For many founders, hitting $5 million in revenue feels like running into an invisible wall. Growth stalls, energy drains, and the path forward becomes murky. Alexis Sikorsky, who successfully navigated a nine-figure private equity exit, identifies three critical bottlenecks that trap companies at this stage.
The Founder Trap
The first obstacle? Founder exhaustion that goes beyond simple overwork. At this revenue level, many CEOs remain entangled in every business thread, unable to distinguish between urgent and truly important tasks. The solution requires brutal honesty about what only the founder can do.
Sikorsky recommends a simple exercise: list every task you handle, then ruthlessly identify which ones genuinely require your unique expertise. High-stakes client relationships, strategic hiring, and major sales deals might make the cut. Sitting in engineering meetings? Probably not. Everything that doesn’t pass this test should move off your plate immediately.
Financial Visibility Matters
The second trap involves financial data—or more specifically, how founders consume it. Some review financials quarterly, which Sikorsky compares to flying a plane without instruments. Others drown in 200-page reports that obscure rather than illuminate.
The sweet spot? A curated dashboard of 10-20 metrics updated monthly. These should directly tie to business objectives: cash flow, gross margin, customer acquisition costs, and lifetime value. Complexity kills decision-making. Clarity drives it.
Leadership That Scales
Perhaps the toughest challenge involves upgrading leadership without breaking the bank. Is that cousin handling accounting? The marketing manager who grew with the company? They might be wonderful people who simply lack the expertise for what comes next.
Hiring a full-time CFO can consume half your EBITDA, yet the role often proves essential. Sikorsky suggests considering fractional executives—but with a twist. Rather than assembling disconnected contractors, engage a cohesive fractional team that already collaborates effectively. This approach delivers senior expertise without the coordination headaches.
Cultural Evolution
As companies scale, the original family atmosphere inevitably shifts toward process and structure. Fighting this change wastes energy. Instead, guide it intentionally while preserving core founder values that create a competitive advantage.
Sikorsky emphasizes that strong founder-led cultures—think Tesla or OpenAI—can differentiate companies in crowded markets. Replacing the CEO prematurely often destabilizes organizations during this critical growth phase.
Preparing for the Exit
For founders eyeing private equity, preparation cannot start early enough. PE firms analyze more than current cash flow—they evaluate three-year potential, client quality, scalable processes, and acquisition opportunities.
Sikorsky advises founders to “dress the bride” by cleaning up EBITDA, removing one-time expenses, and demonstrating clear growth trajectories. Learning PE language and expectations accelerates the process. Know your number—the exit value that achieves your personal goals—before entering conversations.
The journey from $5 million to $20 million and beyond demands different skills than those that built the company initially. Success requires letting go of what got you here, embracing new leadership models, and maintaining crystal-clear visibility into what drives your business forward.
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John is the Amazon bestselling author of Winning the Battle for Sales: Lessons on Closing Every Deal from the World’s Greatest Military Victories and Social Upheaval: How to Win at Social Selling. A globally acknowledged Sales & Marketing thought leader, speaker, and strategist, he has conducted over 1500 video interviews of thought leaders for Sales POP! online sales magazine & YouTube Channel and for audio podcast channels where Sales POP! is rated in the top 2% of most popular shows out of 3,320,580 podcasts globally, ranked by Listen Score. He is CSMO at Pipeliner CRM. In his spare time, John is an avid Martial Artist.
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