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E225 | Invest In Your Leaders with Cameron Herold, The CEO Whisperer 

Leadership development is not about studying leadership, but about practising leadership in an intentional way, in a culture and environment that enables learning. 

For over 20 years, Cameron Herold has been the mastermind behind hundreds of companies’ exponential growth. His passion for coaching and mentoring others earned him the reputation of The CEO Whisperer

His career in business coaching started with College Pro Painters, a house painting franchise he joined at the age of 21. This franchise was the perfect breeding ground for an entire generation of entrepreneurs and businesses.

By the age of 35, Cameron had built his first two $100m companies, and in just six years of being the COO for 1-800-GOT-JUNK? he transformed it into one of the most successful new business ventures of the last decade, with a spectacular growth from $2m to $106m in revenue.

In 2016 he founded the COO Alliance with one simple goal in mind: to provide COOs with the same professional development and growth opportunities CEOs have enjoyed for many years.

In this episode, Cameron shares how he discovered his passion for mentoring leaders, his beginnings in the College Pro Painters franchise, and the strategies CEOs should use to achieve alignment in their organisations.

We also dive in and talk about his five books, a truly powerful resource on leadership and growth solutions for companies. 

In today’s episode:

  • Where it all started- The College Pro Painters franchise
  • Nurturing tomorrow’s business leaders
  • Build real teams and achieve company alignment
  • 1-800-GOT-JUNK?
  • What’s the difference between a CEO and a COO
  • Cameron’s books
  • Living a nomad life


The first-ever network for COOs in the world

COO Alliance was born in 2016 when Cameron realised that despite the abundance of peer groups and training courses on the market, there were none for Chief Operating Officers.

Having played the role of second in command a few different times in his career, Cameron was perfectly aware of how important it was to have access to good learning platforms that could enable a COO to develop his leadership skills.

“There are so many amazing groups and organisations for entrepreneurs, and then there are all kinds of organisations for marketers and lawyers and engineers. But there’s never been that organisation for a COO or a second in command.”

Where it all started

Cameron Herold was destined to become an entrepreneur. At just 21 years old, after joining a franchise organisation, he started running his own house painting business, which turned out to be the perfect ramp for his career. At the age of 24, he was already appointed general manager of the company and was responsible for hiring and recruiting over 9000 people yearly. But the journey was not an easy one.

“Every year, we had to go out and recruit, hire, and train 800 franchisees, and then in one month, we had to train those 800 people to hire 8,000 painters. It was very hard. We produced 64 million in painting in four months, and then 8,800 kids would quit and go back to university, 60 of us would get drunk, and then the next day, we would do it again. “

Cameron says this business model was good because it made him understand how to simplify a business back to its core elements.

Nurturing tomorrow’s business leaders

In 1990, when the idea of business coaching was just starting to take shape, Cameron was already in charge of growing and instructing 120 franchisees and business entrepreneurs.

During that time, Cameron discovered his passion for coaching and leading others, which later earned him the reputation of The CEO Whisperer. The true aim of College Pro Painters was to grow entrepreneurs, and many of the college kids that worked in that franchise became famous business leaders.

“We used to call ourselves the real world MBA, and College Pro Painters became the breeding ground for almost a dozen other companies and for the leadership of all of those brands”, says Cameron.

When Elon Musk and his brother, Kimbal, were starting their first company, Zip2, they used Cameron’s name as a reference and managed to get the funding they needed.

”They wouldn’t back Elon. His vision was too big, and he was way out of the box. So they approved their funding solely on the experience that Kimbal gained while working for College Pro Painters”, says Cameron. In 1999, the two brothers sold Zip2 to Compaq for almost $350 million.

Building real teams 

Building a successful team is more than just finding a group of people with the right mix of professional skills. It’s about helping those people find common ground. 

In a company with multiple sectors and teams, everybody needs to focus on the good of the company.

“You need to get those leaders to realise that when they’re coming into a meeting and they’re arguing and debating, they’re not arguing for their area; they’re arguing what’s best for the company.” According to Cameron, if we can get leaders to function in alignment and understand that their role is to create consensus and growth, then we’ll start to see a “supercharge of the organisation.” 

How can companies achieve alignment?

When people are aligned with your company’s goals, they feel like they are a key part of your success. This can be the difference between a profitable business and a failed venture. In Cameron’s opinion, four strategies really help align an organisation: 

The first one revolves around the concept of Vivid Vision, which he covered in some of his books. This method helps companies bring their ideas together to generate a clear plan for their future.

The second strategy is a deep alignment with core values. The idea behind this strategy is to choose your employees in accordance with your company’s culture.

The third strategy refers to the concept of BHAG, described by Jim Collins in his book Built to Last, which refers to creating a long-term goal that everybody in the company can rally behind. 

The fourth strategy concentrates on your own core values. Cameron’s core value is helping entrepreneurs achieve their dreams, and he’s doing that through his books, his COO Alliance, his Second in Command Podcast and his Invest In Your Leaders course.

Living the nomad life

Right before Covid started, Cameron and his wife decided to abandon the lifestyle they were accustomed to and start travelling the world. They sold everything they had: cars, houses and furniture, and embarked on a global adventure. In 4.5 years, they visited 33 countries and don’t plan to stop anytime soon.

“We just decided to purge. We got rid of all of our houses, all of our cars, sold all of our furniture, and she got rid of all of her Jimmy Choos and Louis Vuittons’. And then my wife, pre-Covid, wanted to start travellingSo yeah, I own three pairs of shoes. They’re all sitting within four feet of me, got a backpack and a day pack, and it’s very freeing. We just travel full time.”

They share all of their adventures, raw and unfiltered on their Youtube travel channel, Ever Wander.

Book recommendations:

Vivid Vision: A Remarkable Tool For Aligning Your Business Around a Shared Vision of the Future

Double Double: How to Double Your Revenue and Profit in 3 Years or Less

The Miracle Morning for Entrepreneurs: Elevate Your SELF to Elevate Your BUSINESS

Meetings Suck: Turning One of the Most Loathed Elements of Business into One of the Most Valuable

Free PR: How to Get Chased By The Press Without Hiring a PR Firm

Patrick Lencioni- The Five Dysfunctions of a Team: A Leadership Fable, 20th Anniversary Edition

Gregory David Roberts- Shantaram: A Novel

Alfred Lansing & Nathaniel Philbrick- Endurance

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