The Wild Story Behind Len, Lawsuits & The Fall of Song Corp | I Hate Simkin X Mark DiPietro #6

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