Every founder reaches a moment when growth turns into legacy. Let’s make sure you’re ready when that moment arrives.

Philosophy & Approach

Michael's guiding philosophy: Never Quit. Always Move Forward, shapes everything he builds. It's not about avoiding failure or chasing perfection. It's about resilience, progress, and the discipline to keep building even when the path forward isn't clear.

At Simple Mystery, that philosophy translates into a simple commitment: help founders build companies that are ready for whatever comes next, whether that's growth, transition, sale, or succession. No shortcuts. No theory. Just clarity, discipline, and results.

Quick Facts

  • Founder & CEO: Simple Mystery

  • Certified Exit Planning Advisor (CEPA)

  • Founder of My Blue Umbrella (acquired by F12.net)

  • Founder of Community Choice Pharmacies

  • Founder of Fresh Leap (Second Cup, Freshii, Noodle Box, Chocolato)

  • Property Investor: Residential & Commercial assets across Canada & the U.S.

  • Author: The Bottom Line (Amazon Bestseller)

  • Philanthropy: Founder, Do Amazing Things Foundation

Never Quit.
Deliver Simplicity.

Because simplicity drives growth; and growth creates freedom.

Meet Michael Contento

Michael Contento brings over three decades of entrepreneurial leadership, innovation, and growth strategy to Simple Mystery.

A founder, operator, and advisor, Michael has built, scaled, and exited businesses across multiple industries, from technology and real estate to healthcare and hospitality.

Before launching Simple Mystery, Michael played a direct and pivotal role in the growth of F12.net, helping shape its M&A strategy and corporate development initiatives that accelerated national expansion.

His entrepreneurial journey began in 1996, when he founded My Blue Umbrella (MBU), a managed IT services company that grew into one of Canada’s leading MSPs before being acquired by F12.

Beyond technology, Michael’s portfolio includes founding and scaling Community Choice Pharmacies and multiple hospitality brands under the Fresh Leap banner, including Second Cup, Freshii, Noodle Box, and Chocolato.

In addition, Michael has built an extensive property investment portfolio across Canada and the United States, spanning both residential and commercial assets. This experience gives him firsthand insight into capital structure, cash flow optimization, and value creation across markets.

This diversity gives Michael a unique ability to see across industries, blending strategic insight with hands-on operational experience. He understands what it takes to build strong foundations, create transferable value, and prepare companies for lasting success.

“Every time I speak to a leader, I hear the same answers, the same ones I used to give myself. ‘I’m not ready yet. Maybe in a few years.’ But the truth is, getting ready starts long before the sale. It’s about strengthening the three legs of every successful exit: personal, financial, and business readiness.”

Michael is also the author of the Amazon bestseller “The Bottom Line: What You Need for Success in Business, Leadership, and Life,” and the founder of the charity “Do Amazing Things,” supporting new mothers and families striving for a better future.

Michael’s mission: to help founders design their growth and exit strategies with clarity, confidence, and purpose, transforming complexity into opportunity.