Lessons from 24 Year Old Kanye

January 21st 2021

I never really thought of myself as an entrepreneur. I wasn’t that yung hustla flipping lollipops to second graders.


I cared more about sports and having a good time with friends. But as I began to feel the realities of being a salaried employee, the idea of becoming an entrepreneur started sounding realllllly nice.

I wouldn’t have a pointy-haired boss telling me what to do.


I wouldn’t have to show up at the office at a certain time. I wouldn’t have to work on uninspiring projects.

But entrepreneurship is really damn hard.

I quit my job three months ago and have spent a lot of time thinking about what to do next. I have a document filled with ideas on what to work on. But I’m overanalyzing the shit out of everything.

“How am I going to get customers?”

“How should I build this?”

“How will it make money?”

The hardest part about entrepreneurship isn’t marketing, sales, technology, or any other stuff you read about on blogs, podcasts, and Twitter.

The hardest part is managing your own psychology.

Entrepreneurship seems so glamorous based on social media, TV, and movies, but I’m starting to realize that the reality is more like this:


The novelty of being an entrepreneur started to wear off and I faced this “oh shit” moment where I realized how hard this is going to be.

I’ve had a handful of days where I’ve considered going back to a full time job. It would be so much easier! I could just grab some coffee, sit at my computer, write code for a few hours, go to a meeting or two, write some more code, and make a damn good living.

But in moments like these when I doubt myself, I try to think back to what appealed to me about entrepreneurship in the first place. The freedom. The creativity. The ownership.

To keep me motivated, I love reading about how successful entrepreneurs navigated through their own trough of sorrow. What was going through their mind? What challenges did they face? How did they stay inspired?

A few days ago when I was feeling a bit down, the YouTube algorithm gods recommended an interview with Kanye West in 2002.

In the interview, Ye was still two years away from releasing his first album - The College Dropout - which was nominated for 10 (!) Grammys and made him one of the biggest artists in the world.

In this early interview, I see a lot of myself in him. A young man trying to make a name for himself, but faced with doubters and personal challenges.

I recommend watching the entire interview so you can feel the type of energy and confidence Ye had as he was coming up. Here are some of the lessons that stuck with me.

Sometimes you gotta do grunt work

When Ye was an up and coming producer in Chicago, he talks about how he had to make beats for people that didn’t have much talent. He dreaded these sessions. But he had to secure the bag💰

At one point, Ye was in the studio with one of these mediocre rappers when he got a call from his friend Just Blaze, a fellow producer. After a few minutes of catching up, Just Blaze said he had to go because he was starting a session with Busta Rhymes - one of the biggest artists at the time.

Ye remembers thinking to himself: “Just Blaze is over there makin’ beats for Busta and I’m over here makin’ beats for busters!”

In this day and age, we’ve been programmed to expect instant gratification through likes on social media and access to streaming services with practically every song, movie, and TV show ever made. But sometimes we gotta do stuff we don’t really like. Whether it’s a job or developing a new skill.

During this time, the important thing is to focus on mastering your craft and build a solid foundation so you can take risks in the future. As you hone your craft, you’ll be in a position to start taking bets on yourself.

Take bets on yourself

When Ye was 22, he had producer friends in NYC telling him he should move there. For the longest time, he resisted. He was comfortable at home in Chicago. But once his music production business fell apart and he was evicted from his apartment, he saw it as a sign he needed a fresh start.

Once he arrived in NYC, his producer friends brought him to the recording studio where he started making a name for himself. At one point, Jay Z was coming in for a session with another producer but overhead some of Ye’s beats. Two weeks later, Ye produced half of Jay Z’s next album, The Blueprint.

After The Blueprint released, Ye began getting asked to make beats for all the hottest artists.

But his dream wasn’t to be a producer. His dream was to create his own album. After getting his first record deal, Ye stopped producing for artists to focus on his album. He talks about how he left a ton of money on the table which was tough since he still hadn’t really made it yet.

Yet, he took a bet on himself. Worst case, if his album flopped, he knew he could go back to producing beats.

Many times, taking a bet on yourself isn’t as risky as you think. Especially if you’ve built rare and valuable skills. In fact, if you take a few months or years to work on your own projects, you’ll probably be more employable in the future. Many employees lack the perseverance, resourcefulness, and generalized skillset it takes to be an entrepreneur.

Combine skills

Ye doesn’t describe himself as a hip hop artist. Or a music producer. Or a fashion designer. He describes himself as a Creative.

Making beats, writing songs, and designing sneakers are just channels for creative expression. At the time Ye was coming up, producers and artists stayed in their lane. You rarely saw a producer try to rap or an artist whip up their own beats.

Ye didn’t care.

While producing beats for an artist, he would start rapping for them. Most of the time they told him he was whack and laugh in his face. But he kept sharpening his craft. Over time, Ye got better and eventually scored a record deal for his first solo album.

There are two main ways to become world-class at something. One path is to become the top 0.01% in the world at a single thing. This takes years of specialization. Think scientists, doctors, lawyers.

Alternatively, you could become top 25% in multiple skills and combine them in a unique way. Ye combined skills in production, writing raps, and eclectic taste in music from rock to soul which ended up creating one of the most iconic albums of all time.

Combining skills in a unique way is also how most entrepreneurs become successful.

I know that I’m never going to be a top 0.01% software engineer. I don’t geek out on the latest technologies or read Hacker News religiously. But I can build fairly complex apps in just a couple weeks. I also enjoy learning about business, design, and product strategy.

Given my broad interests, I realized I was never going to maximize my potential by being a code monkey. That’s why I’m going the entrepreneurial route and creating my own job.

Instead of being the best at what you do, be the only one that does what you do.


The purpose of sharing these stories is to show that accomplishing anything significant is really damn hard.

You’re going to face challenges. You’re going to doubt yourself. You’re going to want to quit.

However, by studying the greats, we gain the wisdom, patience, and resilience needed to navigate our own troughs of sorrow and make it to the promised land.

Moar knowledge 🙇‍♂️