In this episode, Matt sits down with Cole Snell, a serial entrepreneur with over two decades of experience building and exiting ventures across food, insurance, blockchain, and private credit. Now on a mission to revolutionize SMB loans with an AI-driven, blockchain-enabled credit engine, Cole shares his take on leadership, company culture, and the power of self-awareness.

From learning hard lessons about trusting his team and planning for his own exit, to discovering the impact of setting the right example—from the boardroom to the bar—Cole shares the pivotal moments and stories that shaped his approach to building businesses meant to outlast him.

Key Topics Discussed:

• Building Companies with an Exit in Mind
• Implementing Superpower Culture
• Founder Self-Awareness and Succession
• Learning from Past Exits and Board Dynamics
• Leadership Lessons from the Food Industry
• Harnessing AI and Expanding Founder Bandwidth

Welcome to the debut episode of If They Knew What I Know, where we dive deep into the untold stories and invaluable lessons of experienced business leaders. In this episode, Matt sits down with fellow entrepreneur Erin Gregor to unravel the transformative journey from building his first business with his father, to navigating failures, and finally creating a thriving second venture focused on leadership, knowledge transfer, and business continuity. Listeners will hear firsthand how personal challenges—including a health scare during the pandemic—sparked the insight that true business resilience comes from capturing the unique, often undocumented knowledge held by leaders.

They discuss why traditional SOPs and systems fall short, and how his innovative approach—what Matt calls "the genius handoff"—helps owners prepare their organizations for succession, sale, or simply stepping back, all without missing a beat. They also talk about practical examples, hard-won lessons, and the realities and misconceptions of entrepreneurship, leadership succession, and building businesses that endure. Be sure to subscribe on your favorite podcast player for new episodes!

And to learn more about COtingency, visit: www.COtingency.com

Key Topics Discussed:

• The Inspiration and Lessons from Past Businesses:
• The Critical Shift from Growth to Exit Planning:
• What Typical SOPs Miss in Succession and Knowledge Transfer:
• Misconceptions Business Owners Hold About Replacements and Documentation:
• How Leaders and Buyers Use Structured Knowledge Extraction:
• The Importance of Timing, Scale, and Proactive Preparation: