Jonathan Aberman is an entrepreneur, investor, and innovation strategist redefining how we measure human potential in an AI-driven world. As co-founder of Hupside, he is championing a new category—Original Intelligence—that identifies and quantifies originality as a business differentiator. He is also a partner at Ruxton Ventures, where he applies his expertise in venture investing and technology commercialization to support high-growth companies. Jonathan also brings a strong academic track record: he served as dean of the School of Business and Technology at Marymount University from 2019 to 2023 and currently serves as Visiting Entrepreneur and Strategic Advisor to the Frank J. Guardini School of Business at John Cabot University in Rome.

With a career spanning venture capital, academia, and tech commercialization, Jonathan is a trusted voice for leaders navigating AI transformation who want to center, not sideline, human intelligence. He has been named a “Tech Titan” by Washingtonian, included in the Washington Business Journal’s “Power 100,” and recognized by Virginia as one of its “50 Most Influential Entrepreneurs.” Jonathan’s leadership and insight have established him as a trusted guide at the intersection of innovation, entrepreneurship, and originality.

For readers who may be new to Hupside, can you share what the company does and what inspired you and your team to launch it?

We are in the midst of the most transformative technology era in history. As we have seen companies make major shifts to become more AI-driven, we identified a gap—the people who will work effectively with AI. Recent studies have shown that 95% of companies have not seen an ROI from AI adoption.

We built Hupside to provide a way to identify AI-ready talent through measuring Original Intelligence. Our Hupchecker platform quantifies originality through a new metric we call the Original Intelligence Quotient (OIQ). This gives organizations visibility into the AI-readiness of their people and how they generate novel ideas, both on their own and when working with AI. We were inspired to launch Hupside because while AI can make things faster and cheaper, it can’t create breakthroughs on its own. Original insight has always been the true driver of innovation, and in an AI-everywhere world, it’s also the only real differentiator.

How is the AI transformation similar to past major technological transformations, and how is it different for organizations?

Like other big technological shifts, AI is being adopted quickly because it offers clear efficiency gains. In that sense, it feels a lot like the early internet or cloud computing waves. Leaders see cost savings, faster processes, and productivity improvements. But here’s the difference: AI doesn’t generate the unexpected, it generates what’s likely. That creates homogenization at scale, and as a result, content, products, and even strategies start to look the same.

In past transformations, efficiency alone could sustain competitive advantage for a while. With AI, efficiency quickly becomes table stakes. To really benefit, organizations have to treat this not as a top-down tech rollout but as a bottom-up cultural shift that elevates originality alongside AI.

Why are the stakes for successful transformation so high this time?

The stakes are higher because AI doesn’t just change workflows, it changes the very nature of human contribution. If organizations only focus on efficiency, they’ll find themselves in a race to the bottom where everyone has the same tools, producing the same ideas, at the same speed. That erodes differentiation and long-term profitability.

On the flip side, organizations that intentionally combine AI with human originality will build lasting advantage. Original thinkers who know how to work with AI aren’t just useful, they’re essential to avoiding sameness, solving problems in new ways, and keeping innovation alive. That’s why getting it right is so crucial.

Many organizations are rushing to adopt AI, but you argue that AI readiness is less about the technology and more about people. What do you mean by that?

Too many leaders look at AI transformation as a technology project: plug in a new tool, cut some costs, and you’re done. But AI only delivers real value when people know how to use it well. How do we know they use it well? Through measuring Original Intelligence, which is predictive of the ability to adopt and optimize new tools. If your people rely on AI outputs without challenging them, you’ll just reinforce groupthink. But when people bring their own Original Intelligence to the table, AI becomes a multiplier rather than a crutch. AI readiness is fundamentally about people, and about whether they have the mindset and capacity to go beyond the obvious, think critically, and generate something truly new.

How does Hupside’s approach differ from traditional assessments that focus on personality, skills, or fixed rubrics?

Traditional assessments were built for a pre-AI world. They measure personality traits, productivity, or even creativity through subjective judgments. But those frameworks can’t tell you whether someone is truly original when they’re working with AI. Hupside is different. We measure outcomes, not traits.

Our Hupchecker tool evaluates how a person’s ideas compare against both human responses and AI baselines, mapping them into an “idea space.” This lets us see whether someone is expanding beyond sameness, and it gives organizations an objective measure of originality in action. It’s not about labeling people, it’s about surfacing the kind of thinking that creates strategic differentiation.

What are some of the most powerful ways your platform helps organizations build AI-ready teams and guide training or development?

The power of our platform is that it makes originality visible and measurable. Through OIQ scores and archetypes, leaders can see how individuals think with and without AI, and how those patterns complement each other across a team. That insight is transformative. It helps you compose teams that avoid echo chambers, tailor training so people grow their originality muscles, and even track cultural adoption of AI over time. We’re giving organizations a heatmap of where originality lives inside their workforce, and that becomes a roadmap for building AI-ready teams that don’t just adapt to the future, but shape it.

You’ve mentioned applications for consultants and government leaders who are driving AI adoption. How could Hupside specifically support government and public sector initiatives?

In government and the public sector, the pressure to adopt AI is enormous, but so are the risks of doing so without building the right team to work with it, which can lead to sameness and overreliance. Policies, security strategies, even public trust depend on originality. Hupside helps by providing leaders with a way to assess who in their organization is thinking beyond the baseline, and who can combine AI’s efficiency with human insight.

For consultants advising on transformation, OIQ data becomes a way to benchmark progress, manage change, and guide adoption with objectivity. In short, we give leaders confidence that the humans steering critical programs are bringing something distinct to the table.

Beyond government, what do you see as the biggest opportunities in the private sector and in education?

In the private sector, the opportunity is enormous. Whether it’s product development, marketing, or investment evaluation, organizations are already realizing that AI alone doesn’t create differentiation. By embedding originality into hiring, teaming, and leadership, companies can identify value creators, protect their edge and unlock new growth. Education is just as critical. Students are growing up with AI as a constant, which means teaching them how to think beyond it is one of the most important skills we can give them. Original Intelligence should be part of the curriculum, because the future belongs to those who know how to use AI while still thinking for themselves.

Looking ahead, how do you see the role of originality evolving in a world increasingly dominated by AI, and what role will Hupside play in that future?

I believe originality is becoming the defining measure of human value. As AI takes over the routine and the repeatable, what’s left and what matters most is our ability to create what hasn’t been seen before. That’s not just a nice idea, it’s a survival skill for businesses, governments, and individuals. Hupside’s role is to make originality visible, measurable, and scalable so it doesn’t get lost in the noise of automation. We’re building the tools to ensure that as AI reshapes work and society, humans remain at the helm, leading with imagination, insight, and originality.

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