies. She seems keen to go into private equity one day. “Well, from a tax perspective, it makes sense to invest in other businesses. I’d rather do that than give more money to my independent financial adviser. And it’s a useful discipline, it helps me understand more about making a company successful. Also, I like other entrepreneurs, and this gives me a perfect opportunity to meet them.”

Company Name: Love Home Swap

Job Title: Chief executive

Founded: 2010

Number of staff: 13

Age: 39

Born: Sheffield

Lives: Little Venice, London

Studied: Philosophy and Theology at New College, Oxford

Drinking: Grey Goose Vodka

Eating: Sushi

Reading: Bringing up the Bodies, by Hilary Mantel

Favourite Business Book: Built to Last, by Jim Collins

Talents: Boxing, standing on my head, and speed-reading

Motto: “Be the best you can be”

First ambition: To be an Olympic gymnast

Heroes: Tank Girl