Navigating the Product Journey with Andrew Askins
From Grief & Pizza by Oki Doki Digital Inc.
March 5, 2025 · 1h 9m · Episode 13
About this episode
Andrew Askins shares his journey of growing an agency, the emotional challenges of being a founder, and insights on managing entrepreneurial stress.
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. Links AndrewAskins.com MetaMonster.ai 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 & Guests Marie Poulin - Host…
People in this episode
Hosts: Marie Poulin, Benjamin Borowski
Guest: Andrew Askins
Topics covered
- entrepreneurship
- company culture
- emotional challenges
- founder experience
- mindfulness
- software business
Keywords
- acqui-hired
- bootstrapping
- identity adjustment
- emotional processing
- entrepreneurial stress
- team culture
- storytelling
- community growth
Mentioned in this episode
Organizations: AndrewAskins.com, MetaMonster.ai
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