From Architect to Technologist to Entrepreneur to Strategic Coach

The Journey

I trained as an architect at McGill University, which gave me something more valuable than design skills—a systems perspective. Architecture teaches you that problems often manifest far from their origins, like water in a basement that actually starts at the roof flashing. That thinking shaped everything that followed. I moved into digital product strategy with companies like Motorola and WebMD, then founded my own Lean/Agile software agency in 2003. I scaled that company to the Inc. 500 list for five consecutive years before successfully exiting via acquisition in 2013. That experience—building a leadership team, creating scalable operations, navigating due diligence, and managing the personal dimensions of transition—is what I bring to every client engagement today.

The Work

Today, I work as a strategic business coach, CEO coach, and exit planning advisor for founder-CEOs of companies in the $5M–$50M range. These are businesses past the startup phase but facing the challenges of true scale: leadership teams that aren't aligned, strategies that aren't differentiated, operations that depend too heavily on the founder. I help them break through growth plateaus, build leadership teams that can execute without them, and prepare for exits that maximize both valuation and personal readiness. My engagements range from three-day strategic planning intensives to year-long leadership team coaching to comprehensive exit preparation. The through-line is always the same: clarity, alignment, and execution.

The Approach

I don't deliver strategy decks that gather dust. I facilitate strategic planning retreats and sessions that produce decisions, priorities, and accountability. My "80% confidence" philosophy drives everything: pushing beyond 80% certainty on major decisions rarely justifies the delay, and strategy without implementation is just conversation. My Lean/Agile background means I favor iteration over rigid planning—quarterly priorities that respond to reality rather than five-year projections that become obsolete. And I believe the best strategies come from leadership teams who own the thinking, not consultants who hand down answers. My job is to ask better questions, create the conditions for honest conversation, and convert planning into quarterly roadmaps with clear ownership and measurable outcomes.

The Credentials

I've pursued certifications that complement operational experience with proven methodologies. My ScalingUp certification and Metronomics/3HAG training provide systematic frameworks for strategic planning and execution. Predictive Index certification adds behavioral assessment tools for optimizing leadership team composition and dynamics. Most recently, I earned my CEPA credential—Certified Exit Planning Advisor—which is the gold standard in exit planning education, awarded by the Exit Planning Institute. But credentials only matter if they're backed by experience. What I really bring is the perspective of having built, scaled, and sold a company myself. Most strategic consultants have studied exits; I've actually done one.

The Thought Leadership

I've hosted over 1,000 podcast episodes across shows including From Angel to Exit, Scaling Up Services, and Thinking Outside The Bud. I contribute regularly to Inc. Magazine, where I write about strategic planning, leadership development, and exit preparation. My forthcoming book, Springboard, challenges conventional exit planning wisdom—presenting a framework for using your exit as a launching pad rather than an endpoint, and addressing the reality that 75% of founders experience significant regret within a year of selling despite achieving financial success. I believe in sharing what I've learned, both the wins and the hard lessons.

Beyond Business

I'm a father of four children, ranging from elementary school to young adulthood. Parenting across such different stages is a daily reminder that different people need different things at different times—a principle that applies equally to the founder-CEOs I coach. I find clarity in nature: hiking, rock climbing, and backcountry skiing in remote places. I maintain a meditation practice and have been part of a long-term men's group focused on authentic connection, the kind of peer support every leader needs but few actually have. I'm not interested in helping founders build businesses that consume their lives. I help them build businesses worth running and worth buying—so they can live lives worth living.