Growing up in a powerful female-led family
Debbie Wosskow didn’t set out to become a serial entrepreneur. The path unfolded naturally.
Her first business, a scrunchie company launched at 15, won a Young Enterprise Award in the 1980s. Since then, she has built, sold, and exited multiple companies, including Love Home Swap, which Wyndham Worldwide acquired in 2017 for $53 million. Now, she invests in female-led ventures targeting midlife women, such as The Better Menopause, a company she co-founded with business partner Anna Jones and nutritional therapist Joanna Lyall.
The matriarchy that shaped her
Wosskow grew up surrounded by self-employed women. Her grandmother ran a chain of sweet shops and off-licences. Everyone in her family worked for themselves, and money was a common topic at the dinner table. By 25, starting a business didn’t feel like a risk—it felt like the obvious next step.
“If it’s normal to see everyone in your family going to work for themselves, you don’t think it’s a risky decision,” she explains. “At 25, it really isn’t.”
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That mindset led her to create Mantra, a marketing and PR agency, in her mid-20s. She ran it for eight years before selling to Loewy Group for a multi-million-pound sum in 2007. The experience taught her the fundamentals of business—profit and loss, cash flow, balance sheets—lessons she still uses today, despite studying Philosophy and Theology at Oxford.
“An agency is a great first business,” she says. “You’re always two account wins away from success and two losses away from trouble. I learned how to price work, build a team, and manage finances. That paranoia about cash flow has stayed with me 25 years later.”
She also discovered the importance of storytelling. Even now, she drafts press releases in her head before making decisions. “It helps you spend your time wisely,” she notes.
From necessity to $53 million
Wosskow’s next venture, Love Home Swap, emerged from necessity. As a single mother to two young children at the time, she says the business had to succeed. Inspired by the film The Holiday, the online home exchange network grew until Wyndham purchased it in 2017 for $53 million.
“Inspiration can come from anywhere,” she says. “But you still have to be really bloody-minded and work hard.”
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During this period, she advised the UK government on the sharing economy, wrote reports, and founded Sharing Economy UK, a trade body. That work taught her the value of having a platform. “You are a standout asset for your own business,” she says.
Lessons from the rear-view mirror
Wosskow’s career holds key lessons. The first: launch a product quickly. “If you’re not embarrassed by your first version, you’ve waited too long,” she says, quoting LinkedIn co-founder Reid Hoffman. She has built businesses around this idea, balancing customer acquisition costs with lifetime value.
Her most important relationship is with her business partner. “I met Anna Jones at a party I almost skipped,” she recalls. “Small moments can change everything.”
Wosskow received an OBE for services to business in 2016. She serves on the Mayor of London’s Business Advisory Board and was recently named a non-executive director for Channel 4. Her book, Believe. Build. Become.: How to Supercharge Your Career, co-written with Anna Jones, shares some of these insights.
