Debbie Wosskow OBE on scaling a tech business, hiring in a hurry and diversity

Debbie Wosskow

If you’re involved in the UK technology industry in some shape or form, the likelihood is that you’ve already heard about Debbie Wosskow OBE.

For the benefit of those who haven’t, Wosskow can be best described as an innovator, founder, investor, board adviser, ardent supporter of the sharing economy, and a technology entrepreneur with a proven track record.

Focused on supporting female entrepreneurship and on a mission to make the UK a great place to be a working woman, Wosskow announced the creation of AllBright – a support network and funding platform for female founders – in October 2016, but she also set up and sold a series of successful businesses prior to that.

An Oxford graduate and former consultant at Oliver Wyman, Wosskow started her fruitful entrepreneurial journey in the world of public relations, setting up Mantra PR in 2000 and selling it to the Loewy Group – itself acquired in 2011 by Writtle Holdings – seven years later. She then went on to co-found Maidthron Partners, an advisory and investment firm focused on the creative industries.

“I think the driver for me was that I always wanted to run businesses because I’m from a very entrepreneurial family where everyone has their own business. I didn’t really have any context of people going to work, to do a job.”

“Mantra, for me, was an amazing first business. I was 25 when I set it up and it taught me a lot about the basics. When you run a professional services firm you learn a lot of hard lessons about managing a P&L, cash flow and people,” she told UKTN during a recent interview.

Despite working with clients in the technology space while at Mantra, it wasn’t until 2011 that Wosskow decided to fully dip her toe in the tech industry. She founded LoveHomeSwap – credited with being the world’s biggest exchange club for people looking to rent their property to other holidaymakers – after watching ‘The Holiday’, a relatively successful rom-com featuring Kate Winslet and Cameron Diaz. During the six and a half years that she was at the helm of the business, Wosskow raised just over $4m from investors including MMC Ventures.

Her previous business experience, she added, taught her invaluable storytelling techniques, which would come in handy during investment pitches, but what was perhaps most integral to the business’ success was the fact that she’d created a company which served her own needs. “I was LoveHomeSwap’s natural consumer and I think that really helped when it came to building the brand and the business.”

Wosskow eventually sold the business for a reported $53m to existing backer Wyndham Group, and her younger brother Ben stayed on as the CEO.

Execution, execution, execution

Looking back at her career, Wosskow says business success is about fully understanding the financials.

“It’s all about execution. I’m a very granular CEO and I think that’s one of my core strengths.”

In terms of challenges, she said the biggest issue she’d faced throughout her career is finding the right talent at the right time.

“You are only as good as your team and hiring is really hard. I’ve been doing it a long time and I still get it wrong. Hiring in a hurry is always a nightmare and things get even far more complicated when you’re trying to raise investment.”

“If you are trying to raise a round of capital, you tend to go through this ‘schizophrenic’ period of time where you don’t have enough money. After you’ve raised the cash, and you’ve sold a series of numbers to investors, you then need to hit those milestones and hiring needs to happen. This’ll never change,” Wosskow acknowledged.

Both as an entrepreneur and angel investor, Wosskow said the biggest piece of advice she can give fellow business people looking to raise investment is that it will always take longer than they expect – and it doesn’t get easier even if you have a great track record.

“The more experience you have, the more you think about raising from the right investors, at the right valuation and at the right time. It takes time,” she added.

Fundraising, she went on to note, is all about knowing your numbers. “People need to be very, very on top of how their business is performing and how it will perform in the future. Some entrepreneurs are very good at selling the dream to an investor, but I’m far more concerned about underpinning how the business will work.”

The business narrative typically notes entrepreneurs should start thinking about an exit from the onset, and Wosskow agrees, noting she tends to work in five year cycles.

Women in business

In an age where most of the cheques are signed by men and most of the funding typically goes to males, Wosskow believes there are certain things women in business should be aware of, address and change.

“I think, as a woman, you have to learn some lessons about not worrying about being liked. In particular, I do a whole speech about girls developing thicker skin.”

Like many of her contemporaries, Wosskow knows all to well that women are yet to achieve a place ‘at the table’. “We need to change the conversation. Diversity is good. Diversity produces better results.”

Wosskow admits that what she and her co-founder, ex Hearst CEO Anna Jones, are trying to do with AllBright is “very ambitious”, but fights against the perception that it is an ‘anti-male’ initiative, noting just how many “enlightened men”– many of whom are investors – have embarked on this journey with them.

Will AllBright be Wosskow’s last business, I ask.

“I don’t know. This one is different because I feel so strongly about the combination of profit and purpose and its personal to both Anna and I, but I what I would say is that I am exactly where I want to be with my fourth business.”