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Grief & Pizza

Navigating the Product Journey with Andrew Askins

Mar 5, 2025
01:08:45

In this episode, we're talking to founder Andrew Askins about his experience growing an agency, getting acqui-hired, and then getting fired. We talk about company culture, the unique challenges of being a founder, and what it's like to bootstrap a software business.
 
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Takeaways

  • Selling a business creates unexpected emotional challenges, particularly around maintaining team culture and transparency during transition
  • The shift from founder to employee requires significant identity adjustment and emotional processing
  • Mindfulness practices and somatic therapy provide practical tools for managing entrepreneurial stress and anxiety
  • Successful entrepreneurship requires balancing optimistic vision with realistic anxiety management
  • Strong partnerships can provide essential emotional and strategic balance in business leadership
  • Teaching and public speaking effectiveness comes from authentic storytelling rather than technical perfection
  • Fear of judgment often blocks creative potential more than actual skill limitations
  • Building genuine community and psychological safety unlocks both team and individual growth

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