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/

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

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/

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

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/

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