Why $20M Doesn’t Mean You’ve Made It #218

📅 July 2, 2025 ⏱️ 27:06 🎤 John, Jack

Chapters

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0:31

$20M is Small Business

The hosts discuss why a $20 million business is still considered a small business, often personality-driven and lacking full departmental sophistication.
4:45

When to Hire C-Suite

They debate the appropriate revenue size for hiring C-suite executives like a CFO or CMO, concluding that 20 million is often too small for truly effective C-suite roles.
10:47

Problems Remain Constant

The discussion highlights that business problems like headcount and cash flow issues don't disappear at higher revenue levels; they often become more complex.
17:04

Building Real Leadership Teams

The hosts share insights on building effective, 'real' leadership teams that can handle strategic tasks with minimal owner supervision, emphasizing internal promotions.
28:29

Leadership for Velocity

They explore how investing in leadership development, especially by promoting from within, can increase business velocity and success rate compared to hiring externally.
40:16

Headcount Defines 'Real' Business

The episode concludes by arguing that a business needs at least 100 employees to be considered 'real' and have fully developed departments, beyond just revenue.

Speakers

John

Host

Jack

Host

Key Takeaways

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Reaching $20 million in revenue doesn't mean your business is 'made it'; it's still a small business requiring significant owner involvement.

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Prioritize investing in a leadership development program to consistently elevate frontline team members to leadership roles, rather than relying solely on external hires.

✦

Understand the true roles of C-suite positions; at $20 million, you likely need a controller or senior accountant, not a full CFO, to manage finances effectively.

✦

Recognize that cash flow and headcount challenges don't disappear as your business grows; they evolve and require more sophisticated management.

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Cultivate an environment of upward mobility for high-achieving employees to retain talent and leverage their understanding of your business and culture.

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Aim to hire internally for management positions whenever possible, as the success rate for internal promotions is significantly higher than for external hires due to cultural alignment and existing knowledge.

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← Buy vs. Build: Start or Acquire Your First Business? #220

We Hit $1M Profit — Here’s Exactly How We Did It #217 →