Greg Sheehans Podcast

Greg Sheehan

The crazy nature of early stage startups (the uncertainty, the doubters, the rejection) can be similar to the forces felt by those who at some point in their lives felt the need to make seismic shifts in their personal worlds.

My aim as your host is to bring the raw stories of startup failure and fuckup, alongside the inspirational messages of encouragement, tips and suggestions.

Alongside the business chats we will also hear stories from people living interesting and inspirational lives.

The podcast is recorded alongside the beautiful ocean beach of Mount Maunganui, New Zealand, but our guests and their experiences will be from around the world.

Thanks for your support of the show.

Greg Sheehan



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Episodes

Ep 37: Kat Webber: CoFounder and CEO of LiveRem and ResolvePay
6d ago
Ep 37: Kat Webber: CoFounder and CEO of LiveRem and ResolvePay
Send us a Text Message.Ever wondered how to transition from a corporate career to thriving as a serial entrepreneur? Kat Webber, the founder of LiveRem and ResolvePay, joins us to share her journey of resilience, creativity, and relentless pursuit of her entrepreneurial dreams. From her early ventures in dog walking and a spray tanning business, to launching an innovative Christmas tree enterprise in university, Kat's story is a testament to the power of self-belief and a strong support system. Discover how she turned her corporate experience into a stepping stone for bootstrapping successful SaaS businesses.Curious about the nuts and bolts of building a bootstrapped SaaS business from the ground up? Kat reveals her strategies for understanding customer needs, balancing multiple priorities, and maintaining flexibility without external capital. She provides candid insights into the trials and triumphs of managing three businesses, raising young children, and even building a house amid financial constraints. We'll also explore the valuable lessons she's learned about progressive hiring practices, addressing unconscious bias, and the Know Your Gap initiative focused on gender pay gaps and representation.Kat’s deep connection to her Irish heritage and her journey from city life to a peaceful coastal existence add another layer to her inspiring story. We discuss the importance of community and how remote work and a supportive tech community have enriched her life. Kat’s experiences underline the significance of embracing failure as a learning opportunity, choosing the right business partners, and fostering a balance between motherhood and entrepreneurship. Whether you're navigating the startup world or balancing personal and professional responsibilities, Kat’s story offers practical tips and inspiration for achieving success under demanding circumstances.Connect with Kate personally or via ResolvePay or LiveRem
Ep 36: Michael Wood: From $0 to selling for hundreds of millions
May 24 2024
Ep 36: Michael Wood: From $0 to selling for hundreds of millions
Send us a Text Message.When Michael Wood, the entrepreneurial force behind Translucent and ReceiptBank (Dext), sits down to chat, you're guaranteed a treasure trove of insights that go beyond the usual startup success story. As we navigate Michael's voyage from the uncharted waters of early B2B SaaS business terrain to the heights of a multi-hundred million dollar sale, his candour is as refreshing as it is enlightening. His reflections on the motivations fuelling his drive shed light on the personal challenges that often accompany the entrepreneurial journey. Michael's backstory, influenced by his mother's conservative take on job security, makes his leap into entrepreneurship all the more compelling.But this conversation isn't confined to past victories; Michael leads us through the emotional labyrinth of founding a company, from the adrenaline rush of overcoming the brink of bankruptcy to the nuanced struggle of expanding across international borders. The story of ReceiptBank's metamorphosis from a postal-based service to a digital lifesaver for accountants is a masterclass in adaptation and innovation. And with Translucent's inception sparked by the need for seamless multi-entity management, Michael proves that the entrepreneurial itch doesn't simply fade with success—it evolves.Away from spreadsheets and investor meetings, Michaels shares how he recharges with adventures that rival his business conquests. From sailing the Atlantic to cycling the rugged terrains from Melbourne to Sydney, his pursuits speak to the resilience and relentless spirit that define a true founder. You can connect with Michael here and be sure to check out both ReceiptBank and Translucent.
Ep 33: Anna Scheirlinck: Alpine Rescuer - A Life of Service and Leadership
May 20 2024
Ep 33: Anna Scheirlinck: Alpine Rescuer - A Life of Service and Leadership
Send us a Text Message.Embark on a riveting journey with our guest Anna Scheirlinck, whose life reads like an adventure novel, brimming with courage and a relentless drive to make a difference.From academia to the frontlines of law enforcement and disaster relief, Anna's tale is not just one of career changes but of chasing the greater good, regardless of the terrain.Her experiences stretch from the lecture halls of social policy to the dusty streets of Alice Springs, and from the earthquake-struck streets of Christchurch to the snowy peaks of New Zealand's mountain ranges. Anna's story is a testament to the human spirit's capability to adapt, serve, and lead in the most demanding circumstances.My conversation with Anna isn't just about her past glories; it's a deep dive into the ethics of policing, the essence of community service in crisis, and the raw leadership honed in military and mountaineering feats. She unearths the nuances of serving as a constable in an outback town, the human connections that can evolve from disaster recovery, and the relentless physical and mental trials faced in both army training and alpine rescues. Anna's narrative is a powerful reminder of the strength found in vulnerability, the leadership born out of service, and the adrenaline that fuels a life dedicated to surmounting both literal and figurative mountains.As we conclude our episode, Anna's voice brings us into the heart of alpine search and rescue operations, where the stakes are as high as the peaks. With humility and raw honesty, she opens up about the support systems that uphold her and her team, the culture of debriefing that they rely on, and her dreams of scaling New Zealand's formidable 3,000-metre summits. You can connect with Anna here.
Ep 32: Andy Kerr: Being honest about our own Mental Health
May 12 2024
Ep 32: Andy Kerr: Being honest about our own Mental Health
Send us a Text Message.When we peel back the layers of our lives, we often find shared battles and common ground in the quest for mental wellness. Today, we sit down with the remarkably open Andy Kerr, who walks us through his journey of loss, depression, and the eventual solace he finds in helping others and in the written word. His story is a poignant reminder that while suffering may be deeply personal, the struggle with mental health is a universal challenge that unites us all.Writing proved to be Andy's lifeline, a therapeutic outlet that eventually took the shape of his book "We All Change." He recounts the rollercoaster of emotions that led to its creation and discusses the surprising realizations about life's purpose that emerged from his introspective chapters. This conversation is an honest exploration of the struggles with mental health, the continuous management of well-being, and the importance of supportive dialogues that shatter the stigma surrounding mental health issues.Andy's resilience also shines through in his passion for running, which goes much beyond a mere physical pursuit. Each stride for Andy represents a step in his ongoing recovery, echoing the determination and community found in the running scene. The discussion doesn't shy away from the physical challenges and injuries that come with age, yet it's imbued with optimism about setting and achieving new goals. Andy's narrative is a testament to the strength found in vulnerability and a beacon of hope for those navigating the murky waters of mental health.You can read Andy's writings via his Substack page.His charity website can be found here or email defirippleeffects@gmail.com.If you'd like to purchase a copy of his book (remember a donation is made to the I AM HOPE charity whenever a copy of a book is purchased) then you can contact Andy at DifferentPeopleBooks@gmail.com.
Ep 31: Dr. Johann Malawana: From the Frontlines of Medicine to the Forefront of Startups
May 11 2024
Ep 31: Dr. Johann Malawana: From the Frontlines of Medicine to the Forefront of Startups
Send us a Text Message.Ever feel like you're standing at the edge of a precipice, about to make a decision that could change everything? That's where Dr. Johann Malawana found himself as he made the audacious leap from the security of medicine to the exhilarating world of startups. On today's show, he bares his soul, revealing the internal battles, self-doubt, and the resilience required to navigate such a life-altering transition. His candid reflections on the pressures of entrepreneurship, juxtaposed with his experiences in obstetrics, make for a compelling narrative that both aspiring and seasoned founders can relate to.As we weave through Johann's story, the conversation gets into the challenges of leading two mission-driven healthcare organisations, The Healthcare Leadership Academy and Medics Academy. His insights on the importance of focus and the similarities in decision-making between medicine and business leadership are eye-opening. Johann provides an inspirational roadmap for those contemplating a foray into startups. He encourages aligning one's personal convictions with their career choices, emphasising that the true measure of success is deeply personal and unique to each individual. Embrace the doubt, harness the passion, and carry forward the mission—Dr. Johann Malawana's reflections are a beacon for anyone seeking to leave a mark on the world through their work.
Ep 23: Dr Leo Evans: The Profound Journey of a UK Educational Entrepreneur
Apr 18 2024
Ep 23: Dr Leo Evans: The Profound Journey of a UK Educational Entrepreneur
Send us a Text Message.Dr. Leo Evans is an inspiration.From his humble beginnings in Dorset to becoming a Forbes 30 under 30 honoree, Leo's tale is one of ambition fuelled by early financial challenges. His story unfolds from a scholarship at a prestigious UK boarding school to his innovative leap into founding "The Profs" with his brother.We dig into what truly matters in life as Leo opens up about his massive career pivot, from the high-pressure trading floors of JP Morgan to the liberating journey of entrepreneurship. His candid reflections on the realization that wealth does not equate to happiness illuminate the deeper motivations that drive us. We uncover the wisdom of mentorship, the strength found in personal development, and the courage it takes to turn away from a lucrative career to forge a path that brings fulfillment beyond monetary gain.Leo gives us an insider look at the inner workings of a successful startup. We delve into the transformative power of digital marketing but look at how to play nicely with the large global platforms. Leo leaves us with profound insights into the value of calculated decision-making, the delicate balance between intuition and analysis, and how redefining success on your own terms can lead to life-changing outcomes. Don't miss this episode as Dr Leo shares his remarkable journey, offering priceless lessons for any aspiring entrepreneur or student looking to chart their own course.You can connect with Dr Leo via LinkedIn and check out The Profs.
Ep 18: Ben Gleisner - The Visionary Founder and CEO of Cogo
Mar 28 2024
Ep 18: Ben Gleisner - The Visionary Founder and CEO of Cogo
Send us a Text Message.I couldn't help but be inspired as Ben Gleisner, founder of Cogo as he takes us through his Eco-conscious tech journey—a transformation from being an economist in central government to becoming a voice for sustainable change as an entrepreneur. With a minimalist approach, Ben's life story is a compelling testament to how individual philosophies can shape a purpose-driven career. Tune in to discover how this economist turned his frustration with slow governmental change into a technology that nudges individuals and SMEs towards reducing their carbon footprint, redefining what it means to be successful in business.Imagine a world where companies are celebrated not just for their financial value but for their positive impact on the planet. Ben introduces us to the concept of 'Gigacorns' and takes us behind the scenes of Cogo's global expansion, shedding light on the challenges and strategies of nurturing a company culture without borders. It's a fascinating glimpse into the world of a tech company that's as concerned with reducing carbon emissions as it is with maintaining a healthy, vibrant workplace. This episode is an eye-opener for anyone curious about the collision of entrepreneurship and environmental activism.We wrap up with a reflection on the philosophy of minimalism and the joy found in a decarbonized lifestyle. Ben's personal journey is an invitation to consider how our responses to climate change can enrich rather than restrict our lives. He champions a shift in perspective, where tackling climate change paves the way for a better quality of life—less materialistic, more family-oriented, and grounded in sustainable living. It's more than just an interview; it's a challenge to each of us to consider our own impact and the legacy we wish to leave behind.Connect with Ben on LinkedIn and check out Cogo.