The Owners Outlook Podcast

Owners Outlook
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Owners Outlook is a podcast that dives deep into the journeys of successful entrepreneurs, business owners, athletes, and creators. Join us as we explore their stories, strategies, and insights on what it takes to truly ’own your success.’ Each episode offers real-life lessons, expert advice, and inspiring conversations to help you navigate your own path to success.

  1. 6d ago

    The Art of Enough: Catherine Hiller on Freedom, Creativity and Redefining Success

    In this episode of Owners Outlook, Shaun sits down with artist Catherine Hiller to explore what can happen when we stop following someone else’s definition of success and begin listening to what genuinely makes us feel alive. After studying art in Paris, Catherine spent 20 years building a successful career in advertising across the United Kingdom and Australia. She eventually worked her way into senior leadership, but as her responsibilities grew, so did the stress—and she found herself moving further away from the work and creativity she once enjoyed. Painting became Catherine’s way of processing that pressure. What began as a creative outlet in the evenings slowly attracted interest online, leading to exhibitions, commissions and growing demand for her work. Then, after returning from a Christmas break and realising she no longer cared about the problems she was being paid to solve, Catherine trusted her instincts, resigned that same day and became a full-time artist. She has never looked back. Here’s what you can expect from this episode: Trusting Your Instincts Catherine shares why some of the most meaningful decisions in her life were made before fear had the opportunity to take over. She reflects on leaving France for Australia at just 18 years old, accepting challenges throughout her advertising career and eventually walking away from a secure leadership position to pursue an uncertain creative path. Turning Experience Into Opportunity Although Catherine left advertising behind, she explains why those 20 years were never wasted. From understanding clients and managing commissions to marketing, social media, cash flow and running a business, the skills she developed in her previous career became an important foundation for her success as an independent artist. Creating From Passion, Not Pressure Catherine discusses why she has never painted simply to make money. For her, art is an intuitive form of expression—something she turns to when she is happy, stressed or processing life. She believes audiences can feel when work is authentic and that meaningful success often follows when the passion comes first. Designing a Life Around Freedom Rather than building the biggest business possible, Catherine has intentionally built a life that gives her time. Her mornings are often spent swimming, walking to the studio and painting. Her afternoons are left open for nature, friends, her dog and simply living. She explains why she has resisted opportunities that would create more revenue but also bring more administration, pressure and working hours. Letting Go of Other People’s Expectations Catherine opens up about the judgement she has faced as an artist—from people questioning whether her career pays the bills to assumptions that she must rely on someone else financially. Instead of allowing those opinions to define her choices, she has learned to trust herself, develop a thick skin and remain focused on the life she wants to live. Redefining What Success Looks Like For Catherine, success is not about status, money or constant growth. It is freedom, peace, meaningful time with the people she loves and the ability to make her own decisions. Her perspective invites us to ask an important question: if money and other people’s expectations were removed, how would we actually choose to spend our lives? Tune in for an honest and refreshing conversation about creativity, courage, trusting your gut and building a version of success you would be happy to live with for the rest of your life.

    The Art of Enough: Catherine Hiller on Freedom, Creativity and Redefining Success

  2. Jul 22

    The Artist Behind the Passion: Matilda on Creativity, Conservation and Owning Success

    In this episode of Owners Outlook, Shaun sits down with artist, graphic designer, storyteller and wildlife educator Matilda to explore what happens when a lifelong passion becomes more than a creative outlet—it becomes a career, a purpose and a way to contribute to something bigger. Matilda’s creative journey began almost as soon as she could hold a pencil. Drawing became her way of processing emotions, capturing the wildlife around her and expressing how she saw the world. What started as childhood curiosity eventually grew into published books, professional design work and a career built across illustration, storytelling and conservation education. But building a life around creativity hasn’t come without uncertainty. Matilda opens up about procrastination, burnout, freelancing, the pressure to constantly pursue the next achievement and the growing impact of generative AI on artists and designers. Through it all, she continues to return to the same driving force: a genuine love for her craft and a desire to use her creativity to give wildlife a voice. Here’s what you can expect from this episode: Turning Passion Into a Career How Matilda began drawing from an early age and used creativity as a form of expression and therapy. The childhood signs that she already had an entrepreneurial mindset. How writing and illustrating a children’s book at 13 showed her that a creative idea could become something real. Why completing one meaningful project can create the confidence to pursue bigger opportunities. Betting on Yourself The moment Matilda decided to take her creative work seriously and explore freelancing full-time. Why taking a risk doesn’t always mean having everything figured out. How she built momentum by working on her business outside of her regular employment. The importance of backing yourself—even when doing so feels uncomfortable or unrealistic. Procrastination, Productivity and Burnout Why creative people can become distracted by the excitement of their next idea. How deadlines, checklists and small wins help Matilda remain focused. The challenge of maintaining passion when creativity becomes your profession. Why rest and reflection are essential when you’re constantly pushing toward the next goal. Creativity in the Age of AI Matilda’s honest perspective on the rise of generative AI and its impact on artists. Why the value of creative work goes beyond the finished product. The passion, relationships and human experience that can’t be replicated through convenience alone. How artists can continue to differentiate themselves through authenticity, care and connection. Wildlife, Conservation and Purpose How Matilda combines illustration, storytelling and wildlife education. Why she feels responsible for speaking on behalf of animals and plant species that cannot speak for themselves. The importance of drawing attention to lesser-known species—not only the animals that traditionally receive the spotlight. How education can create curiosity, compassion and a desire to protect the natural world. Redefining Success Why high achievers often reach one mountain and immediately begin looking toward the next. Matilda’s experience of being highly driven while struggling to recognise how far she has already come. The role journaling, mindfulness and positive self-talk can play in acknowledging progress. Why owning your success can mean feeling content, happy and proud of the work you’re contributing to the world. What I took from this conversation is that passion isn’t always loud or effortless. Sometimes it looks like finishing the project, taking the risk, pushing through uncertainty and remembering why you began. For Matilda, success isn’t simply about how many projects she completes. It’s about creating meaningful work, contributing to something greater than herself and learning to appreciate the journey while still remaining open to what might come next.

    The Artist Behind the Passion: Matilda on Creativity, Conservation and Owning Success

  3. Jul 8

    The Man After the Game: Tom Rockliff on Fatherhood, Sobriety and Success

    In this episode of Owners Outlook, Shaun Lord sits down with Tom Rockliff — former Brisbane Lions captain, All-Australian, 208-game AFL player, and founder of Rockliff Finance — for an honest conversation about football, resilience, identity, fatherhood, business, and what success really means after the crowd fades. Tom opens up about growing up in country Victoria, chasing an AFL dream that was never guaranteed, overcoming setbacks, and building a career through hard work, self-belief, and determination. But this conversation goes well beyond footy. Tom reflects on the pressure of leadership, the mental challenges of professional sport, his journey through divorce, sobriety, psychology, and learning how to become a better version of himself — not just for business or success, but for his two boys. Here’s what you can expect from this episode: The Journey to AFLGrowing up in the country and falling in love with sport.Breaking his leg at 16 and being overlooked in multiple drafts.How hard work, boxing, and mindset helped him build a 208-game AFL career. Leadership, Pressure and PerspectiveBecoming captain of the Brisbane Lions at a young age.The lessons Tom learned from leading through difficult years.What he would do differently now with more self-awareness and perspective. Mental Health, Sobriety and GrowthWhy Tom leaned into psychology after a difficult divorce.The importance of training the mind, not just the body.How giving up alcohol changed his clarity, energy, fatherhood, and outlook on life. Life After Football and Rockliff FinanceHow Tom transitioned from AFL into finance broking.Why helping people find solutions gives him more fulfilment than football ever did.The value of fighting for clients when others have put them in the “too hard” basket. Owning Your Own SuccessWhat success meant to Tom as an AFL player.Why success now looks more like purpose, contentment, routine, resilience, and being a present father.The quote that now guides his life: “Yesterday is history, tomorrow is a mystery, today is a gift — use it.” This is a conversation about the person behind the player — the setbacks, the lessons, the quiet work, and the perspective that comes from rebuilding yourself. Tune in for an honest and grounded episode with Tom Rockliff on what it really means to own your own success.

    The Man After the Game: Tom Rockliff on Fatherhood, Sobriety and Success

  4. Jul 1

    Beyond the Spotlight: Comedy, Meditation and Owning Success with Anthony

    In this powerful episode of Owners Outlook, Shaun sits down with comedian Anthony as he opens up about a life-changing year, a near-death experience in Canada, and the 10-day silent Vipassana meditation retreat that reshaped the way he views success, ego, creativity, and personal healing. Known for making people laugh, Anthony brings a deeply reflective perspective on what happens behind the performance — the pressure, the self-talk, the ambition, and the emotional cost of chasing external success. Here’s what you can expect from this episode: A Life-Changing Turning PointAnthony shares the story of nearly freezing to death in Canada after a show, the difficult season that followed, and how those events led him to Vipassana meditation. The Power of Meditation and Self-AwarenessAnthony breaks down the intensity of a 10-day silent retreat, what it taught him about the mind and body, and how daily meditation has helped him build a stronger line of defense against anxiety, anger, fear, and old patterns. Comedy, Ego, and the Pursuit of SuccessFrom leaving a career in insolvency accounting to becoming a touring stand-up comedian, Anthony reflects on how ego initially drove his ambition — and why external achievements did not bring the fulfillment he expected. Using Comedy to Give BackAnthony explores how comedy can become more than entertainment. He explains how laughter can disarm people, create connection, and become a way to share deeper ideas through humour. Redefining What Success MeansIn one of the most honest answers to the Owners Outlook signature question, Anthony challenges the word “success” itself and offers a grounded reminder that success is not always money, awards, or recognition — sometimes it is connection, presence, and walking away from a conversation feeling like something meaningful was shared. Tune in for a raw, thoughtful, and unexpectedly moving conversation about ego, healing, laughter, discipline, and what it really means to own your own success. Chapters:0:00 Introduction0:09 Anthony’s near-death experience in Canada1:02 Discovering Vipassana meditation3:34 The 10-day silent retreat experience5:22 Building an emotional “secretary” through meditation8:25 From insolvency accountant to stand-up comedian12:20 Early ambition and building a comedy career14:20 The emptiness behind external success18:46 Ego, achievement, and personal collapse21:02 Why Anthony almost quit comedy22:02 Using comedy to give to others25:41 Comedy as a Trojan horse for deeper ideas34:18 Daily habits, meditation, writing, and discipline41:31 Why laughter matters46:09 The Owners Outlook signature question46:50 Anthony’s definition of success57:27 The Vipassana course and final reflections59:20 Closing remarks

    Beyond the Spotlight: Comedy, Meditation and Owning Success with Anthony

  5. Jun 17

    The Art of Evolving: Creativity, Motherhood and Owning Success with Natalie Martin

    In this episode of Owners Outlook, Shaun sits down with artist, entrepreneur, educator, and travelling creative Natalie Martin for a raw and honest conversation about creativity, resilience, motherhood, business, and what it really means to build a life around your passion. Natalie’s journey started long before she confidently called herself an artist. From selling old treasures to her younger brothers as a kid, to launching an early fashion label at university, working in graphic design, building a creative business, and now travelling Australia in a caravan with her family while teaching watercolour workshops — her story is one of evolution, courage, and learning to back herself through every season. But this conversation goes deeper than business. Natalie opens up about the challenges of running a creative business, the lessons that came from a difficult business partnership, the reality of being a mum while chasing creative work, and the major ankle injury that left her in hospital, unable to drive, on crutches for months, and forced her to rely on others in a way she never had before. Here’s what you can expect from this episode: Creativity, Business and EvolutionNatalie shares how she went from graphic design to building a life as an artist, and why creative people need to allow themselves to grow, shift, and evolve over time. The Reality of Running a Creative BusinessFrom multiple income streams to online courses, workshops, artwork, e-commerce and teaching, Natalie explains what it really takes to make a living from your art — and why there is no fast track. Resilience Through Injury and MotherhoodNatalie reflects on the hardest 12 months of her life, including grief, trauma, a serious ankle injury, raising two young boys, and learning how to ask for help when independence was no longer enough. Finding Purpose Through TeachingNatalie speaks beautifully about the joy of helping people reconnect with creativity, especially those who may not see themselves as creative at all. Owning Your Own SuccessIn the final part of the conversation, Natalie shares a powerful perspective on success — not as a destination, but as something we need to pause, acknowledge, celebrate, and share along the way. This episode is a reminder that success isn’t always about arriving somewhere perfect. Sometimes it’s about looking back at every lesson, every mistake, every hard season, and realising they all played a part in shaping who you are today. Tune in for an honest, thoughtful and inspiring conversation with Natalie Martin on creativity, resilience, identity, and owning the journey you’re already on. Chapters:0:00 Introduction0:08 Natalie’s early creative and entrepreneurial journey2:29 Leaving a dream job to build her own business4:48 Injury, grief, motherhood and resilience8:50 Learning to accept help10:21 The sacrifices behind chasing a dream12:19 Reframing mindset through pain and recovery14:24 Natalie’s first business and early lessons15:47 Walking away from a business partnership19:53 Building multiple streams of income as an artist21:46 Advice for up-and-coming creatives26:50 Habits and routines that support creativity29:39 Creating while travelling Australia32:20 Discovering the joy of teaching35:27 Learning to call herself an artist39:23 What owning your own success means to Natalie

    The Art of Evolving: Creativity, Motherhood and Owning Success with Natalie Martin

  6. Jun 11

    From Bedroom Startup to Business Empire: Building, Winning and Taking Ownership with Nick Bell

    In this episode of Owners Outlook, Shaun sits down with Nick — entrepreneur, investor, Shark Tank Australia judge, and founder behind multiple successful businesses — for a raw and honest conversation about business, resilience, ego, money, mistakes, and what it really means to take ownership of your own success. Nick’s story starts well before the big exits. From selling school lunches and sports equipment in high school, to building a skincare business that left him earning just $100 a week, his journey is one of hunger, hard lessons, and refusing to stay down. After years of struggle, Nick started a digital marketing business from his bedroom — cold calling across New Zealand and Australia, learning every part of the business, and eventually growing it into a company he sold for $39 million. But as Nick shares, the wins didn’t come without pressure, mistakes, public criticism, failed investments, and some very tough moments behind the scenes. Here’s what you can expect from this episode: From Struggle to ScaleNick shares how he went from losing money in his first business to making $10,000 in three days and scaling rapidly from his bedroom. The Reality of Business GrowthShaun and Nick unpack what happens when a business grows too fast without structure, systems, and the right people in place. Lessons From Losing MillionsNick opens up about failed investments, being burned by people he trusted, and why he now backs himself more than anyone else. Taking OwnershipA powerful conversation about responsibility, avoiding the victim mentality, knowing your numbers, and why the person at the top must take full accountability. The Shark Tank PerspectiveNick shares what he looks for in entrepreneurs within the first few minutes of a pitch, and what most business owners miss when trying to grow. Building for Cash Flow, Not Just ExitNick explains why he focuses on profitable, cash-flow-positive businesses — and why he never starts a business purely to sell it. This episode is full of honest reflections, sharp business lessons, and real-world perspective from someone who has lived the highs and lows of entrepreneurship. Maybe the biggest takeaway is this: success is not just about money or the exit. It is about building something, learning from the hard moments, taking responsibility, and finding what genuinely drives you. Tune in to hear Nick’s story and reflect on the question we ask every guest: What does it mean to own your own success? Chapters:0:00 Introduction2:14 From struggle to $1 million in three months4:13 Building resilience after losing everything8:21 Growing too fast and learning the hard way14:14 Life after a $39 million exit16:20 What makes a business truly thrive23:01 The lows, failed investments, and tough lessons32:51 Habits, productivity, and working with speed36:39 Building multiple businesses at once49:15 Lessons from Shark Tank Australia56:43 What it means to own your own success

    From Bedroom Startup to Business Empire: Building, Winning and Taking Ownership with Nick Bell

  7. May 27

    Country Roots to World Stage: Barry Lester on Belief, Support & Owning Success

    In this inspiring episode of Owners Outlook, Shaun Lord sits down with Australian lawn bowls champion Barrie Lester to explore a life shaped by sport, resilience, community, and gratitude. From growing up in a small country town in Victoria to representing Australia on the world stage, Barrie shares the moments that shaped his journey — the early competitive fire, the mentors who believed in him, the heartbreak of losing his mum, and the mindset that helped him turn the page and keep moving forward. Here’s what you can expect from this episode: Growing Up with a Competitive SpiritBarrie reflects on his childhood in country Victoria, where sport became part of his identity from a young age. Whether it was football, swimming, handball or lawn bowls, he carried a deep desire to give everything his best shot. The Power of Mentorship and CommunityBarrie shares how the Lakes Entrance Bowls Club, his mentor John Snell, and the wider bowls community helped shape not only his career, but the person he became along the way. Turning Pain into PurposeAfter the sudden passing of his mum, Barrie opens up about grief, rebuilding, and the decision to move to Melbourne to chase his dreams — carrying her memory with him every step of the way. Mindset, Preparation and LongevityBarrie speaks about what it takes to perform at the highest level for nearly two decades, from preparation and self-belief to learning how to handle pressure, judgment and setbacks. What It Means to Own Your SuccessFor Barrie, success isn’t something you keep to yourself. It’s something you share with the people who helped you get there — the mentors, friends, family, teammates and supporters who played a part in your journey. Tune in for a heartfelt conversation about resilience, gratitude, perspective, and why no achievement is ever truly won alone.

    Country Roots to World Stage: Barry Lester on Belief, Support & Owning Success

  8. May 20

    Purpose Over Pressure: Trent Falson on Service, Courage & Owning Success

    In this episode of Owners Outlook, Shaun sits down with Trent Falson, a fourth-generation Bondi local, Bondi lifeguard, former Australian surf lifesaving champion, and someone whose life has been shaped by service, pressure, purpose and community. Trent shares his journey from growing up in the water at Bondi, to becoming a lifeguard at just 18, and the reality of stepping into a role where life-changing decisions often happen in seconds. From dealing with fatalities early in his career, to supporting others through trauma, Trent opens up about the mental weight of first responder work and the importance of speaking up, seeking help and learning how to truly listen. Here’s what you can expect from this episode: Growing Up in Bondi Trent reflects on his childhood as a fourth-generation Bondi local, his early years in the ocean, and how surf lifesaving shaped his identity from a young age. Life as a Bondi Lifeguard From rescues and medical emergencies to moments of chaos and calm, Trent shares what it really takes to show up when people need you most. Mental Health, Trauma and Listening Trent speaks honestly about the emotional toll of first responder work, early signs of PTSD, and why sometimes the most powerful thing we can do for someone is simply listen. Purpose Over Status After stepping into the corporate world, sales, buyer’s agency and real estate, Trent realised that money and status could never replace the feeling of doing work that truly mattered. Owning Your Success For Trent, success means waking up each day, looking in the mirror, and feeling genuinely aligned with the person looking back. Tune in for a thoughtful and honest conversation about courage, purpose, slowing down under pressure, and what it means to build a life that actually feels right.

    Purpose Over Pressure: Trent Falson on Service, Courage & Owning Success
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About

Owners Outlook is a podcast that dives deep into the journeys of successful entrepreneurs, business owners, athletes, and creators. Join us as we explore their stories, strategies, and insights on what it takes to truly ’own your success.’ Each episode offers real-life lessons, expert advice, and inspiring conversations to help you navigate your own path to success.

Information

  • Creator
    Owners Outlook
  • Years Active
    2024 - 2026
  • Episodes
    59
  • Rating
    Explicit
  • Copyright
    © Owners Outlook
  • Show Website
    The Owners Outlook Podcast