Dana Hawthorne: Building Companies, Betting on AI, and Pushing Through Self-Doubt

What does it really take to build a company, take risks, and keep moving when self-doubt shows up?

In this episode of the Mile High Success Podcast, Nick Elder sits down with Dana Hawthorne, founder of Modernize and a longtime technology entrepreneur. Dana has built three technology services companies, successfully exited two of them, and grown Modernize to around 80 people.

Dana shares how his career started in recruiting and how asking questions helped him learn the technology business from the inside. He talks about the mentors who shaped his career, why relationships have played such a big role in his success, and why entrepreneurs need to understand what they are good at—and hire people who are better at everything else.

Nick and Dana also dive into artificial intelligence and where Dana believes the technology is heading. Dana explains why privacy, security, and control of company data could become much bigger concerns as businesses adopt AI. He also shares the work being done through Modernize and Deployed around private AI systems and regulated industries.

The conversation gets personal as Dana talks about one of his biggest challenges: self-doubt. His approach is simple—keep moving. Dana believes entrepreneurship requires taking ownership of outcomes, becoming comfortable with risk, and continuing to push beyond your comfort zone.

They also discuss the difference between being an entrepreneur and being a leader, why Dana considers himself a “zero-to-one” builder, and why great mentors can change the direction of a career.

Dana closes by sharing why he remains optimistic about technology, skilled people, and the opportunities ahead.