One of my favorite parts of hosting The Strategic Business Influencer is the chance to sit down with leaders who have lived through the highs and lows of entrepreneurship—and are honest enough to share the lessons they’ve learned along the way.
In a recent episode, I had the privilege of interviewing David Chavez, founder and CEO of Assured Strategy. David is a military veteran, former CPA, serial entrepreneur, and Scaling Up coach who has advised hundreds of CEOs across the world. He’s taken five companies public during his time at Arthur Andersen, built and sold his own CPA firm, and coached over 280 businesses through growth and exits.
What makes David’s story so powerful is that he’s not just teaching frameworks. He’s walked the path himself—making mistakes, learning what not to do, and building the kind of credibility that only comes from experience.
Lessons in Leadership and Growth
When I asked David what shaped his leadership most, he pointed to the discipline he gained from the Army. Contrary to common perception, the military didn’t just teach him structure—it gave him invaluable training in leadership and how to improve himself. That foundation helped him navigate later challenges in corporate life and entrepreneurship.
David was also candid about learning from failure. He shared that some of his most important lessons came from moments where he “botched leadership”—losing key people or missing objectives. Those painful experiences became turning points in how he approached leading teams and scaling businesses.
Why Humility Matters
One of David’s strongest messages for CEOs is the importance of humility. Confidence may help get a company off the ground, but unchecked ego can stall growth. He looks for humility in every client he coaches, knowing that it’s the leaders willing to listen, learn, and admit mistakes who ultimately succeed.
Scaling Beyond the Founder
Like many entrepreneurs, David hit a wall when his CPA firm stopped growing. He realized his need for control was holding the company back. Reading Mastering the Rockefeller Habits introduced him to the Scaling Up framework, which helped him see that strategy—not just execution—was the missing piece. That insight has since shaped his entire approach as a coach.
Redefining Freedom
Today, through Assured Strategy, David helps leaders align their teams, sharpen execution, and scale with clarity. But at the heart of his work is a bigger goal: helping leaders define and find their version of freedom.
For David, freedom means spending less time stuck in operations and more time with clients, listening, solving problems, and innovating. He encourages every leader to define what freedom looks like for them—and to intentionally build their business in a way that makes it possible.
Why This Conversation Matters
David’s story is a reminder that scaling a business isn’t just about numbers and systems. It’s about discipline, humility, and the willingness to evolve as a leader. His perspective shows that the journey from founder to CEO is less about holding on—and more about letting go.
If you’re a founder or executive navigating growth, I know you’ll take away practical insights and a fresh perspective from this episode.
Want to learn more about David and the incredible work his team is doing? Visit AssuredStrategy.com.
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