Navigating the Product Journey with Andrew Askins

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

Creators and Guests

Benjamin Borowski
Host
Benjamin Borowski
Notion warlock at NotionMastery.com, Systems at WeAreOkiDoki.com, volunteer firefighter, hacker, DJ
Marie Poulin
Host
Marie Poulin
Taming work/life chaos with Notion • Leading NotionMastery.com • Online Courses • ADHD • Permaculture
Navigating the Product Journey with Andrew Askins
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