About this episodeJesse Reyes details her journey from a working-class immigrant family in Toronto to becoming a successful song…AI summary
Jesse Reyes details her journey from a working-class immigrant family in Toronto to becoming a successful songwriter and artist, highlighting the critical role of resilience, mentorship, and seizing unexpected opportunities. Her career breakthroughs were driven by overcoming industry gatekeepers, collaborating with high-profile artists like King Louie through sheer initiative, and securing a publishing deal with BMG after persistent courting. The narrative emphasizes that success in the music industry requires not just talent but the ability to navigate social anxiety, maintain creative authenticity, and balance ambition with personal well-being.
Key takeaways 6
Immigrant hustle as a foundation: Reyes attributes her work ethic to watching her parents work multiple jobs and hustle, which made her 'more willing to find a way when it didn't seem like there was a way' and more willing to grind.
The power of mentorship and community: Joining the 'Remix Project' was a turning point because it provided access to mentors and peers living off their art, making the dream feel attainable rather than distant.
Overcoming gatekeepers through resilience: A dismissive comment from a gatekeeper in Florida nearly made her quit, but she realized that letting one negative experience end her career would be illogical given her previous struggles.
Initiative in collaboration: The collaboration with King Louie happened because Reyes overcame social anxiety to ask him to jam on a balcony, then immediately engineered and sent the track that night to strike while the iron was hot.
Organic growth over forced strategy: Reyes notes that her initial momentum came from 'throwing stuff to the wall' and being open to any opportunity (open mics, auditions), which created an organic groundswell rather than a calculated plan.
Financial literacy in ownership: She argues that selling masters can be a valid financial strategy if one understands money management and investments, rather than holding onto assets solely for the sake of ownership.
Notable quotes 5AI-generated: wording and quote attribution may be wrong. Use the play link to verify.
“If I've gone through all the other [ __ ] that I've gone through and all the auditions and all the interviews for one night to be the night that makes me quit ain't really the vibe.”
▶ 13:01Reyes explaining how she overcame the demoralizing experience with a gatekeeper in Florida, choosing resilience over quitting.
“Having someone in front of you that's like oh [ __ ] your skin looks like mine you bleed just like me you breathe just like me and you're able to do it it made everything so much more attainable.”
▶ 15:10Describing the impact of mentorship at the Remix Project, where seeing relatable figures succeed made her goals feel realistic.
“You can't let it waste you can't let it you can't let it pass like this was given so I just burst out and I'm like you wanna you wanna jam.”
▶ 17:57Reyes describing the moment she overcame social anxiety to initiate a collaboration with King Louie, leading to the song 'Living in the Sky'.
“Honesty without the Quorum is [ __ ] mean... I don't do names on purpose because I am not gonna say I'm this way and honestly at the expense of someone else.”
▶ 31:40Reyes discussing her approach to songwriting, balancing brutal honesty with respect for others by avoiding specific names.
“Ambition's not a bad thing as long as I'm not a dick ambition's not a bad thing as long as I'm not a maniac and I can still balance that and consider myself my own friend.”
▶ 35:57Reyes reflecting on her current mindset, finding peace and contentment without sacrificing her drive.
Chapters & Sections (24)▼
0:00Childhood Influences on Creative Ambitionschapter3
0:00Overcoming Adversity to Achieve Creative Success
2:03Overcoming Adversity through Creative Pursuits
4:16Challenges of Pursuing a Music Career
7:29Immigration and Family Visa Challengeschapter2
7:29Immigration and Family Visa Challenges
10:23Overcoming Creative Setbacks and Finding New Opportunities
11:44Overcoming Self-Doubt and Industry Gatekeeperschapter2
11:44Overcoming Self-Doubt and Industry Gatekeepers
13:39Finding Inspiration and Turning Point in Music Career
15:55Unlikely Collaboration and Overcoming Social Anxietychapter3
15:55Unlikely Collaboration and Overcoming Social Anxiety
18:09Songwriting Process and Creative Freedom
19:27Navigating Creativity and Self-Expression as an Artist
21:20Securing Music Publishing Deal with BMGchapter2
21:20Signing with a Major Music Publishing Company
23:03Artist's Career Evolution and Creative Growth
25:20Releasing Music During a Pandemicchapter2
25:20Releasing Music During a Pandemic
27:59Balancing Success and Mental Health Struggles
29:39Overcoming Vulnerability and Emotional Healing Processchapter3
29:39Overcoming Vulnerability and Emotional Healing Process
32:15Effective Leadership and Team Management Strategies
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