Episode 38: From 10 to 50 People: Why Startup Habits Begin Failing

Episode 1 in the series: Scaling Growth

When your company is small, hustle works.

Everyone wears every hat. The founder can still check every job, meet every client, and fix every problem.

But by the time you hit 50? The very habits that fueled your growth are the ones pulling you under.

In this first episode of the Scaling Growth series, James Mayhew explains why the startup habits that worked at 10 or 20 people begin to fail at 50 — and why those same patterns will stall you again before you hit 100. Using examples from manufacturing, contracting, insurance, and specialty clinics, James shows why scaling requires new systems, leaders, and disciplines — not just more effort.

This episode is for founders and CEOs who are feeling the weight of growth and wondering why things suddenly feel harder instead of easier as their business expands.

What you’ll take away:

• The difference between growth and scaling — and why most founders confuse them.
• Why habits like hustle, “everyone wears every hat,” and fixing things yourself break down at 50.
• The warning signs: bottlenecked decisions, blurred roles, and accountability slipping.
• Real examples of scaling pitfalls across manufacturing, construction, insurance, and specialty healthcare practices.
• Why your habits — not your people — are capping your growth.

Reflection questions:

• Where are you still running your company on small-team habits that don’t scale?
• What’s one system you know you’ve outgrown but haven’t replaced yet?
• If you kept running your company at 50 the same way you did at 10, what’s the real cost — to you, to your team, and to your customers?

Links & Resources:

• The Next Question Guide → NextQuestionGuide.com
• Connect with James on LinkedIn → linkedin.com/in/jamesmayhew
• Learn more at → JamesMayhew.com