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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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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
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
- Benjamin Borowski - Host
- Andrew Askins - Guest
15 episodes
