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
Matt's Books on Amazon
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