Insights: Meet Jeremiah Onaolapo

Cybersecurity Expert, Entrepreneur, and Community Builder at Hula

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If you’ve ever crossed paths with Jeremiah Onaolapo at Hula, you probably walked away with a smile, a great conversation, or even a fresh perspective on tech. A former University of Vermont professor of cybersecurity, Jeremiah traded in academia to dive headfirst into entrepreneurship, founding Allegory Cyber, a company focused on cybersecurity training and education.

 

While Jeremiah’s professional expertise spans cybersecurity, AI, and the deeper layers of business tech, it’s his approachable, ever-curious spirit that really sets him apart. Whether he’s discussing the "Five Whys" method for getting to the root of a problem or quoting the Rolling Stones to explain business resilience, Jeremiah brings a thoughtful, grounded lens to the world of startups and tech.

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He’s also the founder of The Smart Biz Meetup, a monthly lunch gathering hosted right here at the Preppi Eatery at Hula, every last Thursday of the month. It’s a space for tech-minded entrepreneurs to connect, share ideas, and learn from one another—a natural extension of Jeremiah’s belief in the power of community.

 

“I learn a lot from fellow Hula entrepreneurs—and I hope they learn some things from me too,” he says. “Life is a succession of lessons in figuring out ‘the right track.’ I’m still figuring it out, but when your skills and interests align with the challenge in front of you, you’re probably close.”

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The Smart Biz Tech lunch in action, with Jeremiah at the center.

True to form, Jeremiah is always up for a chat, a laugh, or a beverage with both old friends and new faces. His grounded outlook on success and failure reminds us that setbacks are often better teachers than wins, and that “figuring it out” is part of the process. As he puts it, “Failure forces one to re-evaluate options and pivot if necessary. Success, if not well handled, can go to one's head.”

 

If you’re new to Hula or just haven’t said hello yet, be sure to catch Jeremiah at the next Smart Biz Tech lunch—or better yet, swing by for a conversation anytime. With his wealth of knowledge and open-door attitude, he’s a great example of what makes the Hula community shine.