The Checkout

Overstaffed, Underprofitable: How Founders Should Think About Hiring


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Growing fast should feel like winning.
So why do so many founders end up more stressed, less profitable, and questioning their own decisions as revenue climbs?
In this episode, we break down one of the most uncomfortable but critical questions founders face as they scale:
Are you actually building a better business — or just hiring your way into chaos?
The conversation starts with a real founder scenario:
• Revenue is up 200% year over year
• The company used to be profitable
• Now it’s losing money
• The team’s solution? Hire more people
From there, we unpack what’s really happening beneath the surface.
This episode covers:
• The hidden danger of overhiring during growth
• Why “we need more people” is often a symptom, not a solution
• How to tell if a role is actually contributing to revenue or profit
• The difference between scaling output vs scaling overhead
• When losing money can make sense — and when it absolutely doesn’t
• Why chasing top-line growth can quietly destroy founder clarity and decision-making
• The mental and financial cost of “speedrunning” to $100M
• How experienced operators think about stress, risk, and sustainability
• Practical frameworks for hiring lean without stalling growth
You’ll also hear candid takes on:
• The myth that bigger teams automatically mean better execution
• Why many brands hit a wall around certain revenue milestones
• How to think about hiring when you’re not a multi-time operator
• The difference between scaling with confidence vs scaling in survival mode
This is not a hype episode.
It’s a reality check for founders who are growing fast and wondering if the pressure they feel is normal—or a warning sign.
If you’re a founder, operator, or growth lead asking yourself:
• “Should I slow down?”
• “Did I overhire?”
• “Am I building something sustainable—or just expensive?”
This episode will help you think more clearly about what comes next.

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The CheckoutBy Modern Commerce Media