RadEO is a podcast for Entrepreneurs by Entrepreneurs, hosted by Ross Drakes and occasionally Rich Mulholland. Since 2018, we’ve released 50+ episodes featuring EO members worldwide, sharing their journeys and lessons learned.
Produced by Entrepreneurs Organisation South Africa, RadEO airs every two weeks, bringing you insights from business owners on building and sustaining their ventures.
Learn more about EO at eonetwork.org. If you’re an EO member with a story to share, get in touch!

Hello and welcome to RadEO a podcast by Entrepreneurs for Entrepreneurs. It is hosted by Ross Drakes. In this podcast, we share the stories of EO entrepreneurs, their personal stories, some insight into their entrepreneurial journey and the lessons from how they think about their business today.
What if the way you lead is the very thing holding your business back?
In this episode of RadEO, Ross sits down with Joss Du Trevou, a leadership coach who has spent years helping high-performing entrepreneurs, CEOs, and teams get out of their own way.
Joss believes that most business problems aren’t external; they’re internal. Your fears, mindset, and habits shape how you show up as a leader. If you’re not paying attention, they might be the biggest bottleneck in your business.
Key Takeaways:
Your leadership sets the ceiling for your business growth.
Most leaders are blind to their own weaknesses.
You don’t need all the answers.
We get into self-sabotage, imposter syndrome, the power of coaching, and why ego is the silent killer of business growth.
If you’re a founder, CEO, or just someone trying to figure out how to lead better, this episode will change your thoughts about leadership.
Subscribe on iTunes, Spotify or Overcast. Enjoy.
More about Joss Du Trevou
Joss Du Trevou has been on both sides of leadership; running billion-rand corporate teams and scaling his own family business. Now, he helps entrepreneurs do what he had to learn the hard way: get out of their own way.
He grew Ecomotel from 3 to 6 branches, scaling revenue past R30 million while building a team that could run without him. Before that? 18 years in investment banking, leading teams at ABSA, Nedbank, and global banks, managing billions in corporate finance.
Now, as an ICF-accredited executive coach, EO mentor, and UCT Business School coach, he helps founders stop micromanaging, overworking, and getting stuck in the weeds so they can actually lead.
Because if your business falls apart the second you step back, you don’t own a business, you own a prison.

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Our favorite episodes

Hello and welcome to RadEO a podcast by Entrepreneurs for Entrepreneurs. It is hosted by Ross Drakes. In this podcast, we share the stories of EO entrepreneurs, their personal stories, some insight into their entrepreneurial journey and the lessons from how they think about their business today.
In this episode, we had an inspiring conversation about the value of thinking big, setting BHAGS (can’t wait for you to hear this one), and the importance of scaling. Our guest – Bill Gallagher is a highly-rated business coach who has led four companies from startup to more than $550 million in annual revenue
Be ready to be inspired by Bill’s unbelievable journey and how his goal of helping 5 million leaders worldwide drives his work.
My Key Takeaways:
Big Hairy Audacious Goals: Bill explains the importance of “BHAGs”, which help leaders think exponentially rather than incrementally. We talk about how BHAGs encourage a mindset shift.
Scaling as a Path to Impact: We talk about how scaling is about creating meaningful impact that extends beyond financial metrics. By focusing on creating value, companies will inspire not only their employees but investors and customers to share a vision – making scaling a powerful tool for change..
Exiting Businesses in the Growth Trajectory: The importance of timing your exit in the business world is understated. We elaborate about planning the exit during growth phases can maximise valuation
The Game of Business Should Be Fun: For Bill, leaders who treat business as a game are often more innovative, bringing fresh ideas to their companies.
Bill’s journey is truly incredible. From radio stations to tech startups, to coaching CEOs led him to realise that success comes from the impacts you leave. His 30 year BHAG of helping 5 million business leaders is the definition thinking big which drives his way of life. This episode is incredibly fascinating and great for anyone looking to take their business or personal growth to the next level.
Tune in every week for the insights
Subscribe on iTunes, Spotify or Overcast
More about Bill
Bill Gallagher is a highly rated business coach whose passion is helping CEOs and entrepreneurs manage growth better; restore time, order and sanity to their lives—and get growing again or growing faster. With more than 38 years of entrepreneurial and executive experience and 19 years coaching and training leaders who want to improve their leadership and performance, he now works with leaders and teams in over 28 cities and 13 countries. He has led four companies as CEO/owner and was a partner/executive in two others as they grew from startup to more than $550 million in annual revenue.
A former DJ and radio executive, Bill hosts the Scaling Up Podcast. In his free time, he is an avid surfer, sailor, skateboarder, pilot, scuba enthusiast and recovering triathlete. Happily married for 30 years, he and his wife Lori live in the Oakland Hills and are parents to two young adult entrepreneurs.


Hello and welcome to RadEO a podcast by Entrepreneurs for Entrepreneurs. It is hosted by Ross Drakes. In this podcast, we share the stories of EO entrepreneurs, their personal stories, some insight into their entrepreneurial journey and the lessons from how they think about their business today.
In this episode, we chat to Trent Clark, the CEO of Leadershipity – a growth coaching company that is dedicated to doubling organizations in half the time. He is also a three-time Major League Baseball World Series coach, who has fantastic leadership abilities – both on and off the field – with a unique blend of athletic discipline and entrepreneurial insight to his work.
My key takeaways:
The Importance of Team Culture
Trent explains how crucial a purpose-driven culture is to the success of an organization. He references Peter Drucker’s famous quote, “Culture eats strategy for breakfast,” when highlighting how the best strategies can fail without the right team culture.
The Value of a Coach
Trent draws parallels between coaching professional athletes and entrepreneurs and highlights the significance of having a coach in both instances; as top athletes have coaches that keep them aligned with their goals and entrepreneurs should have coaches to help them stay on track.
The Weight of the Ring
Trent emphasizes the responsibility and challenges that come with achieving significant success in leadership roles. The Weight of the Ring is a metaphor for the burden of maintaining momentum, managing increased expectations and guiding others to look up to you. Achieving great success isn't just about reaching the goal; it's about enduring the added pressures and growing to meet the demands that follow, turning challenges into opportunities for further growth.
Hyper-Learning in Tough Times
During economic downturns, Trent notes that successful entrepreneurs are often “hyper learners” who have the ability to adapt to changes quickly and emerge from challenges much stronger. The ability to adapt and strive to continuously learn new skills are the key to thriving in difficult times.
Trent Clark discusses the importance of strong team culture, the value of coaching, and the responsibilities that come with leadership and success in both sports and business. What really captured me was his “weight of the ring” metaphor and the message that true success involves embracing the challenges and the growth that comes from them.
Enjoy.
Tune in every week for the insights
Subscribe on iTunes, Spotify or Overcast
More about Trent:
Trent Clark is a three-time Major League Baseball World Series coach who has made significant contributions both on and off the field. With over 12 years in MLB, he played pivotal roles in leading teams to success, including the Cleveland Indians in the World Series in 1995 and 1997. Trent's expertise in strength and conditioning helped shape many athletes' careers during his tenure.
Beyond his baseball achievements, Trent is a successful entrepreneur and leadership coach. He is the CEO of Leadershipity, a consulting firm dedicated to developing exceptional leaders and sustainable organizational systems. His passion for empowering others has earned him the nickname ”Dream Maker,” reflecting his commitment to helping people achieve their goals and reach peak performance in both sports and business.


Hello and welcome to RadEO a podcast by Entrepreneurs for Entrepreneurs. It is hosted by Ross Drakes. In this podcast, we share the stories of EO entrepreneurs, their personal stories, some insight into their entrepreneurial journey and the lessons from how they think about their business today.
In this episode, we chat to Will Scott, a technology enthusiast, proud culture czar and hobbyist clubhouse builder, about overcoming setbacks and transforming challenges into opportunities, the power of belief and its impact on achieving personal goals and his strategy for maintaining motivation and turning adversity into triumphs.
My key takeaways:
Using Values to Drive Culture: Will explains the importance of having meaningful and clearly defined core values that employees can align with. He highlights the gap between having core values and actually embedding them into the company culture.
Embracing Flexibility gives you an edge: Will emphasizes the significance of embracing flexibility in modern workplaces and how the shift from traditional office setups to a more integrated approach allows individuals to blend their work and personal life seamlessly. Cultivating a culture that supports such flexibility could provide a substantial competitive edge for entrepreneurs and leaders alike.
Gratitude for Technology: Technology enables remote work possibilities. There are several key benefits that technology brings to the table: enhanced connectivity that allows teams to collaborate seamlessly across geographical boundaries, improved work-life balance where flexibility has benefitted individual employees which has contributed to higher job satisfaction and retention rates and embracing these technological advancements as catalysts for positive change.
Will’s ability to harness challenges as catalysts for growth left an indelible impression. What really captured me was his ability to distill complex experiences into actionable insights, making this episode a practical guide for navigating your teams challenges with courage and determination.
Enjoy.
Tune in every week for the insights
Subscribe on iTunes, Spotify, Google Podcasts or Overcast
More about Will:
Author of The Culture Fix and founder of The Culture Fix Academy, Will has helped hundreds of businesses fulfill their corporate culture dreams. He leads workshops and speaks regularly using his Alive, Thrive & Drive methodology and is host of The Culture Fix podcast. His 25-year span as an entrepreneur includes five start-ups, 2 exits and several Inc. 5000 appearances before focusing on Culture Fulfillment™ using his proprietary 9 deeds in 90 days. In 15 years as a member of EO Will has held several board positions and is ex-President of EO Wisconsin. He is a yoga devotee, avid traveller and loves everything outdoors.
