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The Real Cost of Entrepreneurship | Episode 8 - Bill Poston & Prof. Joe O'Mahoney

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Bill Poston's remarkable journey from truck stop motel clerk to successful consulting entrepreneur offers a masterclass in professional services growth. With disarming candor, he shares how his farm upbringing and hospitality background instilled the relentless work ethic that became his competitive edge at Deloitte and beyond.

After a decade at Deloitte that served as his "apprenticeship" in consulting fundamentals, Poston took the entrepreneurial leap to found Calypso, a firm focused exclusively on helping clients deliver on the promise of innovation. What began as a "bet on ourselves" quickly grew beyond expectations, with first-year revenues approaching $4 million. Yet success brought unexpected challenges – from the administrative burdens of running a business to the delicate balance of maintaining focus while pursuing growth opportunities.

Perhaps most fascinating is Poston's candid assessment of their missteps: expanding internationally too quickly, venturing into training that became "a huge distraction and commercial failure," and attempting government work that "proved futile." These hard-won lessons underscore a crucial truth about entrepreneurship – recognizing mistakes early and pivoting before they become fatal is as important as getting things right initially.

Today, Poston channels these experiences into LaunchBox, helping new founders launch professional services firms by providing both business infrastructure and capital. His screening process focuses on two critical questions: Do you want to build a business to scale rather than a lifestyle practice? And are you commercially viable – able to sell work, not just deliver it? This practical wisdom exemplifies why Poston has succeeded where many professional services entrepreneurs falter.

Whether you're considering entrepreneurship, growing a consulting practice, or simply fascinated by the inner workings of professional services, this conversation delivers invaluable insights from someone who's navigated the journey from startup to successful exit. Ready to transform your consulting firm's equity value? Visit equitysherpa.com to discover how we help consultancies quadruple their worth over a two to four year period.

Prof. Joe O'Mahoney helps boutique consultancies scale and exit. Joe's research, writing, speaking and insights can be found at www.joeomahoney.com



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