There are musicians who dabble in business after experiencing some success, and then there’s Peter Jackson.

The Canadian hip hop artist has created a silo all his own over the years, putting on a clinic in what it means to be a businessman in an industry that can hold you down as efficiently as it once propped you up. In fact, Jackson could probably teach the Canadian music industry itself how to build a foundation, or how adding a personal touch to business isn’t the kiss of death we tend to think it is.

Or maybe the key to Jackson’s success is that he’s one of few personalities who has found a way to befriend the people he works with, or puts in the spotlight.

Blackballed welcomes hip hop artist/entrepreneur Peter Jackson to the show @peterjackson905 @jamesdifiore https://t.co/N2FDwur4Eg

— James DiFiore (@jamesdifiore) May 11, 2023

Hip hop has had its fair share of moguls, and most of those people are American. Drake is obviously a Canadian success story, but Jackson has forged such a unique path for himself in the game that he really is a standalone product. He speaks openly about how mixing business with friendship has been a key ingredient to his success, a complete departure from where most business-savvy people reside. That old adage is probably even more true in the music industry, where friends often have expiry dates that kick in the second you put your boy on a flyer.

Jackson is led by his instincts and his love for the music of the artists he books through his company, International Touring Agency. He often connects with these artists before heading out on tour, and sometimes will collaborate with them as well, creating a business model that virtually no other touring company could manage. He doesn’t shit where he eats; he designs a landscape where dining with his creative partners actually makes the most sense.

The other aspect of Jackson’s career is his loyalty to family and close friends. In a business that often takes you on the road for months at a time, Jackson has prioritized his love for his wife and kids in a way that feeds his success, rather than limits it. He describes himself as the greatest hockey dad ever, and was influenced by his mentor to keep his family front and centre when making moves.

That mentor was Sheldon Moore, AKA DJ S-LUV from the legendary hip hop/jazz group, The Pocket Dwellers, and one of the game’s finest producers/engineers. Sheldon passed away last year, leaving a massive hole in hip hop culture, especially when it came to young, hungry artists. Jackson and Moore worked together for 15 years, and the entanglements between their business and personal relationship became some of the best memories Jackson has of the late producer.

This is for my homie Sheldon Moore, aka S-Luv, DJ/Producer of the Pocketdwellers and the first Jedi I ever knew.

RIP Sheldonhttps://t.co/J6olnLQOe6

— James DiFiore (@jamesdifiore) August 5, 2022

On the Blackballed podcast, Jackson recalls the story of how Moore’s daughter was the flower girl for his wedding. The two rode together as the only passengers in the Rolls Royce that brought him to the church, a testament to his respect for the youngster that stemmed from his respect for her dad.

This interview opened my eyes a little, reminding me of the importance of stopping to appreciate the people we choose to be a part of our extended family. It also made me respect Jackson not just as an artist, but as a human being navigating difficult waters and showing others how to do so successfully.