What actually breaks when a company scales—and why does it so often happen between 30 and 100 employees?

This conversation with Matt Blumberg goes straight to the uncomfortable truth: most companies don’t stall because of product or market fit. They stall because the CEO hasn’t scaled yet.

Matt has built companies from zero to $100M+, served as CEO and executive chair, advised hundreds of founders, and written the go-to books on being a startup CEO, CXO, and board member. In this episode, he shares the moments where he nearly broke himself—and the frameworks he developed to avoid breaking again.

This is a practical, honest discussion about feedback, coaching, leadership teams, boards, and why scaling yourself is the hardest (and most important) work a founder can do.

Key Discussion Points

00:00 – Why companies really break as they scale

01:40 – What “breaking” looks like for a CEO

03:00 – Matt Blumberg’s near-breaking moment as a first-time CEO

04:20 – Why getting a coach changed everything

07:40 – The real meaning of “scaling yourself”

09:55 – Why the 30–100 employee stage is so dangerous

11:40 – The two teams every CEO must scale: leadership & board

14:05 – How to actually invest in leadership team growth

16:40 – Coach vs mentor vs peer group (and why all three matter)

18:00 – How to ask for, process, and act on feedback

21:00 – Why operating systems become the company’s lifeblood

23:40 – When leaders must stop telling and start asking

26:00 – Why boards need to scale too

28:00 – Why being a student of the craft never stops

About Matt Blumberg

• LinkedIn: https://www.linkedin.com/in/blumbergmatt/
• Email: matt@markup.ai
• Personal Blog: https://startupceo.com (22 years of CEO insights)
• Company: https://markup.ai

Matt's Books on Amazon

• Startup CEO: https://www.amazon.com/s?k=startup+ceo+matt+blumberg
• Startup Boards: https://www.amazon.com/s?k=startup+boards+matt+blumberg
• Startup CXO: https://www.amazon.com/s?k=startup+cxo+matt+blumberg

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