Four Real Life and Inspiring Examples Of True Hustle & Grind

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What is hustle and what is grind?

Not this website specifically (though, if you are not sure what we are about, feel free to take a look around), but what do the words mean? And how does one hustle and grind?

Rather than define the words themselves – that’s what the dictionary is for – let’s look at people who exemplify the words. You can talk about hustling and grinding all you want, but there is no better definition than living and leading by example and personifying the idea behind the words.

The Definition Of Hustle

Hoodie Allen


In the fall of 2014, rapper Hoodie Allen (Steve Markowitz) released his debut album People Keep Talking. Though “debut” is a bit of a misnomer as Allen had released 5 mixtapes and several EPs prior to the release of his first studio album. His first mixtape, Bagels and Beats, was released in 2009 when Allen was a student at the University of Pennsylvania.

He continued to release various mixtapes and EPs throughout University and even as he began a job at Google as an account executive. Four years of school, and a job at Google right out of the gate – something most people would be thrilled with. In fact, something a lot of people would use as reasoning for letting go of their dreams or passions and it would be hard to blame them for doing so.

But Allen could not turn off the dream that easily so while his days were spent at Google, his nights were about writing, recording, marketing, meeting with record labels, selling merchandise, booking shows and performing. Sounds exhausting – it probably was – but that is hustle to a T. The candle has two ends and sometime you need to burn them both to get where you want to go.

There’s that saying “Work smarter, not harder” and while it’s a great sentiment, sometimes you need to do both. Work hard in school, work hard at Google, and work harder on making his rap dreams come true. That same marketing savvy he learned about in school and propelled himself to a job with Google is the same savvy he used to gain a following online.

All of that culminates in a chart-topping self-released album. Even though those record label meetings proved for naught, Hoodie had enough of a following that he could do it all on his own. The work comes, the time flies by, then all of a sudden you are watching the Grammys at home and you hear your own song playing as a presenter walks out.

We have all been there before…

Sara Blakely

Well, maybe we haven’t all been there before. In fact, some have been beyond that level of success – such as having your product featured on Oprah. Not just featured, but being worn by Oprah herself.

It happened to Sarah Blakely the creator and President of Spanx, at least. Blakely wanted to become a lawyer but failed her LSAT, she then worked at Disney World, tried being a stand-up comedian, and sold fax machines door to door (the 90’s were a different time). Working her way up at that company, she came up with the idea for Spanx – a female undergarment that firmed the body’s appearance and did not show lines like traditional pantyhose.

While still working at her job, Blakely researched the idea for Spanx. When she finally had her design nailed down she needed a patent. Not wanting to pay the legal fees to have her patent written by another party (applying for the patent is costly enough) she wrote the patent herself. All of that was just to get the product made. On top of that there was marketing, manufacturing, distribution and physically getting her products in the stores. To overcome the established brands.

A good idea is merely the beginning, yet they can lead to product appearances on Oprah, a billion dollar valuation. These products and people seem to pop up overnight only because we do not see the sleepless nights and sheer force of will behind it all.

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The Definition Of The Grind

Ramit Sethi

Sethi has developed his own brand and company with his program I Will Teach you to be Rich. This is not an advertisement. His blog and newsletters are read by thousands of people weekly. Hundreds of thousands, to be exact. In addition, his book of the same name was a New York Times bestseller in 2009.

With an established brand and a popular newsletter one can easily forget that it was not always this way for Sethi. In fact, Sethi wrote his blog for over three years before he ever made a cent from it. Even then the profit wasn’t from the blog itself, but an additional eBook he sold through his site. Most people would give up after a couple months or maybe a year. It takes a certain type to continue on without seeing any financial fruits being born from their labors. That is taking the first rule of any side hustle to heart – you need to love what you do.

Writing the blog, and selling his strategies as an eBook, Sethi ended up making more money off his “I Will Teach You to be Rich” brand than he was at his job. What’s that? Yes, Sethi had a full-time job at a Silicon Valley start-up while developing his own personal brand.

Sethi loved writing about finance and the strategies therein. Although the blog was about teaching others how to make money, it was not profitable for Sethi, but it was about building an audience. Through this Sethi was able to gain trust from his audience and build rapport. Again, all this being done while Sethi was in school and/or working full time at a start-up. “Start-up” companies traditionally do not come with a lax work schedule.

As hard as he worked to become established – Sethi attributes some of his success to simply sticking around. The idea being that those who fall by the wayside, who move on, settle, or simply give up can miss out on opportunities. By grinding his way through work, his blog, and his content, Sethi’s audience grew organically and he was so well practiced at what he was doing he was ready when his star took off.

You cannot say “the rest took care of itself” necessarily but putting the work in can pay off with huge dividends even if they are not seen right away.

Tim Ferriss

Tim Ferriss’ three “4-Hour” books have all become New York Time bestsellers. Having become downtrodden with his own 70+ hour work week schedule, Ferriss developed his own process for cutting back on his schedule while maintaining status quo business operations. Inspired to help others with the same problem, Ferriss wrote a 300+ page book deriding the typical work week process and suggesting his alternative.

Having a great idea and then writing the book is one thing. It seems like a big step and it is, but in terms of getting a book to, you know, actually be sold in bookstores – the effort of writing the book itself is only a fraction of the workload. Once Ferriss has completed his book he was turned down by a publisher. Then another, then another. 25 publishers up and 25 publishers down – all said no. Tim Ferriss was on his way to a perfect game.

He could have given up. He could have tried to self-publish or create made it into an eBook online to distribute to a fraction of the audience. To get some eyes or any eyes on his book. Instead he went right to the next publisher on the list and, finally, sold his book.

There are thousands of other stories just like these. Those people we may perceive to be better than us or more successful. It can be difficult to imagine them having been in your shoes. But they have been in your shoes – they were not handed anything. Sure luck comes into play here and there (maybe Ferriss would have quit after 26 rejections) but you need to be good to be lucky and you need to be prepared when luck and hard work and persistence all come together.

hard work

While Ferriss is mostly known as a writer, he did once refer to publishing a book as “The most unrewarding, unsexy approach to masochism.” Yet he’s built his brand from publishing and his blog. The painful path to a lifetime of success. Now he offers business retreats to Richard Branson’s private island. This would not be the case if he stopped at 10 rejections, or 15, or 20.

Magic: Combining the Two

Ultimately, the above mentioned men and woman combined both hustle and grind to get to where they are. Writing, becoming a best-selling author, a fashion icon, releasing a wide-selling self-released debut album – all these started as side hustles and passion projects. They may be referred to as a grind but I doubt Sethi or Blakely or Ferris or Allen would ever describe them as such in the moment. They had that fire to do the work on top of their other work without expecting or experiencing an immediate reward.

An “overnight success” worked many sleepless nights unseen and unheard to referred to as such.

It takes the right person to be in the right place and right time. It does not happen by accident. The lucky ones, the gifted ones, the natural talents, the ones that make it all look so easy to the outside world, they are the hustlers and the grinders.

Call it what you want to call it, make your excuses if you have to – at the end of the day every success story has one thing in common – hard work. Hustle and Grind.

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