From indie cred to legal disasters — this episode goes deep into the real stories behind some of Canada’s most iconic music moments. Jonathan sits down with Mark DiPietro (DSK, Teenage USA, Song Corp) to talk about the wild ride of managing artists like Len, dealing with explosive fame, and the career landmines most people never see coming.

They unpack:

The bizarre rise of Len and what happened after

The value and illusion of “indie credibility”

How artist relationships can make — or break — your label

Why The Weeknd succeeded and Song Corp collapsed

The importance of mentorship in a chaotic industry

And how some wounds in music take decades to heal It’s nostalgic, insightful, and sometimes absurd — a must-listen for anyone trying to understand the Canadian music industry from the inside out.

🎙 Full episode out now on YouTube + all podcast platforms.

Chapters:

02:53 The Music Business Journey Begins

06:08 The DSK Connection

08:48 The Rise of Len and 'Steal My Sunshine'

11:59 The Complexities of Artist Relationships

14:48 Navigating the Music Industry's Challenges

18:13 The Impact of Indie Cred

21:13 How Music Consumption has Changed

26:59 The Aftermath of Legal Battles

37:54 The Aftermath of Fame for Artists

41:31 Mentorship and the Journey of Teenage USA

42:57 The Evolution of The Weeknd

44:40 Defining Success in the Music Industry

45:40 Navigating the Challenges of Record Labels

47:39 Lessons from the Fall of Song Corp

51:41 The Journey of Selling and Regaining Control

01:07:44 Reflections on the Music Industry and Personal Growth

01:12:27 The Nickelback Phenomenon and Closing Thoughts

 

#IHateSimkin #MarkDiPietro #Len #StealMySunshine #CanadianMusic #MusicIndustry #IndieMusic #TeenageUSA #TheWeeknd #ArtistRelations #Nickelback #604Records #MusicPodcast