Key Highlights from Our Conversation:

From Singer to Startup Founder 

Michael's entrepreneurial journey began unexpectedly when allergic reactions to his cat ended his singing career. This random life disruption pushed him to explore new paths, eventually leading him to tech and startups. His story is a powerful reminder that sometimes our greatest pivots come from unexpected places.

The Portuguese Beach Crisis 

After leaving his position at unicorn startup Hopin, selling everything in Toronto, and moving to Amsterdam to build his AI coaching platform, Michael faced a devastating setback. His technical co-founder quit, the business model wasn't working, and he found himself on a beach in Portugal wondering what happened to his life. This raw, unfiltered look at founder rock-bottom moments offers rare insight into the emotional reality behind startup struggles.

Freedom as the Ultimate North Star 

In his darkest moment, Michael reconnected with his deepest motivation for entrepreneurship: freedom. With a cigar in hand and whiskey nearby, he realized that through all his ventures, what drove him was the freedom to make his own decisions, choose who to work with, and live life on his terms. This clarity became his compass, even guiding him away from fundraising when it threatened his core value.

The Life Partner Advantage 

While conventional wisdom often warns against mixing romantic relationships and business, Michael credits building his current startup with his wife as a key resilience factor. Their shared vision and values created a foundation of support through the toughest challenges, proving that with the right partner, entrepreneurial setbacks become more manageable because "we are doing it together."

The Matriarchal Wisdom Revolution 

Perhaps the most transformative insight came from Michael's wife, who offered a completely different framework for approaching competition: "You can win without making others lose." This perspective shifted Michael from wanting to dominate competitors to seeing them as market validation partners, using a beautiful winemaker analogy – different wines serve different preferences, but all winemakers help build the market together.

The Calendar Discipline 

Michael maintains strict hour-by-hour planning to perform at his peak. Rather than restricting freedom, this structure creates the space for what matters most. He knows his optimal start time (8:00 AM, not 5:00 AM), blocks non-negotiable time for his dog, and maintains focus during work hours. This personalized routine enables the very freedom he values most.

Breaking the Founder Loneliness Loop 

For founders without a built-in support system, Michael emphasizes deliberately building relationships with other entrepreneurs. Sometimes this means reaching out at 2 AM to discuss challenges with trusted peers. The key is finding specific individuals with whom you can be completely vulnerable, rather than trying to open up in large group settings.

My Personal Reflections:

Michael and I share a lot in common. We are both embracing a nomadic lifestyle at the moment, but most especially, we are both united in deep relationships with our respective partners. I often get asked myself what has been the key to my resilience and growth over the years, and I always reply that even before meditation, my real inspiration and support system has been my now wife. I've learned how to see life through different eyes—the eyes of a woman who consciously and unconsciously makes you reflect on all your biases and, yes, very often your toxic masculinity too! Doing business the right way, the sustainable and long-term way, has a lot to learn from women in my opinion, and I wish everyone could learn this soon enough in their career and life.