Gregory Cleary
Founder, Pinnacle Business Guides
Bio Info
Greg Cleary is an entrepreneur, business advisor, author, and founder of Pinnacle Business Guides, a growing community of accomplished business leaders who help entrepreneurial leadership teams build stronger companies—and better lives.
Greg has spent his career studying what separates businesses that simply grow from those that become truly exceptional. Rather than approaching leadership from theory, his perspective has been shaped by decades in the field: building businesses, coaching leadership teams, facilitating thousands of workshops, developing high-performing advisors, and helping entrepreneurs navigate the very real challenges of growth, people, execution, sales, and leadership.
In 2010, Greg became one of the earliest Certified EOS Implementers®. He went on to personally implement EOS with 149 companies in the Twin Cities and became the #1 EOS Implementer based on sessions conducted and revenue generated before ultimately leaving the community to build what he believed business leaders needed next.
That experience became an important catalyst for Pinnacle Business Guides. Greg saw that successful entrepreneurial companies often needed more than a single prescribed methodology. They needed proven principles combined with a deeper, more flexible set of tools for strategy, people, sales, profitability, leadership development, and execution. Pinnacle was built around that belief: give exceptional leaders battle-tested tools and principles while preserving the judgment, flexibility, and individuality that great advisors bring to the table.
Greg is also the architect of Sales Mastery, his practical approach to business development and client creation. His experience includes conducting more than 6,000 workshops, and his Sales Mastery programs have been used by hundreds of business Guides and Implementers to build confidence, improve their sales process, and create thriving advisory practices. His philosophy is distinctly practical: no theory for theory’s sake—focus on the conversations, systems, behaviors, and relationships that actually produce results.
Today, Greg’s work sits at the intersection of entrepreneurship, leadership, business growth, sales psychology, executive transition, and the future of business advisory. He is particularly passionate about helping accomplished leaders recognize that the next chapter of their careers doesn’t have to mean slowing down. It can mean using decades of hard-won experience to create greater impact, more freedom, and work that is deeply meaningful.
His guiding philosophy is simple:
“Stop the grind and enjoy the climb.”
Publications
Peak Performance: The Five Principles Every Great Business Lives
The Path to the Pinnacle: Using Customized Business Operating Systems to Drive Growth
Enjoy the Climb: The Simple and Complete Guide to the Pinnacle Business Operating System
Previous Interviews
Success Leaves Clues
Gregory Cleary Reveals 40+ Years of Coaching Wisdom
Business Velocity - The Five Facets of Business™ Podcast
'Find Your "A" Players!' with Greg Cleary
Hire Power Radio Show
Attract A-Players & Avoid the Dunning-Kruger Hiring Trap with Greg Cleary
Creative Agency Success Show
Business Coaching, Staying Relevant, Achieving Success: Insight from Pinnacle Business Guides Founder Greg Cleary
Topic Suggestions
Why the Best Business Leaders Never Climb Alone
The central idea behind Greg's forthcoming book: why the most successful CEOs surround themselves with guides, and why going it alone is the most expensive decision a leader can make.
Beyond the Operating System: When a Framework Stops Fitting Your Company
As one of the original EOS Implementers who left to build something more customized, Greg can speak candidly about where rigid business operating systems help, where they break down, and what leaders should do about it.
People, Purpose, Playbooks, Performance, Profits: The Five Pinnacle Principles
The framework Greg built from 149 company implementations, and how leadership teams use it to create clarity, accountability, and scalable growth.
Every Hero Needs a Guide: Why the Best Business Leaders Never Climb Alone.
What the next chapter looks like for experienced executives who want to guide others
Building a Leadership Team That Actually Executes
Why most accountability systems fail, how to get the right people in the right seats, and what changes when a leadership team finally aligns.
Enjoy the Climb: Why Growth Should Not Feel Like a Grind
Greg's counter-cultural take on scaling: the founders who burn out, the ones who don't, and what separates them.
The Next Chapter: Becoming a Guide After a Career of Leading
For executives, consultants, and coaches weighing what comes next, what it actually takes to build a practice guiding leadership teams.
The Coach's Blind Spot: Why Advisors Need Guides Too
Greg on what he learned building a community of elite Guides, and why the people advising leaders need support structures of their own.
Book Speaker Now
Click the button below to reach out to us and let us know!
2 Extra Reasons To Book...
Expert Guests Matter
Our guests have experience appearing on podcasts, so you don't need to coach them.
Eager to Share
Our guests see the value in appearing on your show, and they are ready to share their experience with their audience - and the world!