What if your biggest career breakthrough came from breaking your own rules about what “success” is supposed to look like? On this episode of Legendary Leaders, Cathleen O’Sullivan sits down with serial entrepreneur Joe Zentmyer for an honest, wide-ranging exploration of pivots, reinvention, and leading with genuine passion.

With over two decades of experience spanning Fortune 500 sales, food manufacturing, rock climbing gyms, and now a thriving aquarium supply business, Joe’s unconventional story is living proof that authentic curiosity and adaptability trump following “the script.” If you’ve ever held yourself back from a new opportunity because it didn’t fit the usual definition of success, this episode is for you.

Cathleen and Joe unpack the mindset shifts, resilience, and hard-won lessons that come with building (and sometimes rebuilding) teams and businesses from scratch. From learning the art of self-awareness and dealing with rapid change, to rebuilding after a crisis and keeping the entrepreneurial spark alive, this conversation will inspire you to take bold steps even (or especially) when the path is unconventional.

Episode Timeline Highlights:

06:36 From corporate life to becoming a climbing entrepreneur

13:21 Entrepreneurial life - you need to embrace the unknown

16:55 Performance problems are often leadership issues, not just HR

25:18 Climbing gym staff protests

31:01 Leaders can lack perspective in the midst of a crisis

33:22 Overcoming work overload: Need to find balance

40:46 Rediscovering leadership passion, post-Covid lockdowns

46:26 Passion-driven marketing and staffing

54:26 Hiring challenges for small businesses

01:01:40 Entrepreneurs need to embrace long-term optimism

Key Takeaways:

• True success in leadership and business is not one-size-fits-all; embracing your own curiosity and passion is the best guide.

• Building great teams starts with self-awareness, clear expectations, and prioritising attitude over technical skills.

• Crisis reveals character: resilience, honest communication, and willingness to learn from setbacks will define your leadership.

• Entrepreneurship isn’t for everyone the risks and rewards are real. Understand your motivations, know your limits, and be willing to reflect and reset.

• Protect your passion by delegating, innovating, and making time for self-reflection—don’t let the business become all-consuming.

ABOUT Joe Zentmyer:

As a serial entrepreneur with more than 20 years of experience, Joe builds businesses by developing business managers along with systems that support those managers. He’s very proud of the many young professionals he has mentored during his career. Joe’s diverse business experience from food manufacturing to rock climbing gyms, gives him a unique perspective and ability to creatively assess every opportunity. He loves the process of creating a business and turning a concept into a profitable reality. Before launching Snaggletooth Goby, Joe c-ofounded First Ascent, a Chicago-based climbing and fitness chain. From 2013 to 2022, his partners, investors, and himself grew the business to seven locations in multiple markets. Each location was 20,000 to 50,000 square feet in size. They achieved this rapid growth by partnering with lenders, landlords and key vendors to identify and develop only the best locations.

Connect with Joe:

Website: snaggletoothgoby.com

LinkedIn: https://www.linkedin.com/in/joe-zentmyer/

Connect: 


Find | Cathleen O’Sullivan

Business: cathleenmerkel.com

Email: cmc@cathleenmerkelcoaching.com

LinkedIn: https://www.linkedin.com/in/cathleen-merkel/

Instagram: https://www.instagram.com/legendary_leaders_cathleenos/

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What if the working world wasn’t designed for you, and following the rules held you back from the leadership and life you actually want? In this episode of Legendary Leaders, Cathleen welcomes Nyree Ambarchian, co-founder of purpose-led communications agency Jack & Grace, for a bold and honest conversation about ditching outdated workplace norms and rewriting the “rules” of work.

Nyree shares her journey from diligently following the rules to challenging and rewriting them, both in her own career and in building her business.

This episode is a must-listen for anyone ready to question inherited workplace “rules,” embrace authentic leadership, and create environments where people and planet can thrive.

Episode Timeline:

01:35 What might happen if we stopped following outdated workplace rules and started making work fit us instead?

07:56 Launching her purpose-led communications agency during the lockdowns leveled the playing field

10:44 Motherhood led Nyree to reevaluate workplace norms

13:29 Personal challenges with miscarriage and infertility

18:09 Support for miscarriage should never be a one-size-fits-all policy

25:02 Jack & Grace founded as an experiment to challenge industry norms

27:33 Why unlimited holidays didn't work at Jack & Grace

29:24 Salary transparency is a powerful tool for reducing inequality

37:20 All jobs at Jack & Grace are offered part-time as standard

49:50 Measuring success not just by profit, but also people and planet

Key Takeaways:

• Most workplace “rules” weren’t designed for the modern workforce and often exclude, rather than empower people.

• Open conversation about real-life challenges like miscarriage and menopause can transform organisational culture and support.

• Experiments in flexibility, salary transparency, and inclusive hiring aren’t just “nice” they drive retention, talent attraction, and genuine well-being.

• Measuring success by profit alone ignores the vital health of people and the planet - embrace the triple bottom line.

ABOUT Nyree Ambarchian:

Nyree Ambarchian is a Co-Founder of Jack & Grace, a purpose-driven communications agency. On a mission to use comms as a force for good, Jack & Grace is a B Corp and only works with organisations that value people, planet, and profit equally. Nyree has twenty years experience in communications, specialising in behaviour change campaigns, delivering work for the likes of Riverford, the Duke of Edinburgh's Awards, and Defra. Having obediently followed the ‘rules’ of work all her career, in 2018, Nyree became a mum. Finding herself no longer able to stick to ‘the rules’, the burn of failure hit hard. Until she realised the problem wasn’t her, it was the rules. That marked the start of her journey to rewrite the rules of work, so they work for more people.

Connect with Nyree :

LinkedIn: https://www.linkedin.com/company/jackandgrace/

Instagram: https://www.instagram.com/jackgracecomms/

Website: https://www.jackandgrace.co.uk/

Connect: 


Find | Cathleen O’Sullivan

Business: cathleenmerkel.com

Email: cmc@cathleenmerkelcoaching.com

LinkedIn: https://www.linkedin.com/in/cathleen-merkel/

Instagram: https://www.instagram.com/legendary_leaders_cathleenos/

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What if burnout wasn’t a personal failure, but a sign that something bigger at the system level needs to change? In this episode of Legendary Leaders, host Cathleen O’Sullivan sits down with Kelly Swingler, the renowned “burnoutologist” and founder of the Burnout Academy, to uncover the truth behind today’s burnout epidemic. With candour and compassion, Kelly challenges the norms that glorify stress and exhaustion, exploring why real burnout is so much more than long hours. It’s about broken systems, shame, and outdated definitions of success.

Together, Cathleen and Kelly dive into the emotional realities of burnout, breaking down stigma and sharing personal stories of their own experiences. You’ll discover why leaders are often the first to “burn the brightest and break first,” and how shifting our focus from individual fixes to systemic change is the real path to sustainable well-being at work. Filled with vulnerability, laughter, and bold truths, this episode offers both insight and a call-to-action: it’s time to stop treating burnout as a weakness and start building workplaces and lives where well-being isn’t just an afterthought.

Episode Timeline:

03:27 Introducing Kelly Swinger, the "burnoutologist".

07:29 Burnout is the debilitating result of chronic stress

14:10 Leaders often misinterpret feeling overwhelmed or struggling as incompetence

19:47 Burnout is a global issue often caused by toxic workplaces

25:48 Living an unhealthy lifestyle can't be offset by minimal healthy activities

32:48 Many avoid discussing mental health as workplace stress rises

33:45 Burnout is often masked by other conditions due to stigma

56:27 Workplace freedom and creativity could reduce toxicity

01:07:35 Stressed leaders repeat outdated patterns

01:13:08 Leaders should focus on self-awareness and personal values over profits

01:20:20 Self-care routines can't cure burnout without genuine presence

01:24:49 Self-awareness and inner work are ongoing, challenging but rewarding.

Key Takeaways:

• Burnout is not just chronic stress or exhaustion, it’s falling off the edge of your stress scale into a place that affects your whole life.

• Leaders and organisations must move beyond surface-level “well-being” fixes and tackle the root causes of systemic burnout.

• You can’t “self-care” your way out of burnout, lasting transformation requires stopping, reflecting, and doing the deep inner work.

ABOUT Kelly Swingler

Kelly is the Burnoutologist, empowering Leaders to Banish Burnout in the changing world of work for themselves and their people. She leads the world’s number one Burnout Academy, training in Burnout Awareness. Known for being a rebel and a rule-breaker, Kelly has been ripping up the rulebook since 2002 after realising

that the way we are working isn't working, and how we are taught to define success is outdated. Today, Kelly educates leaders, Coaches HR and managers from companies around the world on how to recognise, prevent and recover from Burnout.

Connect with Kelly:

The Burnout Academy: https://www.kellyswingler.com/burnoutacademy

Book: https://www.kellyswingler.com/fckburnout

Social Media Links:

LinkedIn: https://www.linkedin.com/in/kellyswingler/

Instagram: https://www.instagram.com/iamkellyswingler/

YouTube: https://www.youtube.com/channel/UC9Z6iJPB4gYz1MZoUPOgdlQ

Connect: 


Find | Cathleen O’Sullivan

Business: cathleenmerkel.com

Email: cmc@cathleenmerkelcoaching.com

LinkedIn: https://www.linkedin.com/in/cathleen-merkel/

Instagram: https://www.instagram.com/legendary_leaders_cathleenos/

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What if your greatest legacy isn’t what you build, but who you build with along the way? In this episode of Legendary Leaders, your host, Cathleen O’Sullivan, invites you into a candid conversation with Nick Peel, a leader whose career spans some of the world’s most ambitious projects, from Arsenal Football Club to the cutting-edge NEOM "Line" project in Saudi Arabia. You’ll hear how Nick’s human-first approach to leadership has empowered teams to thrive under pressure, transcending titles and status in favour of authenticity, humility, and genuine impact. Together, they explore why self-awareness, openness to failure, and the courage to lead with empathy are at the heart of truly legendary leadership. Tune in to discover how embracing your humanity and building others up may just be the most powerful legacy you leave behind.

Episode Timeline:

00:00 Introduction

11:51 Embracing innovation and tackling ambitious projects

15:48 The importance of authenticity and being human in leadership

20:16 Learning from failure and the power of reflection

32:06 Building a strong, supportive family while leading global projects

38:09 Leading high-performing teams through empowerment and simplicity

44:22 The origins of NEOM’s The Line: bold ideas and collaboration

52:03 Leading diverse teams and unlocking innovation through trust

57:31 Supporting women’s leadership for future generations

Key Takeaways:

• Nick shares stories of nurturing talent and pride in seeing former colleagues grow, highlighting the importance of building others up on your leadership journey.

• Nick discusses the value of showing up authentically, empowering diverse teams, and leading with humility, whether in the high-pressure corporate world or ambitious projects like NEOM’s "The Line".

• Nick’s career, shaped more by "default than design," showcases how adaptability, curiosity, and learning steer personal and professional growth. He talks of the importance of reflection, being open to new ideas and leveraging lessons from both success and failure.

ABOUT Nick Peel

Nick has over 30 years of senior commercial and operational leadership expertise under his belt with esteemed organisations like Arsenal FC, LandSec, Battersea Power Station, McArthur Glen Designer Outlets, and Morrison Supermarkets. He has also held Non-Exec roles with a number of entities, including UCI World Cycling Championships, Streetwork charity, and Icons.com. His career spans retail, hospitality, property / real estate and sports, which he confesses is more by default than by design.

Nick is currently Director of Operational Readiness for THE LINE, the futuristic city under development at NEOM in Saudi Arabia. He specializes in building high performance teams, creating go to market strategies, building the new, and fixing the broken. He prides himself on a ‘ human first ‘ leadership style, and is motivated by change, learning, travel, and in particular his family and children.

Connect with Nicholas:

LinkedIn: https://www.linkedin.com/in/nick-peel-a5943a9?utm_source=share&utm_campaign=share_via&utm_content=profile&utm_medium=ios_app

Connect: 


Find | Cathleen O’Sullivan

Business: cathleenmerkel.com

Email: cmc@cathleenmerkelcoaching.com

LinkedIn: https://www.linkedin.com/in/cathleen-merkel/

Instagram: https://www.instagram.com/legendary_leaders_cathleenos/

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Is leadership about going it alone, or could sharing the load lead to even greater success? In this episode of Legendary Leaders, host Cathleen O'Sullivan welcomes the dynamic duo Clare Freshwater-Turner and Annabelle Richards to explore how job sharing could be the key to enhanced leadership and personal fulfilment. Clare and Annabelle, senior managers in sustainable business at Lloyds Banking Group, have mastered the art of job sharing, proving that two heads can indeed be better than one. Join us to learn about the unique partnership they’ve built over nine years, sharing insights into how combining different strengths and perspectives leads to superior outcomes. Tune in for a conversation that challenges conventional leadership norms and offers a refreshing perspective on ambition and success.

Episode Timeline:

00:00 Introduction

​​08:41 Supporting each other and managing priorities

17:49 The benefits of two coaches for a team

24:10 How to play to each other's strengths

32:07 Why creating a work-life balance is so important

47:42 Communication practises for effective teamwork

56:39 Flexible working enhances productivity and satisfaction

Key Takeaways:

• Clare and Annabelle highlight how their contrasting personalities and skills enhance decision-making and problem-solving. They emphasise that two heads can indeed be better than one, providing richer ideas and solutions, which in turn benefits the entire team and organisation.

• The conversation addresses common misconceptions about job sharing, such as it being more work for managers or only suitable for certain roles. Clare and Annabelle debunk these myths by sharing their experience of managing each other’s development and workload, easing the burden on their line manager.

• On a personal level, job sharing has allowed Clare and Annabelle to maintain a healthy work-life balance. They can pursue personal interests and family commitments while still having fulfilling careers.

ABOUT Clare Freshwater-Turner & Annabelle Richards

Annabelle and Clare are a jobshare and senior managers in Sustainable Business at Lloyds Banking Group, working in the Nature team. They have been with Lloyds Banking Group for many years, working in a wide variety of roles in the Finance and Sustainability functions. These included leading teams, culture change and developing manager training programs. They joined the Group Sustainable Business Team in 2022 supporting Dr. Rebecca Heaton in setting up the team. After they both completed the CISL course with a distinction, they transferred to the nature senior manager role. Within the Nature team, their primary focus is to integrate nature into decision-making and developing training to meet business unit requirements.

Connect with Annabelle & Clare:

Website: https://thejobsharecoach.com/

LinkedIn: https://www.linkedin.com/company/thejobsharecoach/

Connect: 


Find | Cathleen O’Sullivan

Business: cathleenmerkel.com

Email: cmc@cathleenmerkelcoaching.com

LinkedIn: https://www.linkedin.com/in/cathleen-merkel/

Instagram: https://www.instagram.com/legendary_leaders_cathleenos/

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Are you merely enduring tough times, or are you truly thriving through them? In this episode of Legendary Leaders, army veteran and leadership expert Rachel McGill joins Cathleen to explore the nuanced art of resilience. Rachel unveils the clear difference between merely bouncing back and proactively moving forward. She shares her journey, from breaking a world record to creating Resilient Leaders Elements, a framework designed to help leaders like you build genuine resilience. Discover why true resilience is not about muscling through challenges but about adapting, making better decisions under pressure, and balancing control with adaptability. Tune in for a conversation that will inspire you to transform challenges into opportunities and rethink the way you lead during challenging times.

Episode Timeline:

00:00 Introduction

05:40 How to best structure your day and maximise energy

12:17 Building and developing resilient leadership skill

20:26 Why inclusion is a fundamental need

34:04 Turning crisis into opportunity

41:10 Visualising desired outcomes helps build resilience

51:12 Foreseeing crises, staying informed and being prepared

01:08:51 Authentic leadership and emotional intelligence

01:15:32 True diversity requires different perspectives and experiences

Key Takeaways:

• Rachel explains that resilience isn't about simply toughing it out through difficult times. She explains how having a bias for achievement and a positive intention can provide clarity and direction even during uncertainty.

• Cathleen and Rachel discuss the importance of creating a culture where everyone feels included and empowered to lead. This involves sharing control, encouraging openness, and fostering an environment of trust and accountability.

• Rachel shares stories of experience in the army and in business, emphasising the need for leaders to be adaptable and aware of their environments. During times of crisis or change, the ability to reassess and invite diverse perspectives becomes crucial.

ABOUT Rachel McGill

Having served as an army officer, Rachel McGill has 30 years’’ leadership development experience and specialises in the development of resilience in leaders and the tools they need to succeed. As co-founder of Resilient Leaders Elements with her colleague Dr Jeremy Mead, her ambition is to make world-class resilient leadership development available to all. Rachel has designed and facilitated hundreds of courses for thousands of people and leads on ensuring pragmatic approaches to leadership development.

Connect with Rachel McGill:

Website: www.resilientleaderselements.com

X: www.twitter.com/leaderselements

Facebook: www.facebook.com/resilientleaderselements

Instagram: www.instagram.com/resilientleaderselements

LinkedIn: https://www.linkedin.com/company/resilient-leaders-elements

Connect: 


Find | Cathleen O’Sullivan

Business: cathleenmerkel.com

Email: cmc@cathleenmerkelcoaching.com

LinkedIn: https://www.linkedin.com/in/cathleen-merkel/

Instagram: https://www.instagram.com/legendary_leaders_cathleenos/

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What if you stopped waiting for the right time and started living fully right now? In this episode of Legendary Leaders, Cathleen O'Sullivan welcomes the inspiring Keisha Hickson, a transformative thought leader and resilience advocate. Diagnosed with a rare incurable cancer multiple myeloma at a young age. Keisha's story isn't just about survival; it's about thriving and leaving a legacy on her own terms. She explores her experiences of overcoming fears and embracing authenticity daily, all while battling a rare incurable disease. Keisha also shares her insights on ‘daring to change’ and how to make bold changes and decisions. Tune in for a conversation that will challenge you to start living now and inspire you to create your own legendary legacy, one step at a time.

Episode Timeline:

00:00 Introduction

08:22 Keisha's life-changing cancer diagnosis

18:00 Normalising diverse paths to impact by addressing struggles

26:19 How to support employees with invisible disabilities

38:08 Discovering your "Why" is crucial in defining your legacy

50:57 Celebrate milestones, embrace resilience, and pursue true passions

57:57 Being a proactive advocate for healthcare

Key Takeaways:

• Keisha emphasises the importance of determination, action, resiliency, and execution through her concept of "Dare to Change." She explains how she moved from a place of complacency to making bold changes and decisions.

• Keisha shares the challenges of living with an invisible disability, such as her ongoing battle with multiple myeloma. She explains how she manages her condition while maintaining her daily activities and endeavours.

• Cathleen and Keish talk about leaving a legacy that is not defined solely by financial success but rather by the impact on our community, loved ones, and personal fulfilment.

ABOUT Keisha Hickson

Keisha Hickson is a professional speaker, transformative thought leader, and passionate advocate for resilience, transformation, and women’s empowerment. Her personal journey, marked by a diagnosis of multiple myeloma and a challenging prognosis, has fueled her pursuit of a limitless legacy. This concept, which she passionately advocates, is about living life on your own terms, creating a narrative that leaves a lasting and meaningful impact beyond conventional boundaries.

Keisha brings 25 years of experience in the financial industry to the table, including roles up to Vice President & Senior Branch Manager in Wealth Management. She has successfully owned and operated multiple businesses, demonstrating her diverse interests and business savvy. Her ventures include a children’s salon, a wellness brand, and a luxury gifting business, each flourishing under her leadership with collective revenues in the seven-figure range.

Connect with Keisha Hickson:

Instagram: https://www.instagram.com/thereal_keishahickson/

LinkedIn: https://www.linkedin.com/in/keisha-hickson/

Email: hello@keishahickson.com

Connect: 


Find | Cathleen O’Sullivan

Business: cathleenmerkel.com

Email: cmc@cathleenmerkelcoaching.com

LinkedIn: https://www.linkedin.com/in/cathleen-merkel/

Instagram: https://www.instagram.com/legendary_leaders_cathleenos/

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Are you still chasing the wrong kind of success? In this episode of Legendary Leaders, Nancy Ho joins host Cathleen O'Sullivan to discuss the hidden struggles of high-performing professionals and the paradox of success. Nancy shares how defining success externally can lead to a void of stress and unfulfillment. She talks about turning pain into gain, redefining what you truly want, and the importance of being authentic rather than conforming to societal pressures. Discover how your thoughts shape your reality and the power of self-reflection in transforming your life. Tune in for a conversation that invites you to redefine success on your own terms and move towards a life filled with genuine satisfaction and freedom.

Episode Timeline:

00:00 Introduction

08:40 Choosing what you want over what you need

17:22 The difference between authentic self-care and social pressure

27:37 Addressing your needs genuinely and fostering long-term relationships

36:32 Gradually changing bad habits to good ones with ongoing support and strategy adjustments

44:28 Success comes from the inside so focus on inner fulfilment

50:05 Living in the past and having a fear of judgment

01:01:01 Wake up calls from life

Key Takeaways:

• Nancy emphasises the importance of self-reflection to understand your own habits and tendencies. Being aware of the pain points and reflecting on them helps to make necessary changes.

• Nancy explains that recognising the authentic pain (what one truly wishes to avoid) and the real gain (the genuine pleasure and outcome desired) can lead to more motivated and effective action.

• Cathleen and Nancy discuss how true motivation and contentment come from internal desires rather than external validation. Nancy highlights the importance of doing things for yourself rather than seeking approval from others.

ABOUT Nancy Ho

Introducing Nancy Ho, a distinguished Life Strategist, Clarity Messenger, and state-of-mind specialist with over 26 years of experience guiding individuals toward holistic success. Throughout her illustrious career, Nancy has empowered over 10,000 clients, including C-Suite executives, mid-level managers, and business owners, to navigate the intricate balance between professional achievement and personal fulfillment. As an internationally-recognized thought leader on "The Professional Paradox," Nancy brings a unique perspective to the podcasting world. With a focus on helping high-performing professionals transcend the silent weight of success, Nancy's insights offer valuable guidance for listeners seeking harmony in their professional and personal lives. Nancy's expertise lies in addressing the disconnect between external success and inner fulfillment. Her comprehensive approach includes personalized executive coaching, strategic planning, and confidential support tailored to the unique needs of each client.

Connect with Nancy Ho:

Website: https://www.nancyho.net/

LinkedIn: https://www.linkedin.com/in/nancy-ho-exec-coach/

Instagram: https://www.instagram.com/lifecoachnancyho/

Connect: 


Find | Cathleen O’Sullivan

Business: cathleenmerkel.com

Email: cmc@cathleenmerkelcoaching.com

LinkedIn: https://www.linkedin.com/in/cathleen-merkel/

Instagram: https://www.instagram.com/legendary_leaders_cathleenos/

FOLLOW LEGENDARY LEADERS ON APPLE, SPOTIFY OR WHEREVER YOU LISTEN TO YOUR PODCASTS.