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