Offices in

Las Vegas
New York



(416) 520 5900

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Who We Are

Steve Sterling

Steve is an experienced media management professional whose accomplishments include many award winning & award nominated projects as well as being a co-inventor of two software patents. He works closely with start-ups as well as top 100 entertainment corporations. He has initiated, strategised and/or managed profitable results for a wide range of entertainment companies, Producers, intellectual property Creators and rights holders as well as Software Developers. He has been a key player in hundreds of productions, distribution deals, performance agreements, multi-million dollar budgets and tens of millions of dollars in revenue.

Syd Kessler

Recently inducted into the Marketing Hall of Legends, Syd draws on a respected background as a successful entrepreneur, creative marketing legend and producer extraordinaire, providing a distinctly unique perspective.

After a series of early creative successes, from Hollywood screenwriter to award- winning advertising producer, Syd started a joint venture in 1988 with John Labatt Ltd., called Supercorp. Under his leadership, Supercorp grew from $10M annual revenue to over $150M in just four years, becoming the commercial production industry’s unrivalled leader. Supercorp controlled 68% of all advertising production in Canada and and 2% of the TV commercial production business in the U.S.

Syd is also one of the “bricks and clicks” pioneers in North America.

In 1994, he created The Kessler Group to address a growing need in the advertising community to move away from the broadcast advertising model, with its inherent inability to deliver measurable results, to a new advertising model called narrowcasting. The Kessler Group secured contracts with such notable American firms as Dow Jones, Wal*Mart and US West. On the heels of this success, Syd became Co-Director of KPMG e-commerce practice in 1997.

Syd also spends his time identifying, investing and mentoring new businesses and organisations, principally in the entertainment, advertising, and insight research industries in Canada and the U.S.

He is a founding member of NABS, the National Advertising Benevolent Society, which looks after the well-being of advertising professionals, and a founding member of Kids Help Phone.

He is also a prolific author on the topic of consciousness and behaviour.

Jacob Kessler

Jacob has spent the last fifteen years as an entrepreneur in the entertainment, advertising, and technology sectors, building successful enterprises with his father, Syd Kessler. Jacob has taken on different roles in these organizations, including general manager, business and marketing strategist, creative thinker, and executive producer.

As a producer, Jacob has been involved and led over 500 productions throughout his career across multiple media, from traditional TV, radio, stereoscopic 3D, out of home, and online. He has serviced verticals like media and entertainment, retail, QSR, education, not for profit, pharmaceutical and health care, consumer packaged goods, and travel.

Through his investments, Jacob has worked with companies on projects such as Audi, Live Nation, Abbott Labs, Canadian Olympic Foundation, Spider-Man: The Musical, Canadian Red Cross, Havergal College, and Renova. Jacob was also part of the team that launched Plan Canada’s ‘Because I am a Girl’ movement across Canada.


Sterling Kessler Entertainment is a partnership of industry veterans Steve Sterling, Syd Kessler and Jacob Kessler. This winning combination is a trio of expertise bringing together a diverse track record of industry successes across:

Intellectual property development

Live event production and promotion

Intellectual property rights acquisition

Television programming


Web-based content creation

The team has core competencies in strategic planning, creative development, as well as managing multi-channel initiatives through hands-on production planning, integrated advertising and operational fulfilment.

The company currently holds intellectual property rights to a range of entertainment projects while continuing to develop its portfolio by targeting market-specific properties.

A fundamental goal of the company is to maximise value in entertainment properties by capturing viewership, ticket sales and/or user-bases thereby generating impressions and revenue.

The company can place, or vertically integrate, any entertainment IP locally, regionally, nationally and globally. Distribution channels the company has access to and can place content into include theatre and non-traditional venues, television, film and internet. Sterling Kessler Entertainment has a global reach.

The company not only creates winning opportunities for programmers, distributors or sponsors and works with its clients and partners to place those results, it can also show the way forward for content engagement across all channels of distribution. Sterling Kessler Entertainment is focused on maximising its relationships with television outlets, theatre venues & promoters, sponsors, internet channels and specialty entertainment agencies.

The company is not a consumer-facing enterprise and is applying its expertise and turn-key capabilities to entertainment industry companies and high level corporate decision-makers as resources to achieve well defined objectives through content distribution and audience engagement.