If They Knew What I Know

Erin Gregor
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  • Entrepreneurship
  • Updated Semimonthly

If They Knew What I Know… is a podcast about what really happens when a business changes hands. Each week you’ll hear from owners who’ve sold, successors and buyers stepping in, and the experts who live inside deals and successions every day—M&A advisors, lawyers, estate planners, CPAs, operators, and more. Together they unpack the pitfalls, surprises, and smarter ways to prepare so that when it’s your turn to step back—or step up—you’re not guessing in the dark.

Episodes

  1. Jul 15

    Inside Business Acquisitions: Avoiding Mistakes and Maximizing Value

    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 FounderChallenges with Knowledge Transfer in ExitsOwner-Business Fit in AcquisitionsEmotional Impact of Selling a BusinessEvolution in Business Sale MarketplacesPreparing for Acquisition or Sale

    Inside Business Acquisitions: Avoiding Mistakes and Maximizing Value

  2. Jun 10

    Building to Exit: Designing Companies for Success and Smooth Transitions

    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 MindImplementing Superpower CultureFounder Self-Awareness and SuccessionLearning from Past Exits and Board DynamicsLeadership Lessons from the Food IndustryHarnessing AI and Expanding Founder Bandwidth

  3. May 6

    From Experience to Blueprint: Making Businesses Thrive Without You

    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: Top Six Topics DiscussedThe 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:

  • 3 Episodes

About

If They Knew What I Know… is a podcast about what really happens when a business changes hands. Each week you’ll hear from owners who’ve sold, successors and buyers stepping in, and the experts who live inside deals and successions every day—M&A advisors, lawyers, estate planners, CPAs, operators, and more. Together they unpack the pitfalls, surprises, and smarter ways to prepare so that when it’s your turn to step back—or step up—you’re not guessing in the dark.

Information

  • Creator
    Erin Gregor
  • Years Active
    2026
  • Episodes
    3
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Erin Gregor
  • Show Website
    If They Knew What I Know