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Index/Startups & Founders/The Real Jason Duncan Podcast
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367. Why 95% of AI Investments Fail to Deliver Real ROI

The Real Jason Duncan Podcast · 2026-06-15 · 45 min

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Episode notes

In episode 367 of The Real Jason Duncan Podcast, most entrepreneurs believe AI is the great differentiator, the tool that will finally give them the edge. Jonathan Aberman spent decades at the center of the technology world watching that belief quietly destroy the one thing businesses actually compete on. Jonathan Aberman is an entrepreneur, investor, and innovation strategist who has helped launch more than 40 technology companies, served as the founding dean of Marymount University's College of Business and Technology, and is the co-founder and CEO of Hupside - the company building the Original Intelligence category. Forbes called him the unsung hero of the effort to bring Amazon HQ2 to Northern Virginia. Named a "Tech Titan" by Washingtonian and recognized among the Washington Business Journal's "Power 100," he has spent over two decades at the intersection of technology, venture capital, and human potential - and what he found there changed everything he thought he knew about AI. Today, Jonathan sits down with Jason for a conversation that most technology executives don't want to have.

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