What It Takes to Scale a Business | Executive Sessions Podcast
Tue Jan 27 2026
On MiddleGround’s twenty-seventh episode of Executive Sessions, Jane Sidebottom and Phil Arra share practical perspectives on scaling businesses.
This episode covers:
1. Why scaling starts with a clear vision, not just growth targets
2. How growth exposes operational gaps and system limitations
3. The role of focus and discipline as complexity increases
4. What successful companies do differently to scale with intention
Check out our company blog recapping the episode: https://bit.ly/4t3Qyxa
Learn more about MiddleGround Capital: https://middleground.com/
Follow MiddleGround Capital on LinkedIn: https://www.linkedin.com/company/middlegroundcapital/
Follow John Stewart on LinkedIn: https://www.linkedin.com/in/johnstewartky/
Find Jane Sidebottom on LinkedIn: https://www.linkedin.com/in/jane-sidebottom/
Find Phil Arra on LinkedIn: https://www.linkedin.com/in/phil-arra/
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On MiddleGround’s twenty-seventh episode of Executive Sessions, Jane Sidebottom and Phil Arra share practical perspectives on scaling businesses. This episode covers: 1. Why scaling starts with a clear vision, not just growth targets 2. How growth exposes operational gaps and system limitations 3. The role of focus and discipline as complexity increases 4. What successful companies do differently to scale with intention Check out our company blog recapping the episode: https://bit.ly/4t3Qyxa Learn more about MiddleGround Capital: https://middleground.com/ Follow MiddleGround Capital on LinkedIn: https://www.linkedin.com/company/middlegroundcapital/ Follow John Stewart on LinkedIn: https://www.linkedin.com/in/johnstewartky/ Find Jane Sidebottom on LinkedIn: https://www.linkedin.com/in/jane-sidebottom/ Find Phil Arra on LinkedIn: https://www.linkedin.com/in/phil-arra/