From Military to PropTech: How Helix Intel’s Founder Used Marine Corps Lessons to Scale to 100k Buildings

At 18, Jon DeWald found himself in an unexpected situation. “I signed up in legal administration… and 911 happened, and they switched a lot of the Marines to combat infantry battalions,” he shared in a recent Category Visionaries episode. This sudden pivot from aspiring lawyer to infantry soldier in Iraq would later shape his approach to building one of the fastest-growing companies in PropTech.

The Military Mindset: Flexibility as Foundation “I think the thing that was the most rememberable to me is to be flexible,” Jon reflects on his military service. This lesson proved invaluable when building Helix Intel, as the company’s trajectory would take several unexpected turns.

From Manufacturing to Insurance Like his military career, Jon’s entrepreneurial journey didn’t follow the expected path. With experience running a federal dealership at Ingersoll Rand, one of the world’s largest air compressor manufacturers, he initially aimed to solve manufacturer-customer connectivity issues. However, when Munich Reventures discovered their pre-seed pitch deck, everything changed.

Adapting to Market Intelligence The ability to adapt quickly – a skill honed in the Marines – enabled Jon to recognize and seize this opportunity. The insurance industry was facing a crisis: claims were outpacing premiums at an alarming rate. Rather than sticking to their original plan, the team pivoted to address this larger market need.

Building Cross-Functional Teams Military experience taught Jon the importance of diverse skill sets within a team. “This is my first traditional software business, and I’ve had to learn quite a bit about product development, product management, software development,” he admits. This humility and willingness to learn led him to build a team that complemented his experience gaps.

Rapid Deployment and Scaling The results speak to the effectiveness of this military-influenced approach. “So far this year, we’ve added over 100,000 buildings onto our platform,” Jon shares, compared to just 15,000 the previous year. This dramatic scaling came through strategic partnerships with insurance companies, demonstrating the military principle of force multiplication through alliances.

Speaking Multiple Languages Just as military success requires communicating effectively across different units, Jon emphasizes the importance of speaking multiple industry languages: “They speak utility, right? Insurer speak insure property. Speak property. And having the ability to understand and communicate value to each one of them is instrumental.”

Mission-Driven Leadership The military’s emphasis on clear mission objectives influences how Jon approaches business strategy. “We’re building operating software that brings multiple ecosystems together under one platform,” he explains. This clear vision helps align team efforts and attract strategic partners.

For B2B founders, Jon’s journey offers valuable lessons in adaptability and strategic thinking. The same flexibility that served him in the Marines has enabled Helix Intel to identify and seize opportunities in traditional industries. By applying military principles of adaptability, clear communication, and strategic partnerships, they’ve created a new model for scaling B2B technology in resistant markets.

The result? A company that’s not just growing rapidly but reshaping how traditional industries approach risk management and maintenance. As Jon puts it, “We’re in this unique space where we don’t compete with anyone. We’re really a new business model and a new ecosystem that collaborates.” It’s a testament to how military leadership principles can transform business strategy in unexpected ways.