One of the big themes at Roadmap 2014 was the integration of design and technology. Speakers discussed everything from how designers and developers should work together to whether technical restraints hurt or help the design process.

Tim McCoy, the director of product design at Pivotal Labs, gave a brief presentation Wednesday on the history of technology and design butting up against each other. He went through a list of designers and companies in the last 600 years who grappled with the space between the two. Here are some of the most compelling examples:

1. Frank Lloyd Wright: Wright was an experimental designer who would frequently release design-focused structures that didn’t always hold up. He was loath to compromise his vision for practicality. At one point, Hib Johnson, president of the company Wright worked for, decided to persuade the architect using a hands-on example — he asked him to reach for something…