Skylar Grey

Skylar Grey says she is putting out an album, and the conversation starts with one of her songs. Rogan says his wife told him she wants Grey's song referred to as "I'm coming home" played at her funeral. He calls that "a heavy thought." He then describes listening in the gym to a version with Grey on piano, which he says felt "like a solo concert," and calls it a great song attached to a "crazy thought."

The talk moves to AI-generated music. Rogan grants that "There's cool songs that come from AI," and argues that listeners will still value knowing that a person sat down and wrote a song, because that carries a connection to the writer's spirit and creativity. He says he likes some AI music because it sounds cool, but adds, "I know it's just a robot." Grey's position is more mixed. She says AI is sometimes good for certain things, but the kind of music she makes is therapeutic for her to write and comes from real feeling.

I always am writing from like a true emotion.

To show that new tools are nothing new, the speakers bring up an older vocal effect. Producer Jamie describes it as a tube like a straw: the sound travels through the tube into the performer's mouth, and the microphone picks up the result. Rogan recalls that people used to complain it was "not his real voice." He concludes that there will always be tools people use to enhance creativity. What is different now, he argues, is that AI can produce entire songs, including tracks that imitate Grey's style, and that they "sound really good." His other example is an audio-only clip of himself talking with Steve Jobs, whom he never met. He says he expects a video version to come eventually, and that fake clips already exist of him interviewing people who have never been on the show.

Yeah, we're living in a weird, blurry time. Like the lines between real and not real are getting very blurry.

Rogan compares this to the "first whispers" of the matrix closing in. His concrete evidence is that prominent news figures have reposted stories with videos that looked "straight out of a video game." People are now questioning everything, and he says they should. Grey takes a more optimistic view and calls the moment "also exciting." Rogan agrees it is exciting and fun, and adds that it is also weird.

Both speakers expect AI to make physical, human-made work worth more. Rogan points to a chimp sculpture in the studio by an artist he calls Shane Against the Machine, which the transcript describes as made with cymbals. Its value to him is that "I know a guy made that." Grey argues that imperfection is part of what makes art relatable and shows that it came from a person. Rogan describes a painting as a person's "essence" on the canvas.

value like nuance and mistakes and things not being perfect

Grey describes being "born into an extremely musical family." Her mother played in folk bands and plays Celtic harp. Her father sang in a barbershop quartet, and her great-grandmother was an opera singer. She says that at about two years old, while the family sang happy birthday to an aunt, she started singing a harmony line before she could even say all the words. She then sat in on her mother's band rehearsals and was brought on stage for small guest appearances.

Grey played her first show at six: an hour-long Mother's Day set with her mother at a library in Madison, Wisconsin. She grew up in a Wisconsin village of about 1,500 people. The duo went on to tour the Midwest, playing elementary schools, libraries and women's health conventions. She says she thinks one of their biggest shows was a Boy Scouts event with about 1,500 Scouts. She did this from age six until she went solo, which she thinks was at 12.

Grey stresses that this was small and organic, not a Disney-star career. She still earned "decent money for a kid," saved it, and at 12 bought her first grand piano. That piano is where she began writing pop songs on her own. Middle school played a part in the change. Classmates mocked the duo's songs, and she gives titles such as "we are the colors of the rainbow," "never smoked tobacco" and "my grandma slid down the mountain."

Going solo was costly for her mother, who "was not stoked." Grey explains that the duo had become her mother's career. Grey herself missed a lot of school and sometimes played six shows a week. When Rogan asks whether this caused real friction, Grey says no: her mother was supportive but had to change her whole lifestyle. Asked whether the decision was hard, Grey answers "Yes and no," and says she was so driven that doing anything else was never an option. She also knew she would not sing with her mother for her whole life. The exchange is briefly interrupted when Rogan speaks to his dog.

Grey says she hated school and begged to be homeschooled, but the family could not make that work, so she dropped out at 16.

Because I was so focused on music, I felt like I was wasting my time in school.

The trigger was her algebra teacher. Grey had not done her homework because she had played a show the night before, then aced the next test. She says she was a good student with "like a 3.9." The teacher insisted she do homework like everyone else, and when Grey explained that she had had a show, the teacher said music is not a career. Grey says this "lit a fire under my ass in a good way" and that she never went back.

Rogan calls the remark irresponsible and pushes back on it directly: people pay for concerts, and someone is on stage making the music. Grey places the attitude in a small-town Midwest culture that steers kids toward school and a good job, then corrects herself and says it is probably everywhere. She admits the comment could have pushed her the other way. A child could easily assume an adult must be right. Rogan suggests that adults eventually realize many teachers are in the job because a teacher was needed, not because they are especially good at shaping children.

Grey qualifies the criticism. She had some very good teachers, and there are "a lot of them," but the algebra teacher "was not one of them." Rogan then argues that the problem is structural.

It's hard to find someone that's really good at a job that doesn't pay very well.

Rogan's argument is that if society valued its future, it would pay teachers well and make sure they were trained in psychology and in motivating children. Instead, poor teachers go underpaid, good teachers go unrewarded, and retirees feel unappreciated and "have to fight for your pension." Grey agrees: "The whole system is so messed up."

Rogan then offers a more speculative claim, which he himself frames as going "down the tinfoil hat road." He says mass schooling was essentially designed to produce factory workers. He calls early, all-day schooling fairly recent in human history and suggests children are enrolled young because five- and six-year-olds are easier to shape than teenagers. As examples he lists single-file lines, sitting facing forward, the Pledge of Allegiance, and giving medication to children who cannot pay attention. Neither speaker cites a source for these historical claims.

After Rogan's line about medicating children who cannot pay attention, Grey jokes that she probably should have had some of that medication, and is told "Probably not." She says she definitely thinks she is an undiagnosed ADHD case, and adds that she feels "almost everybody is." This is a self-assessment, not a diagnosis. Rogan says that after discussing it the day before with a friend named Eric, he thinks it is "a fucking superpower" and not negative at all.

The speaker who goes on to describe the pattern says they check out of anything boring and cannot absorb material that does not interest them. When something does grab them, they can stay up for days, which is why they avoid video games, though the same happens with anything they love. High school felt like "torture" except when they were "fully locked in" on something. They say they once assumed they would be a fringe person who could not hold a job or take direction and would get by on odd jobs. They now credit luck and finding "some things that are unconventional."

Rogan says many children hear that music, acting, writing books or comedy is not a career, often from people who never tried those paths themselves. He gives his own example. As a boy he wanted to be a comic book illustrator, but he quit art in his senior year because of the only art teacher at his small high school. He wanted to draw comic book subjects such as Conan the Barbarian and superheroes. The teacher told him he would not make a living that way.

you're most likely going to have to do like advertisements for like diapers, like diaper ads.

Grey suggests the teacher was probably an artist who did not make it and became a bitter art teacher instead. Rogan agrees and says the students looked at the teacher's own work and found it uninspired. He also speculates, based only on the man's appearance, that the teacher "probably drank a lot." This is a guess, not established fact.

Grey extends the pattern to the music industry. She says she feels many of its experts are former artists who did not make it, are bitter, and then try to tell artists how everything should be done. Rogan agrees.

The transcript has no speaker labels, so some attributions above are inferred from context, especially for the hyperfocus remarks. Several passages are garbled in transcription, including the opening exchange about Rogan's wife and the description of the sculpture's materials. Claims about the history of schooling, teacher quality and ADHD rest on personal experience and speculation, with no cited evidence. The section also contains sponsor reads for Wayfair and ARMRA (rendered “Armora” in the transcript) that are not part of the interview, and their product claims are not covered here.