Canadian Side Hustler builds businesses with sweat equity model

builds businesses

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 and higher education. 

A single father who founded one of the biggest online fatherhood initiatives, No Deadbeat Society, Leland has been working in some fashion since he was 14 years old. Whether it was supporting his father’s furniture business after school, or starting a Web Hosting business that garnered national attention in high school he was always motivated to create and build businesses.

Leland is a digital strategist and technical project manager at heart. He is currently the founder and a partner in several businesses.

Dieno Digital Marketing Consulting; is a Digital Marketing Services company that supports companies with complex web development and digital strategy. Dieno Digital has supported some of Canada’s largest brands and often works with SMBS and startups.

Coastal Drone Co; One of Canada’s first online drone certification training schools and platforms to train over 20,000 Canadian drone pilot students to date.

HQ Social; is a Social Media Management company offering affordable, content-focused social media activation and execution for small businesses.

Black Mango Design Co; is a new design startup focused on providing traditional design services and copywriting services for businesses.

West Coastal Legal Assist; is a paralegal services company that supports lawyers and law firms with remote, sub-contracted paralegal services.

Otto Studio; is a premium peel-and-stick vinyl wallpaper company focused on renter-safe wallpaper.

No Deadbeat Society; is an online peer-to-peer coaching platform for single fathers in North America.

Dieno Educare Foundation; is a registered Canadian Charity that supports childcare initiatives and support in developing countries.

Canadian oilmen drill the government for aid(Opens in a new browser tab)


Leland also sits on several nonprofit and charity boards or committees.

Leland uses a sweat-equity model to earn ownership

Leland quickly developed both technical and marketing skills at a young age, and while working with one of Canada’s most entrepreneurial groups he discovered a sweat-equity play that earned him ownership in several companies. While the businesses he is supporting and operating are not generating millions of dollars, it’s provided him with an opportunity to immerse himself in several verticals and sectors.  

Sweat-Equity in business is fundamentally trading labor for equity (ownership percentage) of a business.

This is an investment and a risk. Leland has founded and worked with long-time friends and business partners creating businesses over the years that have failed. He has also been a part of profitable ventures. The goal here was never to get wealthy from it, but to create a lifestyle and environment for himself where he is constantly solving business problems and being creative.

It’s an interesting model; and one that he strongly recommends for young entrepreneurs who are looking to be a part of, and learn how businesses are built, launched and scaled.

Savvy Chic Designer Joanna Sherrow Shares the Secrets To Sales-Converting Web Design(Opens in a new browser tab)

How to find sweat-equity opportunities

If you have a specific skill set, you may be surprised at the opportunities around you and the potential for partnerships or sweat-equity ownership in businesses. Especially for freelancers. Freelancers that are working remotely continually have clients coming to them for support. While paying clients is great, and needed, there is also potential for joining forces with other entrepreneurs and launching businesses. For example, a freelance graphic designer can devote a solid amount of start-up hours to a tech company for equity in the company and then transition into an ongoing advising role that requires only a few hours a month of work, but a lot of networking opportunities and profit sharing potential.

With this in mind, Leland created Scale Freelancing, a new training platform for freelancers to learn how to build their freelancing side hustle into an actual business through direct, affordable tactics that he has learned throughout his 20-year career.

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