Winners Welcome Podcast, Episode 6 with Deon Nicholas, CEO and Founder of Espa AI.

Deon Nicholas has been early to AI for as long as he can remember. In 2009, while still in high school in Edmonton, he interned at one of Canada’s first AI labs, working on computer vision for cancer detection and teaching a simulated robot how to walk. Almost two decades later, he’s built one of the most quietly influential careers in the space, founding Forethought and raising over $115M before the current AI boom made every investor an AI investor.

Now he’s doing it again with Espa, an AI executive assistant designed to live across your email, calendar, and daily workflows. The thesis is simple but ambitious. Executive-level support has historically been reserved for CEOs and the top 1%. Espa is built to make that kind of leverage accessible to founders, operators, realtors, small business owners, and anyone else trying to achieve more.

In this episode, Deon walks us through his journey from competitive programmer at the University of Waterloo to AI founder in Silicon Valley, what he’s seeing in the agentic AI shift that most people are still missing, how he thinks about building and recruiting world-class talent, and why storytelling became one of the most important skills he developed as a founder. He also opens up about the humility-confidence balance behind his approach to building, and how that mindset shapes everything from product decisions to who he hires.

This episode is brought to you by Gunderson Dettmer, the number one law firm in venture capital globally, built exclusively for the innovation economy and trusted by the founders and investors defining what comes next.

Whether you’re building, investing, or simply trying to get more out of every day, this conversation is worth your time.

About The Winners Welcome Podcast

The Winners Welcome Podcast brings elite founders and top investors into thoughtful conversations on pushing past possible, sharing the conviction, standards, and lessons behind building generational companies.

About Harlem Capital

Harlem Capital is a venture capital firm that backs the next generation of winners. The firm partners with exceptional founders with the irrational motivation to build generational companies. All Winners Welcome.

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