A version of this article previously appeared Forbes.
In my capacity as a Professor of Practice at UC Santa Barbara, I was asked by the Student Association if I would consider interviewing rapper, fashion designer and entrepreneur Tyler The Creator.
I was flattered to be considered, but Tyler’s Manager, Christian Clancy, wisely thought better of it and requested a more hip and informed Professor to conduct the interview. This reprieve allowed me to attend the event as an observer, freeing me to get schooled by Tyler, right along with the students.
The event sold out within minutes, despite the venue holding over 800 students. I’ve never seen students show up early for anything, but the unassigned seating caused the house to fill to capacity, thirty minutes before Tyler took the stage. Despite the electric atmosphere, Tyler was relaxed, sincere, humorous and characteristically profane, from start, to finish.
If you’re not familiar with Tyler, you can check out Yonkers, which has over 98 million views on YouTube. You can also review his GOLF WANG fashion line, which Tyler plans to eventually expand to include furniture and other home goods.
7 Entrepreneurial Life Lessons
No recording devices were permitted and, out of respect to Tyler, I didn’t take notes while he spoke. However, I did contemporaneously capture my thoughts later that evening. Thus, the statements below attributed to Tyler are paraphrased from my imperfect short-term memory. In all cases, I have diligently attempted to accurately captured the spirit of his comments.
The following startup lessons are those which stood out to me, though they hardly capture the full extent of Tyler’s spirited, 90-minute talk.
Be Specific – Early in the evening, Tyler was asked to give some general advice to the students. Instead, he joked that the question was too vague and from there he pivoted to a discussion about the importance of knowing what you want and then clearly and specifically articulating your vision to your team.
He gave an example of how he directs musicians in the studio with precise language, to ensure he gets his desired results. He noted, “it may not make you popular and it isn’t easy,” but not compromising when articulating your vision will always result in a more satisfying result.
Float Between Diverse Groups – Tyler stressed the benefits he has derived from being a member of groups that typically don’t interact. For instance, he shared that, “In High School I was friends with the white skaters, the black rappers and the nerds.” He took something away from each of these groups and amalgamated them into his designs and music.
The importance of diverse relationships is especially true for entrepreneurs, as breakthrough ideas typically arise when small hunches from disparate sources are combined into something new.
Get Out – Tyler was asked about his hometown of Hawthorne, California and he responded, “<expletive> Hawthorne. I hated that place. Unlike most of the people I grew up with, I got out.” Tyler went on to encourage the students to not let their backgrounds, disadvantaged or otherwise, impede fulfilling their dreams.
Fearlessly Solve Problems – Tyler attributed some of his success to his lack of fear, saying, “I’ve never been embarrassed or afraid. If I meet an obstacle, there always a way to go over it, under it or blow the roof off it.” He went on to say that he’s happiest, “solving problems” – challenges are just problems that have yet to be solved.
Don’t Get Stuck – Tyler was asked to critique several current rap artists, which prompted him to give an honest, though a bit harsh, critique of several iconic rappers whose latest releases have pretty much sucked (don’t worry Clancy, I won’t spill the beans on who Tyler trashed).
He then described how he consciously iterates his fashions, persona and music. “I don’t like the word ‘brand,’ because it makes me think of a bunch of people sitting around a table… but I (proactively) do things to avoid repeating myself.”
Embrace Failure – Tyler noted that because he is always innovating and diving into new experiences, it’s inevitable that some endeavors will not live up to his expectations. Tyler expects such setbacks, noting, “If I fail, I move on. That’s it.”
Relish Help – Tyler described several instances in which he pursued a new interest, despite his lack of experience. For instance, when he began designing shoes, his initial drawings were so amateurish that his then-current shoe sponsor grin screwed him. Rather than telling him that the drawings needed to be revamped, the shoe executives placated him with flattery, without putting in the effort required to make his designs production-ready.
Unsatisfied, Tyler dropped the unhelpful brand and was delighted when his new shoe partner corrected his design errors and brought them to the market. His shoes retained their unique silhouettes, but they were also functional and could be economically manufactured at scale.
The Teacher As The Student
I was impressed, though not surprised, with Tyler’s curiosity, intellect and candor. However, what struck me most was his genuine desire to connect with the students. With nearly each student question, Tyler asked one or more of his own, often holding an extended conversation with a star-struck student. In one case, a student exclaimed, “I can’t believe I’m standing here having a conversation with you!”
In the end, I’m confident Tyler learned as much as the students. At 27, he has an incredible future ahead of him. I hope he continues to connect with young people in similar forums and I look forward to cheering on his future entrepreneurial pursuits.
Follow John’s startup-oriented Twitter feed here: @JohnGreathouse.
Image credit: The Author