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98 - The Sales Trick That Nearly Ended a Founder's Career
Episode 98 • 24th September 2026 • The Breakout CEO • Jeff Holman, Fractional General Counsel for CEOs and Founders
00:00:00 00:50:51

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Most CEOs never admit what they are bad at, and it costs them the exact hires and decisions that could help their business scale. Larry Gould built one of the world's largest language companies, The Big Word, and years earlier built and sold a recruitment business, but neither started with a plan. Both trace back to moments most founders would rather bury: a childhood spent selling comics door to door for ice cream money, a misdiagnosed medical condition that pushed him out of school at fifteen, and a sales job crisis where a suspiciously low expense report nearly got him fired for dishonesty. Instead of losing his job, Larry was reassigned into international sales, where a lack of budget for support staff forced a decision, insisting on translated materials and direct communication with clients in their own language, that eventually became the foundation of his translation business.

In this episode, Larry walks through the operating philosophy he still uses today: knowing exactly what he is not good at, whether that is finance or technology, and building his team and his leadership decisions around people who are clever where he isn't, then letting them go once they stop being the sharpest option as the business grows. He also unpacks the framework behind his obsession with the word irresistible, a discipline he pushes on every client, employee, and investor conversation, and why most CEOs cannot answer a simple question about what makes their own company worth choosing over the competition.

Larry Gould is a serial entrepreneur, founder of The Big Word, and a mentor to founders at Cornell Tech. (Guest website not confirmed in transcript — recommend confirming with Larry's team before publishing.)

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