Matt welcomes Vijay Rajendran, a post-exit founder, venture builder at GAI Ventures, educator, and executive coach, for a discussion on leadership in the startup world. Vijay shares his journey of navigating through his first start-up to evolving into a CEO, discussing the significance of enabling others and the nuanced progression through different leadership stages. They talk about the importance of adaptability in delegation, understanding individual motivations at work, and building well-rounded teams with complementary strengths. Vijay also introduces frameworks like the 4 steps of delegation and discusses the working genius model to help leaders identify their areas of genius, competence, and frustration.

They also talk about the challenges and mindset shifts founders encounter, especially under pressure or after major transitions like an exit. Vijay shares his stories of processing uncertainty, avoiding hype, the primacy of building customer trust, and the evolving relationship with autonomy and burnout. He also advises founders to focus on talking to customers, building high-trust environments, and fostering strong communication. They also talk about the intersection of leadership, AI, and trust, and the necessity for companies to remain human-centric in their approaches, even as technology accelerates.

To learn more or connect with Vijay, visit: https://www.gai.ventures/

Key Topics Discussed:

• The Evolution of the CEO Role
• Lessons from Operating, Investing, and Coaching
• Startup Life Cycles and Founder Challenges
• AI’s Role in Modern Startups
• Trust and Communication in High-Performing Teams (and in AI)
• Intrinsic Motivation and Incentives Post-Exit

Matt welcomes Mike Lisovetsky, Co-Founder at Miro Advisory to discuss the realities of buying, building, and exiting businesses. Mike shares insights as a serial entrepreneur, having started companies from a young age and successfully navigating multiple exits. They discuss some of the ah-ha moments Mike has had as a founder and his role as a problem solver because dealing with problems is integral to the job. They also talk about the truth behind growing a business and building to exit versus being in a position where an exit is inevitable.

They discuss the nuances of transitions during exits, from knowledge transfer and SOPs to the emotional impact of selling a company. Mike talks about the challenges around transferring founder logic and judgment, sharing that even with documentation, much of the business’s unique value often resides in the founder’s head. They discuss trends in entrepreneurship through acquisition, the upcoming silver tsunami of retiring business owners, and the critical importance of finding the right buyer-seller alignment.

They also offer advice for aspiring entrepreneurs and those looking to build or sell, and what your next steps should be to maximize value and profit.

To find out more about Mike and connect with him, email him at:   📍 mike {at} mirroradvisory.com.

Key Topics Discussed:

• The Reality of Being a Founder
• Challenges with Knowledge Transfer in Exits
• Owner-Business Fit in Acquisitions
• Emotional Impact of Selling a Business
• Evolution in Business Sale Marketplaces
• Preparing for Acquisition or Sale

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: