Jermelle F. Pitts of Greatwood Underwear: “Every leader and entrepreneur should know this already but just in case you forget”

The most important thing that I’ve learned that I wish I would have known prior to starting is the importance of automation. Set as much as possible up for automated services. Also, be okay with delegating tasks. This will allow you to free up your time. As part of our series called “5 Things I Wish […]

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The most important thing that I’ve learned that I wish I would have known prior to starting is the importance of automation. Set as much as possible up for automated services. Also, be okay with delegating tasks. This will allow you to free up your time.


As part of our series called “5 Things I Wish Someone Told Me Before I Began Leading My Company” I had the pleasure of interviewing Jermelle F. Pitts.

Greatwood Underwear is an American brand made in Los Angeles, California founded by Jermelle F. Pitts, C.E.O & Brand Director. Greatwood Underwear is comfortable, modern, breathable and stylish. As the Brand Director Jermelle’s focal point is to provide quality underwear to men who aspire to be great throughout their hectic day. “I’m proud to share this collection with men across the world. It’s been a goal of mine to bring confident and driven men together. I am now able to do that with Greatwood Underwear.” Said Pitts in Contrast Magazine

The ancient symbol of wood has been found to represent physical and spiritual nourishment, transformation and liberation, union and fertility and often seen as masculine.

Throughout Jermelle’s career as a wardrobe stylist his work has been displayed on television networks such as N.B.C. Universal (E! & Bravo), Oxygen Network, FOX, VH1, MTV, B. E. T., TV One and WeTV.


What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

My “aha moment” was one day I was doing laundry and it was laundry day for underwear and gym shorts. I literally was folding underwear that seemed to be a never-ending pile. I was like wait; I should create my own underwear line. I know what fabrics and styles that I love and don’t like. I know my favorites cut; I know my price points when I’m shopping for underwear. Also, I’m a creative director. It will allow me to continue to put together photo shoots and work on marketing campaigns. Then boom Greatwood Underwear was created.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

For me I don’t have any investors at all. So financially it was really tough starting my brand because I was working on my own per diem for the day-to-day finances. I wasn’t able to blow through 250k dollars that someone had given me for inventory, marketing, payroll, legal fees and other business expenses so it was taking more strategy and time to scale my business. I honestly never considered giving up. I’m not a quitter. I would just go back to my business plan and marketing plan and tweak things but giving up was never an option. I just knew how bad I wanted this brand to work. I knew what I had invested in it and I understood there was a need for what I was offering so I kept going. My goal is to employ a staff of 60 or more and I knew if I gave up on myself, I would be giving up on other people’s livelihood as well.

So, how are things going today? How did your grit and resilience lead to your eventual success?

Things are going really well today. Business is booming. I’ve created some really dope partnerships. I’ve just released another collection and it’s been one of my best-selling collections to date. I’m extremely motivated and blessed. I have an amazing team that’s working with me and every day we continue to collaborate and drive the brand that you all know as Greatwood Underwear. I believe not having investors really pushed me. I couldn’t fail. If I fail or give up I lose all of my own investments. I believe my drive and determination have led to my Online success. My website numbers have gradually increased each day to be transparent. I’m still impressed about the website traffic to Greatwoodunderwear.com.

What do you think makes your company stand out? Can you share a story?

The name is very tongue and cheek. People really gravitate toward the name because it’s such a bold statement. Another thing that makes Greatwood Underwear unique is it has me. Those other companies have a lot of things, but they don’t have me. However, one of the main things that makes Greatwood Underwear stand out is that we have our signature orange eco modal fabric as a contrast in each pair of our underwear. The eco modal fabric is breathable and anti-odor. We make our underwear with the balls in mind.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?

When you’re a startup business no mistake is funny. Mistakes mean you wasted money and or time somewhere. Let’s say this a funny mistake that’s not so funny is hiring family members to work for my company. We had a fun work environment but because people were kin to me, I don’t feel they took the position as seriously as they would have if they worked for someone else. The lesson I learned from that mistake is don’t hire family members. It’s my business not the family business and I have to remind myself of that.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

That’s a hard question. I don’t allow too many people to give me advice. I think the worst advice I’ve been giving in business is that you need to be inclusive. I found that you will never in life appeal to everyone. There’s always going to be someone that doesn’t like what you’re doing. If you focus on trying to appeal to everyone, you’ll lose focus on providing a great product to those that’s already engaged with your brand.

You are a successful business leader. Which three-character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Listening to understand. When my team tells me, they don’t like something, or they don’t think an idea will work. I try to understand it from their perspective. Another characteristic that I have is I’m resourceful. If I don’t know something, I will find it. If I don’t understand something, I will research it. My third characteristic is delegation. I’m really good at handing off tasks. I’ve learned that in order to run a successful business you have to be able to assign tasks to people. However, I don’t ask people to do anything that I wouldn’t do myself.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

I don’t know. I don’t have any. I mind my business, let them figure out their own exhaustion and business.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

Focusing on the competition. Don’t come in the industry focused on who is doing what. Don’t come into the industry trying to take someone out. Don’t come into the industry pointing out someone else’s flaws. That is so weak! You’ll run your business into the ground trying to keep up with me. This is God’s plan, you can’t compete! What’s for me is for me. What’s for you is for you. What can be done to avoid those errors is simply focusing on the business that pays you.

In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?

I think being a jack of all trades within your company is really underestimated. My friends are like you’re always busy, but they don’t realize I’m the founder, the CEO, the accountant, the social media manager, the production manager, the attorney, the janitor, the customer service rep. I am really wearing every hat. I think every business owner will understand me.

Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Began Leading My Company”? Please share a story or an example for each.

That’s a very interesting question. I think one of the things that I wish I would have known or had a better understanding of is that your passion is a small percentage of being an entrepreneur. I’m a designer but I only spend 20% of my time actually designing. I spent the bulk of my time scaling the company, creating and implementing marketing plans, overseeing my staff just making sure the business aspect of things aligned.

The second thing I wish I would have known before becoming an entrepreneur is cash flow management. When I first started my company, I didn’t create a budget. I honestly just paid the price. If I needed this or that I just paid for it. I didn’t set aside a production budget and a marketing budget so by the time I had launched Greatwood I had already spent so much money.

The most important thing that I’ve learned that I wish I would have known prior to starting is the importance of automation. Set as much as possible up for automated services. Also, be okay with delegating tasks. This will allow you to free up your time.

The most important thing that I wish I would have been taught is to have fun. When you’re an entrepreneur and you’re leading a team there’s a lot of pressure to run the business, so you forget to have fun and enjoy the smaller successes.

Every leader and entrepreneur should know this already but just in case you forget. I want to tell you prior to starting your business have or create multiple streams of income.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

For the police to stop killing black people and arrest that thug that killed Breonna Taylor. Also, let’s stop homophobia and transphobia. 2021 be more cultured and open minded. I would also like to influence people to mind their own damn business.

How can our readers further follow you online?

The best way is to subscribe to www.greatwoodunderwear.com you’ll receive exclusive discounts and be the first to know when new items are dropping. You can also follow @greatwoodunderwear on Instagram. My personal IG is @jermelle and like my Facebook page Greatwoodunderwear.

This was very inspiring. Thank you so much for the time you spent with this!

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