In this very special, in-person episode, hosts Will and The Unrepped Founder discuss entrepreneurship, technology, and social impact. Jerry shares insights from his recent visit to Waterloo’s Socratica Symposium while Will recounts his experience at an entrepreneurial “F-Up Nights” event. The boys then talk about the cultural differences between Silicon Valley and Canadian business environments, the power of AI tools for entrepreneurs, employee ownership models, and ways to build authentic communities around projects. The boys end the show with a conversation about how to make the pod a platform to help others make meaningful impact. We hope you enjoy![00:00:00 – 00:04:05] Episode introduction. Jerry, The Unrepped Founder discusses his recent experience at the Socratica Symposium in Waterloo, a student-run event showcasing independent projects. He expresses optimism after seeing the talent and creativity of student presenters.

[00:04:05 – 00:07:06] Will shares his experience at “F-Up Nights,” where entrepreneurs discuss their failures. He highlights three companies including Othership, a Canadian wellness company expanding to New York that began as a backyard sauna and cold plunge project.

[00:07:06 – 00:09:10] Discussion about the current US-Canada tariff situation. Jerry suggests viewing it as an opportunity, noting increased interest in the Canadian Armed Forces Reserves and encouraging entrepreneurship as a patriotic duty.

[00:09:10 – 00:13:50] The hosts compare cultural differences between Canadian business environments and Silicon Valley. Jerry describes the more hierarchical nature of Canadian business settings versus the more open, idea-focused atmosphere in San Francisco.

[00:13:50 – 00:20:30] Deep dive into technology and AI. Jerry explains why he’s learning to code despite AI advancements, suggesting now is the best time to learn as AI tools can augment human abilities. He shares personal experiences using premium AI tools for research.

[00:20:30 – 00:25:00] Will discusses his vision for the podcast as a platform to help people make progress in areas like affordable housing, healthcare, and education. He emphasizes the value of sharing knowledge so others don’t need to spend years learning systems.

[00:25:00 – 00:30:38] Conversation about distribution, design, and marketing. Will references Naval Ravikant’s concept of leverage through code and media, noting that while Jerry focuses on code, he focuses on media. They discuss how feelings drive decision-making.

[00:30:38 – 00:37:00] The hosts explore the Maya Angelou quote: “People will forget what you said, people will forget what you did, but people will never forget how you made them feel.” They analyze Apple’s success through this lens and discuss how emotional connection remains critical in an AI-driven world.

[00:37:00 – 00:43:18] Discussion about employee ownership models. Will shares ideas about extending ownership to healthcare workers like PSWs, while Jerry notes how Silicon Valley’s success partially stems from distributing ownership to employees who help build companies.

[00:43:18 – 00:47:00] The hosts brainstorm ways to give their audience ownership in the podcast, considering how to create virtuous cycles that strengthen the show while genuinely helping viewers and guests.

[00:47:00 – 00:50:20] Closing thoughts and future goals. Jerry expresses his desire to help people start side projects that could become businesses. Will shares his goal of cross-pollinating ideas between entrepreneurs and artists.

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