Michael Contento is the Founder & Chief Growth Strategist at Simple Mystery, a strategic advisory firm helping business owners, founders, and leadership teams design and execute powerful exit strategies that unlock long-term growth.

After three decades of building, scaling, and exiting companies across technology, healthcare, hospitality, and real estate, Michael discovered a simple truth:
an exit strategy isn’t the end of your story, it’s the foundation of your growth strategy.

Before launching Simple Mystery, Michael served as Managing Partner at F12.net, leading Corporate Development and M&A Strategy. During his tenure, he helped shape F12’s acquisition roadmap and successfully integrate multiple high-impact deals, including the acquisition of his own MSP, My Blue Umbrella, which he founded in 1996 and scaled into one of Canada’s most respected technology providers.

Beyond technology, Michael has founded and invested in ventures spanning Contento Capital (investment), Community Choice Pharmacy & Aivora (healthcare), Fresh Leap, a multi-brand restaurant group featuring Second Cup, Freshii, and Noodle Box, and Gothic Trends (real estate).

In 2020, Michael authored the Amazon best-seller The Bottom Line: What You Need for Success in Business, Leadership, and Life, and is currently developing his second book, exploring the intersection of AI, leadership, and generational growth.

Today, through Simple Mystery and his broader ecosystem, Michael helps founders and CEOs prepare their companies, and themselves, for successful transitions that drive wealth, legacy, and freedom.



Simple Mystery

Org chart

Teams

Offices

Similar companies