Debbie Wosskow is the founder and CEO of home-exchange service Love Home Swap. Since its launch in 2011, it has secured £7.5 million from Wyndham Worldwide and acquired rival outfits 1stHomeExchange and Home for Exchange. It was itself acquired by Wyndham in July. Wosskow also runs AllBright, a female-focused investment fund, and LifeStyler, an app for booking lifestyle experts. She previously co-founded PR company Mantra and investment firm Maidthorn Partners, and served as the founding chair of Sharing Economy UK. Here's what she's learned along the way.
Draw on lessons from childhood: "Coming from a Jewish immigrant culture, I grew up around people who started their own businesses. The talk around the dinner table as a kid was about business. In that sense, I've always been business-minded."
Non-business degrees add value too: "I did philosophy and theology at Oxford. The things I took from that were not necessarily the content - I don't spend an awful lot of time these days thinking about Hegel's dialectic - but the practical skills it teaches you. First is how to read very quickly and digest relevant information. Second is the tutorial system, which teaches you how to argue a case and to be a self-starter. I got a lot out of being there."
It's easier to start young: "Startups are really hard for the founder because you don't earn any money for years. It's not for the faint-hearted. So my whole mantra of 'What's the worst that can happen?' is very applicable at 25 years old, but it's harder to do that at age 40 when you've got a mortgage and two children."
The most successful entrepreneurs have particular qualities: "I call them the Three Gs. Graft - there's no magic to this, you have to work really hard. Grace - things happen and tempers flare, and you've got to look for people who are gracious enough to inspire teams but also able to get shit done. And Grit - because you can have days and weeks and months when things aren't going right. When investments I've made haven't worked out, it's generally because the entrepreneur hasn't had one of those, grit being the main thing."
1974: Born in Sheffield, South Yorkshire
1989: Won a Young Enterprise award
1995: Graduated from the University of Oxford
1995: Joined management consultants Oliver Wyman
1999: Co-founded Mantra PR
2008: Co-founded investment firm Maidthorn Partners
2011: Founded Love Home Swap
2015: Became chair of Sharing Economy UK
2016: Launched female-founder VC fund AllBright
2017: Co-founded personal styling app LifeStyler; Love Home Swap acquired by hotel giant RCI, part of Wyndham Worldwide
Hiring takes time: "Hiring people is really hard. Even when you have experience it's still very easy to make big and expensive mistakes from a hiring perspective, so my advice would be to always take your time. Whenever you're rushing a hire and you think, 'That's fine, they're good enough,' they're not the right hire for your company."
Find an investor who believes in you: "As an entrepreneur, I'm looking for an investor who has my back. That doesn't mean that they're endlessly patient, but it does mean they want me to win."
Good ideas tick three boxes: "With potential business opportunities, the three tests for me are: if it keeps you awake at night; if you can see from a business perspective that it would work on Excel; and if you feel you can understand the customer."
Use your own experience: "The inspiration for Love Home Swap came during a disastrous holiday when my children were young. On the flight back I watched the movie The Holiday, which is the ultimate home-swap movie. It resonated because my home in London was empty while we were away, and we spent lots of money on the holiday but I just wanted to be home."
Connect with other founders: "It's a lonely life as an entrepreneur, especially when you're young. When I was 25, I was employing people, winning business and dealing with property, and not many of my friends were doing the same thing. I have a close-knit network of other female founders, and to me that feels like a safe space."
The best partners have different skills: "Anna [Jones, co-founder of AllBright and executive chairman of LifeStyler] has a very different background. She went from being a graduate trainee at magazine publisher Hearst to being the boss by the time she was 37, so she's a fantastic operator. But I have had these small businesses that go from being an idea to a thing and then I sell them. In a sense, we're able to divide and conquer."
Don't shy away from the spotlight: "If you are a platform entrepreneur where you're selling a product, it's helpful for people to know who you are."
You need a thick skin: "If I've achieved anything over the past 20 years, it's that I've developed the hide of a rhino. If somebody writes something you don't love about you or your business, or when you're pitching for investment and you get a 'no', which is often, no matter how successful you are - I took that personally when I was in my twenties. Now, I don't take it personally at all."
Exercise is vital time to yourself: "I do something every day of the week apart from Sunday. If I'm travelling, I fire up [training app] Insanity on my iPad and do it in the hotel room with bottles of wine as weights."
This article was originally published by WIRED UK
