Bill Whitehead

Leading Financial Advisor Entrepreneur



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Bill Whitehead has been a successful entrepreneur for over thirty years. He has had a rich professional journey marked by resilience, tenacity, and a relentless pursuit of excellence in both business and personal endeavors. As a coach, he works with his clients to inspire and empower them to overcome obstacles, hold them accountable to reaching their goals, and Make BIG Happen.

Hailing from Northern Ontario, Canada, Bill’s passion and exceptional talent in hockey earned him a scholarship to Union College in the United States. However, knee issues forced him to pivot from his athletic aspirations, prompting his return to Canada.

Undeterred by setbacks, Bill pursued higher education and obtained his Honors Business Degree from a college in Canada, laying the foundation for his future entrepreneurial ventures.

Business Highlights:

  • At 22, Bill opened an award-winning restaurant franchise and ran it as the operating partner. He was able to open the restaurant thanks to the unwavering belief of his mother, who extended financial assistance by taking a second mortgage on her home. This bold leap led Bill to a successful exit eight years later.
  • Subsequently, Bill’s expertise caught the attention of a prominent hotel owner, who recruited him as Chief Operating Officer (COO). His tenure saw him overseeing operations and driving strategic initiatives for a portfolio of hotels for about two years.
  • Switching fields, Bill became one of Canada’s leading financial advisor entrepreneurs. Over 18 years, he recruited and trained a team that propelled his office to become the #1 destination for financial advisory services in Ontario. He sold this business in stages as it had grown to over $2 billion in assets.
  • Bill has been involved in numerous other successful start-up businesses over the past three decades in addition to real estate opportunities.

Personal Highlights:

A strong, dependable leader who loves coaching others to success, Bill coached Minor League Hockey for eight years in addition to Special Olympics Floor Hockey. His other interests include snowboarding, golf, and extreme skiing. Ever the visionary, he harbors a curiosity for the future and eagerly anticipates advancements such as flying cars.

Bill’s enduring marriage of 38 years to his wife, Debbie, stands as a testament to their unwavering commitment and shared values. Together, they have raised three children, embodying the importance of family and unity.

Featured Podcast:

Listen to Bill Whitehead’s podcast episode – Finance Entrepreneur Uses These 4 Insights To Supercharge Sales Teams

CEO Coaching International

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CEO Coaching International works with CEOs and their leadership teams to achieve extraordinary results quarter after quarter, year after year. Known globally for its success in coaching growth-focused entrepreneurs to meaningful exits, CEO Coaching International will Make BIG Happen for you and your organization. The coaches at CEO Coaching International are former CEOs, presidents, or executives who have led profit growth in businesses ranging in size from startups to over $10 billion. Many have led their companies through successful eight, nine and ten-figure exits.