We all dream

I was a public school kid, so I was surrounded by hip hop. The first cassette tape I can remember having was It Takes a Nation of Millions by Public Enemy. I thought DJing was the coolest art form, and I got turntables in 1991 and locked myself in my room. I’ve always been somebody who wants to be great at what I do and put the time in to master a craft. Every night I would stay up till the early hours of the morning learning to scratch, watching battle DJs to take inspiration.

But I always had a feeling that the value is in originality and having your own thing. So I decided to start performing at nightclubs. I was really young when I started. A lot of other pros had predefined sets. They knew the music they were going to play throughout the night, but I would come with ten crates of records and not know where I was going. I would follow the crowd.

No, I did, but I was following my gut. I find this whole “follow the data” or “follow the research” thing to be so backwards sometimes. Nothing profound was built off of research in the classic sense. I have my antenna up about what it is that moves people, but I follow my heart, instinct, taste, imagination. It was night after night of doing these clubs where I started to become one with the audience.

I started my first company at 21, but it was in the hip hop space. All of my pursuits have followed a thread of what I’m passionate about, and what moves me at the particular time. Now I am moved only by the feeling of making things that are meaningful, helpful to people in a true sense, not in some corporate distorted sense.

We built Acorns because the playing field remains uneven, and everyone should have equal access to the real tools of wealth making: from long-term investing, diversification, and dollar-cost averaging to compounding, financial education, and lifelong family wellness.

In my 20s, it was hip hop. It was a product development and marketing agency focused on young adults. It was a music company. I wrote a book called Chasing Cool that was an exploration into what creates magnetism in culture and among consumers. We interviewed 75 people who had created something magnetic in every kind of field. I would spend a couple hours with Michael Lang, who started Woodstock, or Ahmet Ertegun, who founded Atlantic Records, or Richard Meier, the architect, or Tom Ford. People who were perceived as “cool” by a large following. And the question is why.

I co-wrote the book with the person who ran Barneys. I spent four years working on this with him, and I learned so much from him about taste, simplicity, merchandising. Everything is merchandising to some extent. You’re romancing somebody through a journey to a destination, and it’s no different than moving someone through a store.

One of the biggest takeaways from the book was that what’s happening in corporate America is often chasing, but what leads to wonderful outcomes is the pursuit of an internal feeling and your own sense of taste. And above all things, you trust yourself.

It was promoted in my household growing up, particularly by my mother. I can immediately transport myself back to this moment where she gave me a book of Albert Einstein quotes, bookmarked to, “Few are those who see with their own eyes and feel with their own hearts.”

But it’s a really hard thing because many people are told certain things as children. My wife and I started an art organization called Give Kids Art, and the message is “Create Fearlessly.” The founding ethos is based on another quote, this one from Picasso: “Every child is born an artist. The problem is how to remain one as we grow up.”

I think everybody is creative. We all dream, and dreams are magnificent. Every night you fall asleep and you become a producer, a director, a director of photography, a writer, an actor. You’re creating full feature length films in your mind every night. These are miracles. So when somebody says to me they’re not creative, I say, “Do you dream? You’re probably just not in touch with your creativity. So you need to pull that out, whatever is cutting you off from that inner child.” Back to the point - every child is born an artist.

Kids ask, “Why are things this way?” More often than not, impatient adults respond with, “Just cuz. Stop asking so many questions.” Kids also break things. But kids break things because they’re experimenting. They’re trying to learn their way.

There’s a wonderful book about how animals experience the world, An Immense World. I think of it as a metaphor for what happens to kids. Dogs smell history. They experience smell as a chronological record of everything that happened in that spot. So when you pull your dog away from smelling, you’re breaking their natural instinct, their joy. I think the same thing happens to kids when they’re told, “Don’t drop that. Don’t break that. Stop asking questions.”

Maybe it leads to more imagination, because you don’t have to be confronted by “just cuz.”

Creativity, in many ways, is the ability to synthesize things into something your own. So if you have that foundation, you can access all of this amazing information and inspiration, but that’s just an input or an insight. I don’t think anybody should be treating AI as a replacement for their own instincts. It’s really hard to believe the human propensity for imagination would be replaced.

I’m drawn to people, and I’m fascinated by magnetism. I find myself going down many YouTube rabbit holes around people, just observing. I’m fascinated by Conor McGregor, the MMA fighter. Not because I like MMA (I don’t), but I’m just fascinated by him as a personality. I’ve watched every interview he’s ever done. There is a confidence and a self belief that’s infectious. This man truly believes in himself, and he’s also a great improviser - he’s as quick with his words as he is with his fists.