Obsessed with where arts and computer science collide in business, Jason Hargrove was 15 years old when he founded his first startup, a digital t-shirt design and silk-screening company operated out of a business program in his high school. In the blink of an eye two decades passed.

Caught up in the first dot-com boom, bust, and all manner of opportunity, Mr. Hargrove built his technology and digital media career around the world. At first: Edmonton, Vancouver, and Seattle. Then Toronto, Montreal, and New York. Eight months in Cannes, France. Remote gigs in a half-dozen U.S. cities in each major area of America. So many squads, and hypotheses-driven initiatives. Big brands including a number of NHL teams, Intel, IBM, Cisco, Nokia, U2, Tag Heuer, Accenture, Chaotic Moon, and the RCMP. A number of national companies and startups.

Having founded two boutique digital agencies in the 2000s, Mr. Hargrove wore a number of business, technical, and creative hats; working closely with many CEOs, founders, marketing directors, and production teams in the conception, development, and release of a variety of products. Though these service businesses were not profitable, and the work was undertaken at great personal expense to Mr. Hargrove as an individual, by most measures they were valuable formative experiences. His roles on projects during this time were primarily Full-stack Engineer, Designer, Creative Director, Brand Strategist, and CEO. Supportive roles he undertook included Sales, Project Manager, Sales, SEO Strategist, Copywriter, and Photographer. Client types included corporate, government, education, police agencies, non-profits, collectives, startups, individuals, passion projects, and fashion weeks. During this time Mr. Hargrove became very active in social media as a Digital Strategist and Content Creator; among the very first in his home market to advocate social media as a channel for brands.

In 2010 Mr. Hargrove took a hiatus from full-time tech, when during the G20 riot in Toronto he had photography published by the mainstream media internationally. CBC News provided the largest push. In the following two years Mr. Hargrove worked as a tech-oriented photojournalist at world fashion weeks and film festivals, advocating social media distribution and the Creative Commons. During this time, Mr. Hargrove participated in a short film production that was presented at Film Festivals worldwide, including TIFF Kids and Cannes. During the latter he was also kept busy as a fashion photographer, attending various fashion events and the official photographer at Fashion Week Cannes hosted by The Jackson Family. He found this work exciting but not challenging, so he returned from France in order to start exploring a venture-focused Research & Development program again.

To kickstart this phase Mr. Hargrove joined the Centre for Social Innovation, a shared-space for social entrepreneurs with hubs in Toronto and New York. "People who are changing the world." During this time he worked with a small team to produce a variety of technologies for media distribution and social media management, with a fashion-media focus. During this period he also served as a Senior Full-stack Architect and Engineer, building apps in Node, Angular and React with a number of startups, digital agencies and an international financial services company. A highlight role with a Swiss watch manufacturer saw him participate in the first edition of a luxury digital watch product, released worldwide.

Presently Mr. Hargrove is investing his days in the financial district of The 6ix (Toronto) working in Artificial Intelligence and bot software with a team of five in Toronto, NYC, and Chicago. His 2016 R&D focus featured a scalable platform for building worker bots and chat bots; and his team has since been kept busy building bots on a variety of channels. Slack, Twitter, Messenger, Instagram, Flickr and many more. They are presently exploring the use of A.I. in a variety of business applications intended to augment workers, increasing their output productivity, with equal or less human input.

Join Mr. Hargrove on Twitter: @jasonhargrove

Above: "Unttld" collection at Montréal Fashion Week. Photography by Jason Hargrove