6x CEO Reveals the Brutal Reality of Scaling a Company
About this episode
Mike Grossman shares the emotional realities of scaling a company and the challenges faced by CEOs in the tech industry.
For more thoughts, clips, and updates, follow Avetis Antaplyan on Instagram: https://www.instagram.com/avetisantaplyan In this episode of The Tech Leader's Playbook, Avetis Antaplyan sits down with Mike Grossman, a six-time venture-backed CEO, longtime Silicon Valley operator, and author of Failure is an Option. With more than three decades of leadership experience inside high-growth technology companies, Mike offers a candid look at what startup life actually feels like behind the polished success stories. Rather than glamorizing entrepreneurship, Mike breaks down the emotional reality of leading companies through uncertainty, pressure, pivots, burnout, and unpredictable outcomes. He shares why resilience, grit, and emotional steadiness matter more than many founders realize, and why CEOs often feel isolated even when surrounded by teams, boards, investors, and customers. The conversation explores the myth of the “hero founder,” the uncomfortable role luck plays in business success, and why great teams can still fail when timing, regulation, or product-market fit work against them. Mike also shares lessons on moving fast without creating chaos…
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