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Leanne Linsky's journey from stand-up comedian to tech founder offers a masterclass in resilience and adaptability. What began as a practical solution to spending "more time on the highway than on any stage" evolved into Plauzzable - a groundbreaking platform where comedians perform live online for global audiences, free from of geography or gatekeepers.

This conversation explores the emotional roller coaster of founder syndrome, where passionate problem-solving exists alongside isolation and self-doubt. "Side effects include getting fatigued, feeling isolated, and questioning what am I doing?" she shares candidly. Yet her perspective on entrepreneurial solitude evolved dramatically over time, transforming from a perceived weakness into a strategic strength.

After years in comedy, including training at the prestigious Second City and producing shows in New York, she faced a pivotal moment when she was laid off from her Fortune 500 job. Rather than playing it safe, she packed two suitcases and moved to New York, immersing herself in comedy before eventually creating a tech solution for performers. Her story includes returning to school at age 50 for a master's degree in innovation and entrepreneurship - a commitment to continuous learning that helped bring her vision to life.

What makes her approach remarkable is how she learned to filter advice and feedback. Early on, she absorbed everyone’s input, but learned to ask: “Is that feedback really pertinent to the direction I'm going? Is that person an expert in this particular industry?” That discernment let her focus on execution, not endless revision. Most importantly, she reframed isolation as reflection time - a space to clarify vision and build resolve.

Listen to this episode for practical wisdom on building both a business and the inner resources needed to sustain the entrepreneurial journey over the long term. You'll find inspiration in Leanne's approach to "pushing the boulder up a mountain" with purpose and perspective.

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