How a Canadian Marketer Changed His Life With a 20 Year Side Hustle

Leland Dieno is a career Digital Marketer starting his career working in IT Systems for one of Canada’s largest grocery chains. He transitioned into a technical marketing role and joined the launch team for Canada’s first online delivery and pick up grocery solution in 2014. From there he went on to manage the digital strategy team at a University managing their web development, digital advertising strategy, videography and social media.  He’s also built and scaled one of Western Canada’s largest Marketing Agencies as their Vice President before exiting to focus on his own business.

In the early stages of his career, he was frequently asked by friends and family to assist with website development or even more so; random technical projects to assist with their business operations. He quickly developed a passion for digital strategy, technical project management and developing solutions. He was an early adopter of building solutions online and utilising internet 1.0 to generate income. In highschool he was featured on CTV’s “The National” with 3 friends for building one of Canada’s first hosting companies, and offering web hosting solutions to high school students at no cost. From there he went on to build websites on a traffic based model to earn monetization income.

Leland’s approach to every business he’s been involved in has been to be conservative fiscally and to only scale in small steps. He accounts this to growing up in a lower-than-middle class financial situation and always being mindful of ensuring he has a roof over his head. He would be the first to admit that his reluctance to take big risks is probably why he never achieved his “Mansion on the hill” dream, but he would also say that for a guy who came from where he did, he’s quite happy with his life. A former hip hop artist and independent hip hop label owner who toured Europe, turned single full time father who manages digital teams for large organisations and is a partner in several tech-startups and businesses has fulfilled most of his bucket list items; still with a long way to go to keep the hustle alive. At 39 years old Leland has owned and managed a digital consultancy, a janitorial company, a hip hop label, a pro-fatherhood brand, and is a partner in a successful wallpaper company, a drone training institution, and a social media service agency. 

Since he entered the workforce in 2001, he has run Dieno Digital Marketing Consultancy as a side-of-his desk, evening and weekend side hustle. The business operated from 2001 to 2017 solely to supplement his income. As he focused his 9-5 on digital strategy and managing large teams for some of Canada’s prominent brands he still worked evenings and weekends supporting businesses with web development, digital advertising and technical solutions. Between 2017 and 2022 Dieno Digital scaled to employing 3 full time staff members and 5 part time all while Leland still maintains it as a part time side hustle maintaining his commitment of 10 hours per week to the business. Anyone who has met Leland would say that he is “systems minded”. Even though he is a creative, and very passionate about technical problem solving; the business would not have become what it is today without having very strict standard operating procedures and incredible team building.

Leland’s next venture for Dieno Digital is Scale Freelancing an online learning portal for freelancers to learn the operational and sales tactics he learned to turn their freelancing side hustle into a consistent brand and business.