Measuring originality

That gap led Jonathan to launch Hupside, built to quantify something most people considered too subjective to measure: originality.

His view is that the AI era won't be won by whoever adopts technology most efficiently. It will go to people and organizations that best combine human originality with AI capability. One way to start is Hupside's OIQ Challenge, which identifies your originality archetype and how you approach novel problem-solving in ways AI can't replicate.

Assistant, not dictator

Jonathan's bet on who comes out ahead is clear.

"In the long run, people who are servant leaders and people who use AI where AI is an assistant not a dictator, are going to be more productive and are going to win."

Back in the arena

After years of advising entrepreneurs, Jonathan is running a startup again. He describes it as both humbling and clarifying: late-night design sessions, product decisions, and the real question of whether the market will embrace what you built.

He compares it to inviting everyone to a party at seven o'clock and wondering if anyone will show up. That vulnerability, he says, is the source of the passion behind successful ventures.

It also connects to a tension he noticed decades ago, between wanting to be good and wanting to be rich. He's spent his career pursuing ventures that serve both. For Jonathan, entrepreneurship answers two basic questions: why am I here, and what do I do?