In the latest episode of the Everlasting Fulfilment Podcast, host Nico van de Venne welcomes Leanne Linsky, a fascinating entrepreneur who has navigated the challenging path from stand-up comedy to tech founder. Their conversation illuminates the emotional rollercoaster that defines the entrepreneurial experience, particularly focusing on what Nico terms “founder syndrome” and “CEO disease.”

I want to learn and hear what everybody has to say, and if you ask someone for their opinion, they have one. But I also have to recognize does that feedback really pertain to the direction I’m going? Is that person an expert in this particular industry or is it coming from a place of founder experience or investor experience? So I’m not so overwhelmed anymore or trying to spend all of my time creating a pitch deck that everybody likes versus just getting the work done.

Linsky describes this phenomenon as a paradoxical experience: on one hand, there’s the powerful, innate drive to solve a problem you’re deeply passionate about. On the flip side lurks isolation, fatigue, and constant questioning of purpose. This cycle of enthusiasm followed by doubt represents the entrepreneurial journey that many founders experience, but few discuss openly. “Side effects also include getting fatigued and feeling isolated,” Linsky explains, highlighting the less glamorous aspects of the founder lifestyle.

What makes Linsky’s story particularly compelling is her unique background. Before founding her tech company, she spent years immersed in comedy, training at the prestigious Second City and performing across multiple cities. This unconventional path provided her with invaluable skills in communication and audience engagement that would later prove essential for her entrepreneurial venture. Her journey took an unexpected turn when, after being laid off from a Fortune 500 role she had held for nearly 13 years, she embraced risk – packing two suitcases and moving to New York to pursue comedy full-time.

The genesis of her company, Plauzzable, came from a practical problem she encountered as a comedian in Los Angeles. Finding herself spending more time in traffic than on stage, she began exploring online alternatives that would allow performers to connect with audiences without geographic limitations. What started as a personal solution evolved into a comprehensive platform designed specifically for live comedy performances – describing it as “the Netflix of comedy, except it’s all live.”

Perhaps the most valuable insights from the conversation centre around how Linsky transformed her relationship with isolation. Rather than viewing it exclusively as a negative aspect of entrepreneurship, she’s learned to appreciate quiet reflection time. “I’ve really become better at filtering what information is coming at me,” she explains, noting how early in her journey she was taking advice from everyone without discrimination. Now, she carefully considers the source and relevance of feedback, asking critical questions like “Is that person an expert in this particular industry?” or “Is it coming from a place of founder experience or investor experience?”

This evolved perspective allows her to focus on execution rather than endless refinement based on conflicting advice. Instead of “trying to spend all of my time creating a pitch deck that everybody likes,” she prioritizes “just getting the work done.” Linsky now views isolation as an opportunity for clarity rather than a burden – a sentiment that resonates with many successful entrepreneurs who have learned to trust their own vision while selectively incorporating outside perspectives.

For founders struggling with isolation, Linsky’s journey offers a powerful reframing: the quiet moments of reflection can become your competitive advantage. By deliberately creating space to process information and connect with your actual users rather than other industry voices, you develop a clearer path forward. As she wisely notes, “Entrepreneurship is an evolving piece of art. It’s never done; it’s not a destination, it’s a journey.”

The conversation concludes with Linsky’s powerful metaphor for the entrepreneurial experience: “Sometimes I’m pushing the boulder up a mountain by myself, and sometimes the boulder’s running me over.” Yet despite these challenges, what keeps her motivated is seeing people using her platform – connecting, collaborating, and creating. It’s this tangible impact that continues to fuel her journey through both the highs and lows of building a business from scratch.

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