Entrepreneur Interviews

Interview with Greatwood Underwear Founder Jermelle Pitts

Life's hardest lessons and experiences fuel some of the most talented entrepreneurs. That's readily apparent in the story of Greatwood Underwear, founded by proudly black and gay entrepreneur Jermelle F. Pitts.

Jermelle Pitts is a fashion entrepreneur who has gained strength through adversity, whether that's the taunting he endured when he was younger or the hard business lessons he's learned while rolling out his underwear brand.

We love tenacious entrepreneurs, so we decided to learn more about Jermelle's business. Luckily, he was kind nice enough to join us for one of our entrepreneur interviews.

Thanks for joining me to tell us about your fast-growing business, Jermelle. Let's start with the basics. What's the offering and who do you sell to?

I am the CEO and Brand Director for Greatwood Underwear. We are exclusively sold online at www.greatwoodunderwear.com. You can also shop directly from our Instagram page @greatwoodunderwear.

We offer an assortment of underwear from briefs, boxers briefs, jockstraps for men. However, I would say thanks to my bestie Brooke Valentine; women are also becoming obsessed with our underwear and wearing them as biker shorts and lounge wear.

We also have some real dope merch like hoodies, joggers, and our signature tees.

That's interesting and awesome. How on earth did you get into that niche of starting an underwear line?

I was a fashion stylist and Creative Director for over a decade. I was working on a few television projects that were cancelled simultaneously.

At that time, I was just like cool, that's life, keep it moving. I was also working for my best friend as her creative director. She was gearing up to release her EP titled Sip, and all the songs are just so dope.

I was going to go on tour with her. I was super excited of the thought of my friend and I just on the road city to city on some Rockstar vibes.

Then boom she says "Jermelle Fucking Pitts, I'm pregnant." So, needless to say, we had to table the idea of going on tour.

So, I had to go back to my drawing board and see what I wanted next for my career.

I knew that I was ready to transition my career. I was at Brooke's house and I was like boom I have this idea. I want to create an underwear brand.

I've been wearing underwear every day since I can remember. I love buying underwear and just being at home dancing around in my underwear.

She was like "J, this is amazing. What do you need from me to get started?" I quickly told her "I need the money that I would have made being on tour with you." She was like "Okay, Say less."

She cashed me out, and I started Greatwood Underwear and the rest is history.

Now she'll tell the story that she got fat, I didn't want to style her anymore, so I retired and started the brand.

Wow, sounds like you two have a great relationship. It always amazes me how people get started in their various businesses. Switching gears a bit, I know you take great pride in being a gay black man. How has your identity shaped your entrepreneurial journey so far?

When you decide to enter entrepreneurship, you have to have a thick skin. There's a lot of rejection and wondering if what you are creating is good enough.

When you start a business, you are unsure if people are going to support you or just be like "this is weird, I want no parts."

I feel being a black gay man really helped me deal with the struggles and doubts of becoming an entrepreneur because I had already developed a thick skin. I learned as a black gay man everyone isn't going to support you.

That's the same in business not everyone will support you, but you have to find the people that will and offer them your best.

I have been taunted, bullied and rejected because of my sexuality and I have still had amazing highs in my life. At an early age there was a fight instilled in me and I learned that I could accomplish and be whatever I wanted to be in life.

I think some young black and gay entrepreneurs will find inspiration in what you've just said, but I want to get back to the underwear business. It seems like an incredibly crowded space. If you look for underwear online, there are just a zillion choices. So what's the market like? And how are you getting traction and rising above all the noise?

The underwear business is an interesting market.

I don't really pay attention to how saturated the market is. When you're an entrepreneur you honestly can't get caught up with who is doing what, you just have to create your vision and make it work for yourself.

There were a million singers before Beyoncé and there will be a million after her. What if she never started or focused on what the other girls were doing? She wouldn't be the most Grammy awarded person in history. All I am saying is if you focus on your craft and offering a quality body of work, then the success will eventually find you.

With Greatwood Underwear, I focus on the quality of the product and making comfortable underwear for men.

In every pair of underwear, there's a signature orange modal fabric. The contrast modal fabric is anti-odor and super breathable. Our customers really enjoy that feature.

I am just really focused. It's never been my reputation to deal with "noise." I think Nicki Minaj said it best "All that Ra ra never was the Icon issue."

Comfort and quality sound like two great things to offer in the underwear space. I like the strategy you've taken. I just have a couple more questions for you. The first one is having you made any mistakes along the way in your venture that you've learned from?

I've definitely made some mistakes in business.

I think that my biggest mistake in business has been relying on other people. I had the expectation that everybody on my team was as passionate as I am about the brand, and that just wasn't the case.

It was interesting because when I cut ties with certain people the brand started to move in a better direction. I also made rookie mistakes like not sampling certain items, and then there were things in production that were not right.

Also, becoming anxious to release items and then, at the last minute, scrapping the entire plan -- boy, were those some expensive mistakes.

Also, budgeting. I made mistakes with my budget. I didn't properly budget, and I was just spending money. My first two collections sold out, and I didn't really see the profit because I was so far in the red.

My second collection, I allowed my photographer to select the models and I hated a few of them, but they did the job and I still had to pay although those images will never be used.

Those are some tough lessons that only the real world of entrepreneurship can teach you, but the good news is that you made it past that and are still going. That's great.

My final question is simply what advice you might give to other black or gay entrepreneurs who are navigating the world of entrepreneurship? If you were mentoring them, what would be your top few bits of advice?

My advice to any entrepreneur is to keep pushing. Don't give up. We are all just one push away from our life changing forever for the better.

The greatest advice that I would have is protecting your business. Make sure that you've handled your corporation deadlines, taxes and trademarks.

More importantly, just follow your dreams and keep challenging yourself. Keep motivating yourself. It doesn't matter if you get one sell or one million. Do your happy dance and jig.

With that positive attitude, you are going to go far, I'm sure, Jermelle. You're building a great company and a great brand. Starting an underwear business might not be for everyone, but every entrepreneur can learn a ton from what you've shared with us. We wish you all the best as you continue to grow Greatwood Underwear!

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