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'I'll Sleep When I'm Dead' and 4 Other T-Shirts Every Entrepreneur Needs to Wear

Are you displaying your entrepreneurial beliefs on your chest? Time to start.

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Today’s workplaces are increasingly casual. The days of suits and ties (and pencil skirts and heels for women) may not have ended completely, as there is always a time and place for such formal wear, but comfort and self-expression play an increasingly important role in today’s fast-paced, innovative business environment.

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Related: 5 Ways to Foster Team Culture on a Startup Budget

The t-shirt is fast becoming a means for entrepreneurs (male and female) to represent those values. First, this attire and its artwork sends a clear message to the rest of the team. Second, it's worth considering that if everyone in your office were to take things a step further and wear the same t-shirt as you, they'd contribute to a strong corporate culture and sense of unity.

You'd also be eliminating the need for everyone to put a lot of effort into dressing up every day.

Additionally, more and more people are seeing the business opportunity in t-shirts, and building companies based around them. You don’t need to look much further than Merch by Amazon to know that this is a growing trend. And, in this context, Make Merch is an easy way to make your custom t-shirts.

Here are a few of our favorite Merch by Amazon t-shirts designed for entrepreneurs.

The "I’ll Sleep When I’m Dead" workaholic t-shirt

Image credit: Entrepreneur Hustle Tees


The “I’ll Sleep When I’m Dead” t-shirt was created by Entrepreneur Hustle Tees. The company offers several other design offerings for entrepreneurs that are worth a look.

Related: Why One Man Came Out of Retirement to Start a Custom T-Shirt Franchise

This one is great because the catchphrase is straightforward, and one entrepreneurs can relate to. “I’ll Sleep When I’m Dead” pops in big bold blue and silver letters, accompanied by an illustration of a laptop with an airplane in front of it. The modern entrepreneur is used to the idea of working long hours to achieve his or her dreams, and is willing to make the sacrifices necessary to get ahead. There is no t-shirt that embodies this philosophy as much as this one.

The shirt is available in: asphalt, black, slate, navy and heather blue, to suit whatever color preferences you or your office might have.

The "American Entrepreneur" make-that-money side-hustle t-shirt

Image credit: American Entrepreneur


For those who love a bit of early 2000s grunge in their designs, there’s the “American Entrepreneur” t-shirt by American Entrepreneur, featuring serif lettering and a worn-out, hard rock American flag in the background.

With this shirt, you can wear your country’s “colors” while proudly declaring the role you play in the world. It’s perfect for those concerned with promoting a return to American industry and people who are proud to be building their business in the United States. It’s the perfect excuse to rock out in the office.

The American Entrepreneur t-shirt comes in asphalt, black, brown, royal blue and navy.

The "Professional Button Smasher" t-shirt

Image credit: Conference Shirts


The “Professional Button Smasher” t-shirt, produced by Conference Shirts, could apply equally to a frustrated entrepreneur, designer, gamer or anyone who works primarily at a computer. For those with a bit of personality or sense of humor, this is the perfect shirt to make your coworkers laugh.

The are many benefits to incorporating humor in the work environment, including helping people enjoy their work more, contributing to a sense of well-being and motivating your team when things are difficult. Showing up to work with this shirt will put a smile on the face of your team members.

You can get the Button Smasher shirt in black, dark heather, heather blue, navy and white. The company has a few other designs for entrepreneurs looking to feed their inner geek.

The "Follow Your Dreams" t-shirt

Image credit: Follow Your Dreams Motivation and Persevere Tee


Most, if not all, entrepreneurs can relate to this sentiment: “Follow your dreams or you’ll spend the rest of your life working for someone who did.” All entrepreneurs know that following your dreams is not always easy, but the journey is worthwhile and fulfilling. Making your dreams a reality is one of the best reasons to be a business owner.

This is motivating, and reminds you and your team  why you do what you do, especially in those inevitable moments when the going gets tough. There are ups and downs in every entrepreneur’s journey, but the ability to create something great is what motivates many and to continue on that path.

The  t-shirt is available in black, red, heather gray, dark heather and heather blue. The seller is Follow Your Dreams Motivation and Persevere tee.

The "Authentic Entrepreneur" t-shirt

Image credit: ODS Entrepreneur Shirts


A simple but compelling design, this shirt features banner -- or product label-style text --that reads, “Authentic Entrepreneur – Hard Work – Dream, Believe, Achieve.”

Dream, believe and achieve is a simple motto that many business owners can easily latch on to as an effective reminder. It reminds you that if you just put in the work, anything is possible. It also causes you to focus on the core elements of building a business -- your vision, your belief in yourself and your team and your ability to achieve if you persevere through challenges and difficulties.

Seller ODS Entrepreneur Shirts has many, many other compelling designs for sale -- some meant for entrepreneurs, others for other interests -- so don’t be surprised if you come across something else that suits you as you browse its product offerings.

You can order this shirt in black, kelly green, olive, navy and purple.

Final thoughts

Even with workplaces becoming more casual, it’s still possible to feel like a “superhero” when you put on a stylish t-shirt with your favorite saying on it. You couldn’t ask for a more present reminder to live out your favorite mantra every single day as you build and develop your business.

Whether you’re looking to create a fun work environment, develop team unity or express your personal style, entrepreneur t-shirts present a great way to lighten up the office, enhance your corporate culture and build camaraderie amongst your team members.

Related: Want to Preserve Your Company's Culture As You Grow? Here Are 4 Ways.

For those in the t-shirt business, it’s good to be aware that there is a huge potential opportunity to tap into with a Merch by Amazon business model. If you aren’t already, appealing to entrepreneurs with your t-shirt designs could open a new market. Getting set up on Merch by Amazon is easy enough, and if you have unique designs people love, it’s possible to earn five figures per month selling shirts.

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