S21 Ep4: Graft, grace & grit with Debbie Wosskow OBE, entrepreneur, investor, author & co-founder of All Bright

What would you say to your 21 year old self? What advice and wisdom would you share? In this micro episode, we hear from Anya Hindmarch CBE, accessories designer, design and arts advocate, sustainability campaigner and Sunday Times bestselling author.  as she gives us a glimpse into the world through her eyes with an intimate letter written to her younger self. With an unique ability to make the ordinary, extraordinary, Anya’s letter is a love note to self, one that encourages and supports, advises and guides. This is your micro shot of inspiration and an episode that brings to life the transformative power of a simple letter.

What drives someone born into one of the UK’s most prominent aristocratic families to dedicate their life to prison reform, particularly advocating for the needs of women behind bars? In this episode, Holly speaks with the remarkable Lady Edwina Grosvenor, whose background might lead you to expect a life of privilege and tradition—but her story is anything but conventional. Edwina shares how, “From a really young age, I felt that injustice of the luck of birth,” an early realisation that sparked her commitment to the most marginalised members of society. From the impact of privilege on her perspectives to her work in addressing the systemic injustices faced by incarcerated women—like the lack of access to basic necessities—Edwina shares a rare, firsthand view of the hidden world of prisons. She dives into the complex relationship between domestic violence and incarceration rates, and why trauma-informed care is essential for breaking cycles of recidivism. She challenges us all: “Do we want our prisons to be warehouses for the incorrigible or greenhouses for the redeemable?” Her vision for a more compassionate justice system is clear: “Should we be helping people to lead a better life or should we be actively preventing it?” Listen now for a conversation that will open your eyes, challenge your assumptions, and inspire you to consider how empathy can drive real change. Join us in exploring the hidden world of prisons and the transformative power of hope. Win an Independent Ad Break on Conversations of Inspiration: Are you a founder with a story to share? Enter for a chance to win your own ad break on this podcast. This opportunity is brought to you in partnership with Dell Technologies, supporting startups with expert advice and scalable solutions. Exclusive Dell discount for Conversations of Inspiration listeners: Save up to 20% through Dell Exclusive Offers by using your email and the exclusive Holly & Co password: ‘HCO’. Trigger warning: This episode includes discussions about the deaths of babies, which may be distressing for some listeners. If you need to, please skip from 26 to 28 minutes. Take care while listening.

In this micro-episode, Holly revisits the extraordinary letter Sophie Morgan—TV presenter, author, and disability activist—wrote to her younger self. Sophie shares her powerful story of resilience after a life-altering car accident at 18 left her paralysed, yet propelled her towards a new, vibrant path. Through her letter, she reminds us that the tenacity and strength often labeled as "difficult" are the very qualities that help us overcome life’s toughest moments. This episode will leave you feeling empowered and inspired to embrace your inner strength, no matter the challenges you face. You’ll take away insights into: The power of resilience: Learn how Sophie turned adversity into triumph, showing that even life’s hardest moments can lead to a bright and colourful future. Embracing your true self: Discover why the very traits that others might see as difficult can become your greatest assets. A new perspective on hardship: Sophie’s wisdom will inspire you to find light in dark times and to keep moving forward, step by step. This episode is your micro-shot of inspiration, offering a heartfelt reminder that no matter where you are in life, you have everything you need within you to get through it all.

Imagine turning down a dream job, facing a mountain of debt, and surviving a life-or-death experience—only to emerge with a mission that’s transforming the world of giving. In this episode of Conversations of Inspiration, Matt Pohlson, co-founder of Omaze—a platform that offers life-changing experiences and prizes while raising funds for charitable causes—shares his remarkable journey. It’s packed with insights for anyone looking to make a difference. What you’ll learn: Turn fear into fuel – Matt reveals how he overcame $200,000 in debt and turned down a major job offer, staying true to his mission even when the challenges felt insurmountable. Build trust through vulnerability – Find out how embracing honesty and openness can forge deeper connections, whether in business or in life. Combine profit with purpose – Discover how Omaze has raised over £60 million for charities by harnessing the power of storytelling. Matt’s story is a powerful reminder that our toughest moments can become our greatest sources of strength. Tune in to see how these lessons could shape your own journey. Win an Independent Ad Break on Conversations of Inspiration: Are you a founder with a story to share? Enter for a chance to win your own ad break on this podcast. This opportunity is brought to you in partnership with Dell Technologies, supporting startups with expert advice and scalable solutions. Exclusive Dell discount for Conversations of Inspiration listeners: Save up to 20% through Dell Exclusive Offers by using your email and the exclusive Holly & Co password: ‘HCO’.

Dive into this inspiring micro episode of Letters to My Younger Self with Richard Reed CBE, co-founder of Innocent and Jam Jar Investments. In this heartfelt letter to his younger self, Richard shares invaluable life lessons that offer profound insights for anyone navigating their own journey. Listeners will gain: Empathy and Connection: Discover how Richard’s reflections on friendship and vulnerability resonate with your own experiences, fostering a deeper understanding of life’s challenges. Life Lessons: Gain practical wisdom about embracing sadness as an asset, learning to navigate fear-based thinking, and recognizing the importance of authenticity in building meaningful relationships. Inspiration for Growth: Feel motivated to reflect on your own journey and connect the dots of your past, realizing that every experience contributes to the person you are today. Join us to uncover the transformative power of self-reflection through Richard's heartfelt words. This episode promises to uplift and inspire, reminding you that you are not alone on this journey—your story matters.

Meet Patrick and Karen O’Flaherty, the dynamic husband and wife duo behind Pip Organic, a pioneering force in the organic food and drink industry. Their story began in the bustling heart of London, where their shared passion for health, sustainability, and community blossomed into a visionary business idea. United by their commitment to creating wholesome, organic products, Patrick and Karen embarked on a journey to transform the way people consume food and beverages. In this episode, Patrick and Karen reveal the intricacies of their entrepreneurial journey sharing the complexities of being an organic business and managing a sustainable supply chain all whilst ensuring that Pip Organic remains synonymous with purity and simplicity. But it’s not just a story about business, Patrick and Karen’s journey is also testament to the remarkable power of a family-run enterprise and of how they have woven their personal values into the fabric of their brand. Win an Independent Ad Break on Conversations of Inspiration: Are you a founder with a story to tell? Enter for a chance to win your own ad break on this podcast. This competition is delivered in partnership with Dell Technologies, supporting startups with expert advice and scalable solutions. Exclusive Dell discount code for Conversations of Inspiration listeners: You can save up to 20% off via Dell Exclusive Offers with your email and your exclusive Holly & Co password ‘HCO’.

In this deeply reflective micro-episode, Holly revisits Wilfred Emmanuel-Jones’ powerful letter to his younger self. Wilfred, a businessman, farmer, and founder of The Black Farmer, has always forged his own path, and his letter serves as a heartfelt reminder of the timeless wisdom we often overlook as we grow older. Inspired by Baz Luhrmann’s ‘Wear Sunscreen’, Holly delves into Wilfred’s words, which highlight the importance of holding onto childlike curiosity, passion, and adventure, no matter our age. His letter is a rallying cry to live fully and fearlessly, especially in the face of adversity. This episode is your micro-shot of inspiration—an invitation to rediscover the adventurous spirit we had as children, and a testament to the transformative power of a simple letter to guide us through life’s toughest moments.

What does it really take to build a legacy of success while lifting others up along the way?  In this episode, Holly speaks with Debbie Wosskow OBE, the powerhouse entrepreneur, investor, and author behind multiple thriving businesses. From her entrepreneurial roots, Debbie grew up understanding the value of hard work and resilience - traits that have fueled her remarkable journey from founding Mantra, Love Home Swap and AllBright to empowering thousands of women across the globe. Now, at 50, Debbie reflects on how she’s become the fullest version of herself—balancing entrepreneurship, life and her role as a champion for investing in female-founded businesses.  Debbie’s journey is a powerful reminder of the strength and tenacity of women in business. Her insights on grit, grace, and graft will inspire you to recognise your worth and pursue your dreams with confidence. Whether you’re an entrepreneur, a professional, or someone seeking personal growth, this episode of Conversations Of Inspiration is packed with wisdom and encouragement. Win an Independent Ad Break on Conversations of Inspiration: Are you a founder with a story to tell? Enter for a chance to win your own ad break on this podcast. This competition is delivered in partnership with Dell Technologies, supporting startups with expert advice and scalable solutions.  Exclusive Dell discount code for Conversations of Inspiration listeners: You can save up to 20% off via Dell Exclusive Offers with your email and your exclusive Holly & Co password ‘HCO’.

In this inspiring micro-episode, Holly revisits the heartfelt letter written by Joe Wicks, the nation’s favourite fitness coach, to his younger self. Known for his infectious energy and passion for helping others, Joe reflects on the challenges and self-doubt he faced on his journey to becoming a "10-year overnight success." His letter offers a rare glimpse into the personal moments and decisions that shaped his extraordinary rise to fame. This episode will inspire anyone who has ever felt lost or unsure about their path in life. Joe’s words remind us that: Success takes time: Learn how perseverance and consistent effort are the keys to achieving big dreams, even when the journey feels overwhelming. Overcoming self-doubt: Joe’s letter shows how he navigated feelings of uncertainty and turned them into fuel for his personal growth and success. Embracing opportunity: Discover how preparation and seizing the right moment can create life-changing opportunities. This episode is your micro-shot of inspiration—an uplifting reminder that no matter how long your journey feels, you are capable of turning your dreams into reality.

Paul Hargreaves, the visionary founder behind Cotswold Fayre, a speciality food wholesaler, and Flourish, a 9,000 ft food hall, restaurant and home and lifestyle store is a journey is one of remarkable resilience and purpose-driven leadership.  With an unwavering commitment to his values,  Paul shares with Holly the profound impact of a life changing trip to Kenya that shifted his perspective, igniting a deeper commitment to creating a business that prioritises people and the planet alongside profit. A passionate ambassador of the B Corp movement, Paul champions the fourth bottom line - the belief that it is only through personal change and with empathy and authenticity, that we can become compassionate leaders and drive both personal fulfilment along with business success. So whether you are an entrepreneur, business leader or someone passionate about making a positive impact through business, this conversation, from one of the industry's leading voices, is one packed full of wisdom and inspiration on how you too can make a meaningful difference. This heartfelt conversation offers a wealth of wisdom for entrepreneurs and leaders looking to infuse their ventures with purpose and humanity. Plus, for weekly inspiration, creative ideas and more from brilliant small businesses, sign up to Holly's emails. Or for more insights into building a purpose-driven business, subscribe to Holly’s monthly newsletters. You'll also get exclusive offers and 'ungoogleable' business advice delivered straight to your inbox. Win an Independent Ad Break on Conversations of Inspiration: Are you a founder with a story to tell? Enter for a chance to win your own ad break on this podcast. This competition is delivered in partnership with Dell Technologies, supporting startups with expert advice and scalable solutions.  Exclusive Dell discount code for Conversations of Inspiration listeners: You can save up to 20% off via Dell Exclusive Offers with your email and your exclusive Holly & Co password ‘HCO’.