KEY THEMES

• Learning through missteps and setbacks

• Redefining business culture

• Building trust and autonomy

• Turning frustration into bold action

Jeff Dewing shares his transformation from hands-on engineer to founder and leader of Cloud FM. Discover how a series of setbacks, experiments, and unconventional choices led him to redefine his career—and success—on his own terms.

KEY THEMES

• Breaking industry and gender stigmas

• Learning through personal struggle

• The power of small, repeated actions

• Building self-compassion as a founder

Vishal Narbheram spent years on construction sites before founding Onward Shift, confronting both his own mental health struggles and the industry’s deep-rooted stigma. This episode follows his gradual, sometimes messy journey from electrician to founder, and the lessons he learned about self-compassion and taking imperfect action.

KEY THEMES

• Navigating Imposter Syndrome and Self-Doubt

• Making Expertise Accessible

• Embracing Career Serendipity

• Finding Purpose in Teaching Others

  How does a motorcycle mechanic and software engineer become a leading voice for systems thinking? In this episode, Carolina Cunnington shares her candid journey from uncertainty and career change to redefining what it means to teach and lead.

KEY THEMES

• Responding to crisis with action

• Confronting educational inequality

• Building through collaboration and adaptation

• Motivation and resilience under uncertainty

Amid upheaval and inequality, Serena Siebel left the private sector to transform education for those with the least. This episode uncovers the events that propelled her shift—and the hard-won lessons behind her commitment to equity.

KEY THEMES

• Navigating identity after career disruption

• Building resilience through uncertainty

• Adapting leadership across sectors

• The slow process of entrepreneurial becoming

Resilience consultant and business leader Alison Charles shares how early ambitions, career setbacks, and life in the military shaped her approach to entrepreneurship, leadership, and organisational change. Hear how she navigated personal transition, overcame barriers, and built a business around helping others adapt.

KEY THEMES

• Finding confidence in male-dominated spaces

• Building community from need, not perfection

• The evolving role of mentorship and allies

• Experiencing and preventing burnout in tech

How does someone move from being “the only woman in the room” to building a thriving community for female product leaders? Becks Yelland joins Interwoven to share the motivations, missteps and meaning behind founding Female Product Lead.

KEY THEMES

• Navigating uncertainty as a young founder

• The power of collaboration and conversation

• Carrying forward skills from unexpected places

• Redefining success and purpose

Jack Sykes left behind the expected graduate path to build a venture that supports other founders. In this conversation, he reflects on uncertainty, reinvention, and the lessons learned as a young entrepreneur shaping his own journey.

KEY THEMES

• When conviction fuels reinvention

• Turning burnout into organisational change

• Navigating risk and uncertainty

• Merging creativity with environmental action

TV presenter and author Natalie Fée shares her unconventional leap from the media world to leading City to Sea. Discover what pushed her to abandon a successful career for an uncertain mission, and what she learned about resilience, reinvention, and making change when the path isn’t obvious.

KEY THEMES

• Personal loss shaping purpose

• Career reinvention through wellbeing

• Building support networks from scratch

• The vulnerability in starting over

How do life experience, loss, and deep care for others drive people to reinvent themselves? This episode traces the journeys of Lynn Smith, Gail Jones, and Maxine Simons, revealing how the Good Health at Work initiative took root—messy beginnings, real risks and all.

KEY THEMES

• Moving from theory to practice

• Turning frustration into opportunity

• Building through collaboration

• Redefining success as impact

What pushes two professionals to step off a stable career path and try building something of their own? Onome and Tulu share the candid story of how curiosity, frustration, and community shaped their journey into founding Recreates.

KEY THEMES

• Reinventing identity amid changing work cultures

• From salary-driven to purpose-driven careers

• The enduring power of human connections

• Adapting to new recruitment technologies

When seasoned IT recruiter Paul Vingerhoets found recruitment and workers changing after the pandemic, he didn’t just adapt his methods. He re-examined his purpose, his relationships with work, and what it means to build a meaningful career.

KEY THEMES

• The tension between security and freedom

• Limits of turning passion into business

• Self-doubt and the challenge of self-promotion

• Iterative, experiment-driven transitions

Nutritionist Julie Taplin opens up about the uncertainties and realisations that surfaced as she weighed stepping away from a secure career to pursue her own wellness business. Discover the fears, trade-offs and small acts of courage behind every founder’s journey to something new.

KEY THEMES

• Turning loss into meaningful action

• The uncertainty of being a founder

• Redefining personal success and identity

• Building community through authenticity

After losing his brother at 22, Toby Freeman left behind his former life to found the Robin Cancer Trust. In this episode, he shares how personal tragedy, uncertainty and community have shaped his unconventional path from bartender to charity leader.

KEY THEMES

• Redefining success through experimentation

• Letting go of perfectionism

• Building confidence as a freelancer

• Learning from setbacks and feedback

Medical writer Sarah Neilson shares how a career built on scientific research gradually evolved into founding her own business. Discover the mindset shifts, risks and discoveries that come with leaving a secure path to build something original and meaningful.

KEY THEMES

• Becoming a beginner again

• Learning through setbacks and adaptation

• Redefining success and identity

• Navigating uncertainty and risk

Life as a founder is rarely a straight line. In this episode, we meet Jamie Lumsden, Tom Steel, and Peter Disney, three people who left stability behind to build something new, discovering both challenge and fulfilment on uncharted paths.

KEY THEMES

• Letting setbacks reshape your path

• Building confidence through relationships

• Redefining success after loss

• Learning by starting small

Mat Parkins didn’t set out to build a business. His journey took him from kitchens to marketing, through personal setbacks and uncertainty, before finally stepping into entrepreneurship. Hear how he navigated risk, loss and reinvention, and what he learned along the way.

KEY THEMES

• Burnout as a turning point

• Testing ideas through personal experience

• Embracing risk and uncertainty

• Building inclusive, purpose-led businesses

What prompts someone to leave a secure job, and who do we become through the process? In this episode, three founders share candid stories of burnout, self-doubt and discovery, weaving together purpose, risk and the enduring drive to help others.

KEY THEMES

• Reinventing setbacks as new beginnings

• Community over lone heroics

• Building confidence through action

• Aligning business with personal values

What does it take to leave a predictable path, or create your own, when certainty is in short supply? This episode explores how Dom Tyler, Neil Chamroo, and Temini Kasumu each navigated the leap into entrepreneurship, facing setbacks, reinvention, and the courage to try things that might not work.

KEY THEMES

• Reinventing purpose after a career

• Embracing risk and uncertainty

• Building community around new ideas

• Developing new skills as a founder

What does it take to reinvent yourself as a founder? Episode 3 hears from Linda Blanchette and Tom West, who each moved from established careers into uncertain territory — and found new meaning by building businesses rooted in sustainability and community.

KEY THEMES

• Balancing ambition and family

• Growing organically with uncertainty

• Building confidence through experimentation

• Leading with values under pressure

After a corporate career in recruitment, Sarah McKee-Harris created her own path, building Kingswood Group from a spare-room startup into a growing HR firm. She shares candid lessons on risk, reinvention, and how founding can change us.