Lessons Entrepreneurs Can Take From Freestyle Rapper Harry Mack

Harry Mack’s mission is to reduce human suffering by uplifting and inspiring other people with his freestyle rap.  

Harry Mack is a creative entrepreneur.

He figured out how to take his freestyle skill and create a business.

He now has live shows, building his social media following into the millions.

While not the first artist to be independent of a music label, he’s the first freestyle rap artist I’ve seen do this.

He has no hit on the radio or Spotify.

Because every piece of music he creates is original and created live on the spot.

To get a taste of what Harry Mack does, watch one of my favorite videos I’ve seen from him so far.

To give you some context, one of his ideas is called Omegle Bars.  

He hops on this website where random people connect, and he does freestyle raps for them.

Starting at 13:05, he connects with a guy that’s been drinking. A lot.

He does his standard rap for the guy (yes, it’s an incredible freestyle), but it takes an emotional turn at the 18:17 mark.

And you realize why the guy has been drinking.

This freestyle made me emotional, and it’s when I realized there was something special about Harry Mack.

Let’s rewind and learn more about Harry Mack’s Story.

How Did Harry Mack Become Famous?

To understand how Harry Mac became famous, we have to rewind to Harry at age 7.

He got into music at age 7, playing the violin.

And his musical fame began.

Nope, not quite.

The performance was a disaster, as he cried instead of publicly performing.

He never even made it to the stage.

I just wanted to show you that he wasn’t born a musical prodigy but has developed his craft and continues to do so over time.

Moving forward a few years, Harry was freestyling in middle school with friends.

Take note, entrepreneurs, he was honing his skills.

Harry Mack was also learning the drums.

In high school, he had a band, and they would have shows with hundreds of folks and sell merch.

His next step was college, where he studied jazz drums at USC.

He loved jazz drums and had professional gigs when he graduated.

But he was barely scraping by as a jazz musician.

He also never stopped perfecting his freestyle craft.

But how could Harry Mack make it as a rapper that freestyles?

There are no ‘freestyle rappers’ on the radio.

There’s no path for freestyle rappers through traditional labels.

They need streams and plays to make revenue.

They can’t sign you without a single or if you can’t (or won’t) make traditional records.

Harry Mack is creating his path by building out content and creating fans along the way.

Let me show you his path after he graduated college.

How Harry Mack Carves His Path

Struggling as a jazz drummer, he never stopped freestyling.  

It was a part of Harry Mack’s soul – something that kept calling him back.

He had a friend that asked him to do a favor.

His friend Jacob was trying to get some attention to a musical track he had created, and he had the idea for Harry to freestyle over it.

So Harry did a freestyle while riding in the car.

The next day, the video went viral and had over 100,000 views.

Harry felt something was there, and this was the push he needed to share his craft with the public.

And So It Began

In 2017, he began recording the freestyles he did for people on the streets and putting them on his new YouTube channel.  

The first video on his own channel that went viral was called Venice Beach Freestyle.

He soon created a series called Guerilla Bars.

And Harry Mack kept innovating and putting his content out to the public.

And not simple raps.

Like, mind-blowing, mouth-dropping freestyle raps.

He’s Winning Fans Over One By One

But…

It’s not just one by one.

Instead, it’s one by one = Infinity.

Every time he freestyles, he gains new fans watching, yes.

But I see everyone recording his freestyles.

What do you think folks do with those video clips?

That’s right. 

They post them on their social media channels to their friends.

They say, “Yo! Check out this freestyle we just saw from this guy @harrymack!”

So a group of 5-12 folks, Harry does a freestyle for leads to hundreds or even thousands of new followers.

I found an interview Harry Mack did in 2020 

He had 500,000 YouTube subscribers at the time and was stoked about it.

Spectators (now fans) called him the ‘David Blaine’ of freestyling because it was like a street magic show.

Harry Mack’s fans also gave him the idea to start Omegle bars.

Harry was hesitant because the site could be a bit sketchy, but he tried it and was blown away.

He can record authentic reactions from people and then use those in his video content.

It’s brilliant.

In 2021, I found a Harry Mack interview with NPR.

At this time, he had over 1,000,000 YouTube subscribers.

He was doing a 10-hour freestyle rap session to celebrate this.

Notice that he’s constantly pushing creative boundaries and trying new things.

To my entrepreneurs reading this, sound familiar?

Remember us talking about the compound effect?

Harry Mack is putting the compound effect put into action!

Harry Mack Interview with Lewis Howes on The School of Greatness

This Harry Mack interview aired in 2022.  

Of course, he rapped for Lewis Howes.

I learned a bit more about his story.

He talks about channeling the inner child.

He compares ‘creating’ to a child that is finger painting.

Children don’t judge their art. They’re just having fun.

They ‘create.’

As we get older, we get more self-conscious.

So he encourages us to create just like children finger paint!

After college, he also worked at a call center for a bit, asking for donations to the music department at USC.

He says it was great for him.

Harry Mack learned to let rejection roll over him and not take it personally.

Second, he learned that you never know what folks can do if you don’t ask.

Tasked with asking folks for $200, he thought he would never collect that from anyone.

But every now and then, folks were willing to hop on board and donate.

Third, he learned how to talk with people.

An introvert at heart, this skill helped him be able to go out in public and ask folks if he could freestyle rap for them.

Harry Mack and Fear of Rejection

Harry Mack says the biggest fear is for folks to step up and Be That Artist.

To build in public.

Making yourself vulnerable.

Exposing yourself to feedback and criticism.

But it has to be done.

Harry Mack warns that as a creative, you have good taste.

This good taste inspires you to want to create yourself.

Because of your good taste, you can recognize you don’t have the same skill level.

But the only way for you to close the gap is to create.

Put out content and get honest feedback to get better.

Be in love with the process of creating.

And not just the end result.

So where are we now?

Harry Mack Today

As of this article, Harry Mack has more than 2M YouTube subscribers.

He also has 5M+ TikTok followers, 700k+ on Instagram, and so on.

He’s launched a Patreon where fans can further support him.

And now, he’s got some tour dates where you can watch him live in addition to his online creations.

As an entrepreneur, I’m excited to see where this creator heads next.

I see live shows where fans get an original performance.

Nobody knows what will be created, but they know it will be incredible.

Where the audience can interact and throw out words.

Then, every fan gets a copy of the show to watch and share with others (which would fuel even further growth!)

Harry Mack, I appreciate what you’re doing.

You’re not just thinking outside the box; you’re destroying that box!

Keep shining the light.

And now, for some Harry Mack FAQ…

How Did Harry Mack Get Famous?


As a freestyle rapper, his first viral video was one that he created called  Venice Beach Freestyle.

This allowed him opportunities to cross paths with Kendrick Lamar, Ellen DeGeneres, and Red Bull.
It also led to a TV commercial with Mitsubishi with a “Freestyle Test Drive.”

Now he has more than 7 million followers across his social channels.

Harry Mack and Kendrick Lamar?


Harry Mack often talks about his rap idols like Eminem, Nas, and Kendrick Lamar, among others. In 2017, Harry Mack was able to freestyle for Kendrick.

Harry started nervous (understandable!), but you could see him settle in and gain confidence.

He earns the respect of Kendrick Lamar, with Kendrick telling Harry that it inspires him to keep pushing himself and get back in the lab with his pen.

How Does Harry Mack Make Money?


With his social media following alone, he can make a full-time income.

You can have a look on Social Blade to make your judgments on the amount of money.

He’s a partner in the YouTube ad program and makes at least six figures in revenue from that one income stream.

He has a Patreon account where he shares exclusive items with fans. You can publicly see the number of patrons he has.

He also sells merch and is building out tours. I’m happy to see a freestyle rapper crack the code and create a business out of his passion.

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Brooks Conkle

Brooks is an Entrepreneur, Sponge, Father, Husband, & Follower of the Golden Rule. He has over 15 years of experience as an entrepreneur after graduating with a BSBA in Finance from Auburn University. He’s addicted to growing new business ideas and any food that includes chocolate and peanut butter. Brooks is a firm believer in creating multiple streams of income and creates content here on BrooksConkle.com to help other hustlers in the areas of marketing, online business, personal finance, and real estate.