Homecoming Highlights: Darrell Etherington Returns to Windsor with Insights on Tech, Talent, and Community

In the fast-paced world of startups, connections are everything. At WETechAlliance, we know that the magic of innovation and growth happens when people collide. The second event in our Tech Connect Summer Socials: Downtown Edition series, “Tech Talk and Taps”, was a prime example, featuring the homecoming of our very own superstar alumnus, Darrell Etherington.

While attending the Ontario Centres of Innovations (OCI) DiscoveryX conference, I discovered that Darrell, a rockstar tech journalist and Head of Content at OMERS Ventures, also hailed from the University of Windsor. A quick message led to an instant and enthusiastic response, and before I knew it, Darrell was on board to meet at the OMERS Toronto office. Our chat, full of nostalgic tales from his days at Vincent Massey and the University of Windsor, sparked a determination in me to bring him back to inspire our community.

When planning our Tech Connect Summer Socials, we aimed for diverse content and experiences for both founders and the community. Inviting Darrell to Windsor was a no-brainer.

At WETechAlliance, we create opportunities for epic collisions—moments where ideas, people, and opportunities intersect in exciting ways. Our workshops, keynotes, fireside chats, and networking events are designed to educate and connect founders, talent, and community. These gatherings fuel community and economic growth. By bringing leaders like Darrell back to their roots, we offer our community the chance to benefit from his valuable insights. Darrell reconnects with his origins, while attendees have the opportunity to learn, connect, and build new relationships.

For those who missed it, meet Darrell Etherington! He’s a tech journalism superstar and the Head of Content at OMERS Ventures. With a decade of experience at TechCrunch, Darrell has covered everything from AI and robotics to space exploration and self-driving cars. Now, he scouts out the coolest tech startups and shapes investment strategies at OMERS Ventures. A proud University of Windsor alumnus, Darrell is known for his engaging and entertaining communication style, making him a favorite speaker at tech conferences.

Darrell’s talk provided a wealth of knowledge and insights. We know people love lists, so here are the top 11 things we learned from our chat:

1. Navigating Media and Investor Relations: Darrell highlighted that building strong relationships with media and investors requires clear communication, genuine passion, and an understanding of stakeholders’ interests. Entrepreneurs should convey a compelling and passionate message about their product while aligning it with the interests of their audience

“Building relationships with media and investors is about conveying passion and having a clear problem and solution statement.”

2. Interviews with Tech Executives: Darrell shared his experiences interviewing prominent tech figures like Mark Zuckerberg and Bill Gates. He noted how these high-profile individuals, despite their significant achievements, come across as normal people with their own struggles and quirks.

“People like Zuckerberg and Gates, they don’t in person seem all that different from friends I had in high school.”

3. Common Traits of Successful Founders: Darrell identified common traits among successful tech founders, such as a singular vision, resilience, and the ability to pivot and adapt their ideas. These traits are often more important than the initial idea itself.

“The idea that hits for them is not usually the idea they started with… the why usually remains relatively the same.”

4. Economic Cycles and Innovation: Darrell discussed how economic downturns often lead to the emergence of some of the best startups, as these challenging times foster innovation and resilience among entrepreneurs.

“Out of these big, sort of black swan type events like the crash, you get your best cohorts and your best vintages on startups.”

5. AI’s Current and Future Impact: Darrell elaborated on the current hype around AI, emphasizing that while AI has significant potential, it may be near the peak of its usefulness in certain areas. However, the exploration of domain-specific AI applications holds promise for future innovations.

“With AI, it really does feel different. It feels much more like the movement from general web into mobile.”

6. Midsize Cities as Tech Hubs: Darrell emphasized the potential of midsize cities like Windsor to become thriving tech hubs. He highlighted advantages such as lower costs, proximity to educational institutions, and the ability to hire internationally. These factors can create a conducive environment for tech startups and innovation, differentiating them from larger, more saturated tech markets.

“Smaller markets have unique advantages… we can hire internationally in a way that Silicon Valley can’t, and that’s a huge advantage.”

7. Future of Tech Talent: Darrell emphasized the importance of tech professionals becoming familiar with AI tools while recognizing the lasting importance of traditional coding and engineering skills. He encouraged professionals to embrace and utilize new technologies.

“Get comfortable with the tools, get in there, start using them… traditional coding and engineering skills are going to be really useful for a long time.”

8. Challenges for Startups:  Darrell highlighted the critical need for startup founders to have a clear and strong vision, along with the resilience to navigate challenges and pivots. He pointed out that the most successful founders are those who are deeply connected to the problems they are solving.

“The best founders are the ones closest to the problems they solve. It’s very, very hard at some point and for a long time probably, and that singularity of vision helps them stick it out.”

9. Early Tech Influences: Darrell’s early exposure to computers and video games, particularly Starcraft, sparked his passion for technology and problem-solving. He highlighted how Starcraft, with its campaign builder, functioned like programming and ignited his interest in tech.

“I remember one thing that was very formative was Starcraft… it was essentially like programming without having to know much about programming.”

10. Inclusivity and Community Building: Darrell emphasized the importance of diverse social events and outreach to underrepresented groups to create an inclusive tech community. By organizing a variety of events that cater to different interests and demographics, the tech industry can attract individuals from diverse backgrounds and make them aware that a career in technology is accessible to them.

“Having a variety of different types of social events is key… making people aware that tech is an industry they can go into.”

11. Effective Storytelling: Building a compelling narrative around your startup is essential for attracting investors, customers, and media attention. Darrell underscored the importance of clearly articulating the problem your startup solves and the value it provides.

“If you articulate the problem and I go, ‘Oh, that seems like a horrible problem,’ and then you articulate the solution and I go, ‘That’s such a clever solution,’ it almost doesn’t matter what the two things are, as long as you can clearly articulate it in a way that is graspable instantly.”

Thank you to everyone who attended and to Darrell for sharing his journey and wisdom. We look forward to many more events that inspire, connect, and drive our community forward. On that note, our final Tech Connect Summer Social: Downtown Windsor Edition is just days away. Join us in imagining downtown as a tech and innovation hub during Art Windsor-Essex’s AWE at Night on August 15th. More details here: Event Link.