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.

Will and the Unrepped Founder are back and this episode gets heated! The boys debate the current state of Canadian-American relations amid escalating trade tensions, the exodus of Canadian tech talent to Silicon Valley, and how entertainment shapes modern political discourse. The conversation touches on the Alberta health scandal, Ontario's recent provincial election, and the fundamental question of how Canada can maintain economic sovereignty while living next to a global superpower.

The Toughest Issues, The Realest Conversations—No Edits, Just Solutions.

[00:00:00 - 00:04:00] Episode introduction and technical setup. Jerry discusses his recent trip to the West Coast and observations about Canadian tech talent in the Bay Area.

[00:04:00 - 00:07:09] Breaking news about the RCMP launching an investigation into the Alberta health scandal; discussion of the recent Ontario provincial election where the Progressive Conservatives won an even stronger mandate.

[00:07:09 - 00:13:16] Examination of U.S. tariffs on Canada, with hosts questioning Trump's true motivations and endgame. Discussion of how Doug Ford is considering electricity surcharges to New York, Minnesota, and Vermont in response.

[00:13:16 - 00:18:50] Conversation about politics becoming entertainment ("kayfabe") and how Trump understands that attention is gained through entertainment. Debate about how this affects public discourse and engagement.

[00:18:50 - 00:24:39] Discussion of Canadian economic sovereignty, the patriotic duty to start businesses, and how the trade war has exposed Canada's reliance on American technology and products.

[00:24:39 - 00:30:02] Exploration of Canadian cultural identity in comparison to American and Korean cultural exports. Jerry argues that America often adopts Canada's best talent while K-pop shows how cultural exports can create economic value.

[00:30:02 - 00:36:41] Discussion of Canadian identity, with observations that American cultural influence is so strong that Canadians often don't claim their own cultural accomplishments. Debate about whether Americans would discard their Canadian connections when convenient.

[00:36:41 - 00:43:01] Debate about whether Trump would seriously consider annexing Canada, with Jerry suggesting that expanding U.S. territory might appeal to Trump's desire for a historical legacy.

[00:43:01 - 00:48:57] Conversation about the shift in political discourse, the challenges faced by the political left, and how right-wing commentators have better adapted to the social media environment.

[00:48:57 - 00:56:58] Debate about the financialization of the economy, with Will criticizing Silicon Valley's business models like Uber as extractive rather than genuinely innovative. Jerry defends the tech industry as creating actual value.

[00:56:58 - 01:10:12] Heated debate about whether technology and Silicon Valley have genuinely improved lives or simply created new forms of exploitation. Discussion using sports leagues (NBA vs. NFL) as an analogy for economic efficiency versus what's best for society.

[01:10:12 - 01:27:00] Jerry advocates for entrepreneurship as a solution to Canadian brain drain, while Will argues that not everyone should be forced into entrepreneurship. Discussion about the importance of building Canadian tech sovereignty.

[01:27:00 - 01:31:25] Wrap-up and closing thoughts. The hosts agree on the importance of healthy debate and different perspectives in finding the best solutions for Canada's challenges.

“I hope I didn’t make my mom cry.”

In 2024, a monumental shift occurred in the fear complex of Americans. For the first time in over a decade, the fear of public speaking (glossophobia) was surpassed as one of America’s greatest fears by… a fear of sharks?

Reading this sparked two immediate reactions. The first was an urge to congratulate sharks on their huge 2024 (great work, guys! 🥳). The second was a wave of relief, hoping I’d never again have to hear what I consider one of the great made-up stats of our time at another conference, wedding, or corporate event. Because let’s be honest—there’s simply no way public speaking is actually anyone’s #1 fear. And if it is, kindly send them my way.

In high school, I was a fairly proficient public speaker and debater (yes, I know the joke you’re laughing at right now—get your mind out of the gutter 😂). It’s probably the most important skill I developed during those years. Aside from the odd occasion, I haven’t regularly found myself in front of large crowds since, but I’ve been fortunate enough to coach friends and family for their own speeches and presentations—including some impressively important ones.

There’s a saying that goes, “Those who can’t do, teach,” which, besides being wildly insulting to all teachers, would be more accurately rephrased as, “Those who can’t play, coach.” Because everyone’s playing days come to an end eventually.

Yesterday, my mother, Christiana Egi, was invited to speak at the Customer Experience for the Public Sector (CXPS) Summit 2025 in Toronto. She was understandably excited about the opportunity—especially given the speaker lineup, which was almost entirely made up of high-level officials from federal, provincial, and municipal governments and agencies. The excitement, however, was accompanied by nerves. She was eager to do well and deliver the impactful message she had prepared about patient-centred care.

So, what did she do? She asked her eldest (not favourite!) son to help with her speech—the result of which you can see in the video above. In the interest of full transparency, she did ask me for help over a month ago, but hey, time gets away from us all.

Now, if we’re going to talk about fear, I have to admit: I was a little nervous to make this post. I think the general perception of me is much kinder and gentler than the one held by my family and close friends. Just yesterday, I was messaging a near and dear friend, moaning about how I wish I could clone myself to better handle my workload. Their swift response? “no1 needs that.” (Maybe a tad too swift there!)

Before posting, I shared the video with my mom to make sure she was comfortable with how she—and our dynamic—came across, especially given the tense exchanges at the start of our practice. Given the time constraints, my coaching style probably created the tension. I’m pretty much the middle school basketball coach who walks into practice and immediately yells out, “Alright, basketballs away! To the baseline, everybody!”

Combining her (justified) anxiety about last-minute changes with my…approach(?) was dicey at first—I actually thought I was going to make her cry. But eventually, we got to where I knew we would. I have immense faith in my mother, because as someone who eats, sleeps, and breathes care, how could she not be great? All she had to do was be herself. My only job was to be Fifth Business and help her get there.

And she most certainly did. Congratulations, Mom.

Always,

Will

“Hold up, let her cook.”

That’s what I was thinking as I listened to Lydia Greene during the first (!) episode of our (co-host: The Unrepped Founder)live-streamed podcast, We’ll Do It Live.

The goal of the podcast is to have live, unfiltered conversations about today’s most complex issues—bringing in different voices in the hopes of finding real solutions. The lack of progress in housing, healthcare, education, and more baffles me. We (and I’m using ‘we’ almost facetiously) have never been richer, yet things seem to be getting worse despite all that money.

I’m not an ideologue, but I am an idea-lover. The best idea should win, and I truly don’t care where it comes from.

Check out the show—we hope you’ll subscribe to the pod!