The Entrepreneur Masterclass: Debbie Wosskow’s Blueprint For Success The Wobbly Middle podcast

The Entrepreneur Masterclass: Debbie Wosskow’s Blueprint for Success

1M ago 31:50

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Notebooks at the ready—this is a masterclass in taking ideas to thriving ventures from one of the UK’s most dynamic businesswomen. Debbie Wosskow OBE has built, scaled, and sold multimillion-pound businesses, including Love Home Swap, and now leads the charge for female founded businesses with the £250 million Invest in Women Taskforce and her new venture The Better Menopause.

In this candid conversation, Debbie shares the lessons learned from decades of experience: the sunlit uplands as well as the darkness. With a different business for every decade of her life, Debbie’s playbook is packed with insights to inspire your next move.

(00:00) - The Wobbly Middle S1 E7 Debbie Wosskow
(02:11) - Debbie's Early Career and Success
(05:07) - Personal Reinvention and Challenges
(15:19) - Building and Leading Female-Focused Businesses
(24:46) - Navigating Uncertainty and Personal Growth

For additional insights, read The Wobbly Middle on Substack. You can also find us on LinkedIn, Instagram and Facebook @thewobblymiddle.

If you are in the wobbly middle of your career, please share your story with us via our socials or email us at thewobblymiddle@gmail.com. We'd love to hear what’s on your mind - and if you're out the other side, please let us know how you got there!

About the hosts:
Susannah de Jager has just moved to Abu Dhabi. She is podcasting, consulting to start-ups and occasionally advising on scale-up capital having left her role as CEO of a boutique asset manager and asked "what next?”. In the last five years she has forged a new path following her passions and interests. This podcast is for her and for all those like her.

Patsy Day is a lawyer on a break. As an intellectual property specialist, she has worked on everything from anti-counterfeiting to publishing and from London to Ho Chi Minh City and back again. Patsy lives in Oxford and is currently immersed in podcasts producing SafeHouse Amsterdam (out 2025) and co-hosting, The Wobbly Middle.

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