Michele Romanow on Disrupting the Status Quo, Unlocking Entrepreneurial Grit, and the Power of Rapid Execution
- Tony Chapman
- Oct 2
- 3 min read
Why Fearlessness and Speed Matter in Entrepreneurship
In this dynamic episode of Chatter That Matters, host Tony Chapman sits down with acclaimed entrepreneur, investor, and Dragon’s Den star Michele Romanow. Recorded live at Cannavision, Michele offers an unfiltered look into her journey founding seven diverse businesses before age 35, how she’s championing a new paradigm for venture funding at Clearco, and the tireless mindset it takes to lead innovation in Canada and beyond.
Romanow passionately challenges conventional wisdom about entrepreneurship, debunking the myth that game-changing businesses always start with massive ideas and perfect plans. “Most things start as little ideas,” she shares, emphasizing the need to dive in and iterate rapidly. Drawing from her own stories—whether building a sustainable campus coffee shop, pioneering caviar farming at 21, or reinventing founder financing—Romanow pulls back the curtain on the messy, exhilarating reality of turning dreams into action.
“Successful people do what unsuccessful people weren't willing to do,” Michele remarks, underscoring the vital roles of resilience, scrappiness, and humility in driving real-world results.
Building Iconic Businesses: Lessons from the Frontlines
Romanow reflects on the importance of surrounding yourself with the right people, both as co-founders and in mentorship. She offers concrete advice on finding partners, avoiding ego-driven pitfalls, and executing with urgency—often compressing “four days into one” through relentless prioritization and action. For aspiring entrepreneurs, Michele’s insights into overcoming perfectionism and embracing fast failure are both practical and empowering:
“You just have to force yourself to do it. It’s like a swimming pool—when you dive in, it’s never warm, but as soon as you’re in, you figure out how to tread water.”
Investing Beyond the Metrics: Why Stories and Grit Count
Tony and Michele also explore the evolution of investment models, including how Clearco’s data-driven approach levels the playing field for underrepresented founders. Still, Romanow is quick to point out the enduring power of stories, connectivity, and authenticity—qualities that make founders memorable to investors and customers alike.
She shares inspiring anecdotes of the impact her investments have made, from helping military veterans find financial freedom to backing women entrepreneurs escaping adversity. Her message? Behind every data point is a human story—and those narratives can catalyze meaningful change.
RBC and the Small Business Ecosystem
The episode concludes with insights from RBC’s Alan Depencier on the essential role small businesses play in Canada’s economy, touching on the support and solutions available for entrepreneurs at every stage of growth.
Takeaways for the Next Generation of Leaders
Speed is the startup’s superpower: Large companies move slow, so move four times faster.
Authenticity and resilience win: Founders with a personal mission, who can withstand setbacks, are unstoppable.
Storytelling creates traction: People remember your “why”—not just your numbers.
Listen now to discover why Michele Romanow believes “the less precious you are, the more successful you will be”—and how you can apply her hard-won wisdom to your own entrepreneurial journey.
About Chatter That Matters and Host Tony Chapman
Featuring insights for aspiring founders, entrepreneurs, and anyone craving inspiration with actionable strategies.
Chatter That Matters is one of Canada’s top-rated podcasts, showcasing stories and lessons from a diverse range of guests, including entrepreneurs, industry leaders, and everyday change-makers. Each episode illustrates how individuals transform challenges into triumphs through mindset and resilience.
Hosted by Tony Chapman—a renowned marketing strategist and three-time inductee into the Marketing Hall of Fame—this acclaimed show ranks among the top 0.5% of podcasts globally. Tune in weekly as Tony converses with guests who share invaluable wisdom on living a meaningful life.
🔥 Authentic voices. Remarkable journeys. Real strategies for success.
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