How This Entrepreneur Hit $1M in Sales in 3 Years Selling T-Shirts With a Full-Time Job

Do you ever look at your to-do list and think, “I’mma go ‘head and let God handle that”?

How many times do you talk to someone who is draining your energy and say, “Nah, I’m good”? When Ari Simpson finds herself in that situation, she can just look down and read one of her t-shirts. Ari and her husband founded Tees of Life in 2020. They got such an overwhelming response that they just kept building. Less than three years later, the brand has hit a million dollars in sales.  

Ari can’t help but stay true to herself — after all, her own words are on her product! And that authenticity is applied to everything she does in her business. Simpson spoke to BLACK ENTERPRISE about how she uses social media to create a community of customers, her goals for being the largest employer in her county, and why entrepreneurs should just get started.

How did you grow a seven-figure business while working a full-time job?

Ari: On evenings and weekends I totally focused on growing my business. I missed out on a lot of events with my family and my friends. I just got laser focused on growing my business. Also, whenever there was a break in my 9-5, I did something to grow my business. I used PTO days and lunch breaks to work on the business. Whatever it took, I did that. Also, while I was still working my 9-5, I was still developing a team. We hired a VA, we had someone to help us with social [media], and we hired people to help us with fulfillment. I am now full-time in the business, but I waited until it hit the million-dollar mark to leave.

Tell me more about Tees of Life.

Ari: Tees of life is a statement t-shirt company. We create t-shirts with sassy messages of self love that help build confidence and give people, mostly women, what they need to just live life and be full of themselves for a little bit. My husband and I started the brand back in May of 2020, and we had no idea what we were doing. We just knew we wanted to make some t-shirts. And then we got such an overwhelming response, just from our local community, that we just decided to just keep building on it.

The timing really just came together. [Tees of Life] was an idea that I procrastinated on for about three years. Finally, one day, my husband told me, “You’re either gonna do it, or you’re not.”

When was the first time that you had this idea?

Ari: I’ve always been somewhat of a creative, so I dabbled with creating flyers and invitations for other businesses, and I quickly realized this is not really what I wanted to do. I was longing for an opportunity to kind of say some of the things I wanted to say, versus having to say what other people wanted me to say.

I was praying to God: “Okay, what is it you want me to do? What am I supposed to be doing?” One of the things that a lot of my friends will say about me is that I’m gonna motivate. And the answer to that prayer was, “I want you to keep doing what you’re doing, but in the form of t-shirts.” I put that gift that God gave me onto t-shirts because I love statement t-shirts.

I want people to be unafraid to just show up as themselves, right? And be okay with being confident. Women in particular pour so much into other people. Our t-shirts allow [women] to say, “I’m the one who’s all that. I love me. Not only do I love other people, and I take care of other people, but I feel great about me, too.” And that’s the message we really want to share. We sell t-shirts, but we also sell confidence and boldness. The message is, “Go out there, be you, be you boldly, show up, love yourself, regardless of who you are or where you are in your life.”

How do you define success for yourself? How do you know when you’ve hit that metric?

Ari: When I see other people wearing our shirts, it almost stops right there for me. Somebody somewhere thought enough of [Tees of Life] to be willing to pull out their credit card and make that purchase. Just seeing other people’s messages is really like a signal of success for me. But another thing that I pay attention to is our return customer rate. Sometimes, people impulse buy things they see on Facebook or TikTok. If they come back and buy again, then we know that the messages that we’re creating are impactful. We’ve been so blessed over the course of the last few years to have a really strong return customer rate. Most of the time when people shop with us, they come back and they shop again.

What were some of the strategies that you’ve used to bump up that return customer rate?

Ari: I show up on social media. Some of our customers that bought with us back in May of 2020 are still our customers because not only did they follow us, but we follow them. We interact with them. We know when it’s their kids’ birthdays. We comment on those things. People really start to feel attached to the brand. the messaging, and to me. Even now, we have a customer service team, but people will send us an email saying, “Hey, Ari.” Yes, we have a product to sell, but we are real people, and we believe in our messages. I think that really helped people really grow attached to us.

Have you ever felt the authenticity of your business was challenged as your business expanded?

Ari: Not yet. I do think that that could be an issue, and we’re ready to meet it head-on. We will always be authentic to who we are. The messages that we create are a part of who we really are as people as messages that we believe in. One of my goals outside of monetary goals, and boosting people’s confidence is to be one of the largest employers in our county. Even when we hire, we tell them, “you are now becoming a part of our family.” It’s a culture that we won’t waver on. We know that we want to boost confidence and boldness and authenticity. So how dare we ever get to a point where we get away from that?

You just hit a million dollars in sales. What are your goals for 2023?

Ari: Beef up our team! We’ll hire more folks that take care of the packing, the orders, and all of that. But we’ll also start to build out more teams around customer support. And just looking at the organization from a financial standpoint. This is where we are now, and this is where we plan to go. What holes do we need to fill in? What gaps are open now for a company that’s growing super fast? We’re open to bringing in more people that can come to consult with us.

Is there one thing that might have stopped you from getting where you are today? How did you either avoid it or overcome it?

Ari: T-shirts have been around forever, right? They’re a staple. When I first had the idea [for Tees of Life], people said things to me like, “Oh, everybody’s making t-shirts. There’s no money in t-shirts. What’s going to be different about you?” People watered down the whole idea. If I had let that stop me, I wouldn’t be celebrating hitting a million dollars in revenue this year.

Another thing that probably could have could have stopped me was just those feelings of overwhelm. Having to be a wife, a mom, and working nine to five gets tough sometimes. But I made a decision that this is what I’m supposed to do. It’s my gift to pour into other people. I have to do this. I have to figure it out.

What’s one thing you wish you knew sooner about growing a business of this size?

Ari: I wish I had started sooner! I wish I didn’t wait three years, and then I wish that I knew this level of success was possible for me. I knew I could be successful. But I didn’t dream this big, right? And it’s almost like, I had to get here to dream even bigger.

What is one thing that an aspiring entrepreneur could do in the next 24 hours to put them on the track to success?

Ari: Start! Yeah, just start. It’s simple, right? But you can never perfect the play you never ran. So you got to get started. We’re not perfect, but we get better the next day because of what we did the day before. You’re always going to be learning. Give yourself some grace and just get started.

Who are those people that you can turn to if you have made a mistake, or you need advice?

Ari: So I joined a t-shirt mastermind early on. I call them my t-shirt sisters. In that community, we learn some of the foundations of a successful t-shirt brand. We’re at different levels in business. Some have products in Walmart and Target. Some of them are about to move onto the next thing. But we still turn to each other for ideas, questions, you name it. And then as our business started to grow, I knew that I needed more business expertise. That came through in the form of masterminds, where I’m able to just consult with other business owners, accountants, and marketers. Those are the communities I lean into whenever I need help with anything.

How did you find the t-shirt mastermind?

Ari: I found it by just studying other t-shirt brands. When I saw brands that were killing it,  I reached out: “I love your brand. I love your shirts. Do you consult with others who are interested in starting a brand?” One particular brand owner reached out and said, “Hey, here’s my mentor. He’s awesome.” That was how I joined my first mastermind. In this group, there is no competition. A lot of people find that hard to believe, but I think that just speaks to the leader of that group. We collaborate and want everybody to win because we knew we could learn something from everybody.

How did you develop the mindset that “everyone can get a piece of the pie”?

Ari: I’ve always wanted to see other people win. I’ve always wanted to see other people feeling good and having a good time. I’m always the life of the party! It’s just a part of who I am. It was just all a matter of me finding the right communities that had that same spirit. And now I’ve learned that it’s only lonely at the bottom. Most of the time, people who are really successful or doing good for themselves don’t mind sharing.

Are there any things that you want to share with aspiring entrepreneurs?

Ari: I’m from a really small town — we have like one high school. Two grocery stores. It doesn’t matter where you’re from, as long as you can dream. And most of the time, you’re probably dreaming too small. As long as you can dream, and you’re not afraid to roll your sleeves and do the work, you can literally be and do anything in this world. I know that it sounds kind of like things we tell kids, but it applies to adults too. We can dream. Just last night, we shared with my 14-year-old son that we were about to be a million-dollar brand. And just to see his eyes light up is something that I really can’t even explain, right? So entrepreneurs: always remember your why. Why are you doing this? For me, I knew that the work that we’ve been doing tirelessly could be something to show our kids. Last night was the beginning of that. Remember your why. It doesn’t matter where you’re from, you can absolutely attain anything.

Do you mentor others looking to get started with their own t-shirt business?

Ari: I do and I have a free resource that will help both new and aspiring t-shirt brand owners get started. This resource includes information about some of my favorite vendors in the t-shirt space. They can get it here.

Where to Find Tees of Life:

  • Website:
  • Instagram: @teesoflife_official
  • Facebook: Tees of Life Official

About the author

Ashley N. Kirkwood is an attorney, speaker, and owner of a seven-figure consulting business. She holds a Juris Doctor from Northwestern Law and an International Business Degree from the University of Illinois. She has worked with large corporations such as Phillip Morris USA (Altria), Enterprise Rent-A-Car, Boeing, Microsoft, Blue Cross & Blue Shield, and others. 

Ashley has been published and featured in Crain’s Chicago Business, Black Enterprise, Forbes, Time, NBC Chicago, Fox32, Amy Porterfield’s Online Business Made Easy, Entrepreneur, WPRI 12 New, HF Chronicle, the American Bar Association, and others.