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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