Community//

Ashley Bolling: “It takes money to make money”

It takes money to make money. — One of my bigger business lessons has been to not be afraid to spend money. Most people starting their first start ups have never maneuvered with anything over a few thousand dollars before in their life. So naturally with starting a business, you nickel and dime everything just to get […]

The Thrive Global Community welcomes voices from many spheres. We publish pieces written by outside contributors with a wide range of opinions, which don’t necessarily reflect our own. Community stories are not commissioned by our editorial team, and though they are reviewed for adherence to our guidelines, they are submitted in their final form to our open platform. Learn more or join us as a community member!

It takes money to make money. — One of my bigger business lessons has been to not be afraid to spend money. Most people starting their first start ups have never maneuvered with anything over a few thousand dollars before in their life. So naturally with starting a business, you nickel and dime everything just to get it moving not even realizing that at some point, the quality of what you can produce in a lot of circumstances require a certain quantity of capital just to function at a healthy operational capacity. I say all the time that I definitely appreciated the learning curve of when I was running a business on nickels, especially because most times if you’ve never done something before, you don’t even know how to spend the money most effectively even if you did get it.


As a part of our series about women who are shaking things up in their industry, I had the pleasure of interviewing Ashley Bolling, President of Closet Freekz International.

Ashley Bolling is an emerging business curator with an eye for creative business concepts. She has become a successful entrepreneur with the launch of her sustainable fashion brand, Closet Freekz International in Orlando, Florida. This motivated young businesswomen is on the forefront of becoming a multi-faceted entrepreneur and investor with her ultimate focus on launching her business management firm, Adventureous Jill. Many of Ashley’s best attributes can be accredited to her years as a collegiate athlete at the University of Central Florida and years of service in the U.S. Army. While in the military she began pursing her entrepreneurial interest. She started “Closet Freekz” and steadily gained traction by combining innovative elements of fashion with cutting-edge style. Ashley’s determination helped her endure many early challenges as she continued to expand.

Ashley has been able to use her growing business influence to reach a broader audience, while using savvy business tactics to gain more notoriety.

The Closet Freekz International brand offers unique selections of vintage and repurposed fashion options for Men and Women. The future of the store includes an addition of 10–20 unique locations across the country. She wants her brand to represent the freedom to dress how you want, and be as different as you want. She believes, “depending on the day, either create your fashion or let your fashion create you. Either way, fully commit and fully submit.

​Ashley Bolling defines success as an ability to manifest ideas into reality. This savvy, independent entrepreneur has shown that she is capable of conquering any endeavor. While Closet Freekz International continues to blossom, she has several new ventures on the horizon. This fearless, businesswoman has successfully developed a solid foundation to build on for years to come. She is focused on creating a legacy and being a good role model to both young men and women.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I got in the business of resale apparel observing the need in the traditional fashion market space for a high-turnover fashion option that could allow customers access to large quantities of low-cost fashion options that could also be sustainable. Overall, just a DIFFERENT way to shop. For the last 25 years, I saw little advancement in how sellers (especially brick and mortar) enhanced customer’s shopping process and engagement. At the time I started, fast fashion brands dominated the millennial and gen-z attention span and shopping dollar. Meanwhile, textile pollution was holding strong as the world’s #2 largest global polluter. I needed a retail answer that could compete with the allure of popular fast fashion culture; including the ability to bring seasonal trend-relevant collections, stock a supply consistent with fast turnovers, brick and mortar access where big fast fashion stores are typically found, and all while, still achieving a competitive price point to win over the customer. The challenge of that amazing task, (especially during a changing fashion industry and shopping culture over the last 5 years) has advanced us in a unique space where we have become a front facing favorite as an alternative to traditional retail shopping.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

It’s our obsession with the growing uses for the technology industry as a whole and how we can use new concepts to enhance how a young person shops. Our proprietary ‘Silent Shopping’ was one of our first major tech integrations we adopted inside the mall. Having customers access stimulating audio and video channels of their choice via headphones increased the average shopping time of a customer by 60%. Shoppers could even venture around the mall area with to continue their experience shopping and return before leaving. Corporate partners of the mall reached out about how to adopt a further partnership with us based on the talk of the experience by customers. This concept was developed from the original playlist option we launched on eCommerce years ago that let customers shop the website via music. The increase of average time spent on pages was remarkable, and I knew we had to develop something like it for brick and mortar. That is just 1 of 7 concepts so far that makes the way Closet Freekz sells its product to the customer different. We like to encourage the customer to get back into physical shopping more by making it more than shopping but a Retail Attraction. Now that is how you get disruptive.

When it comes to What we sell, we have spent 3 years developing a proprietary sourcing method to gather unique selections of secondhand fashion from all around the world and bringing them in seasonal collections into a store near you. Unlike your traditional second hand retailors like Plato’s Closet or Goodwill, our inventory isn’t just a smorgasbord of discarded trends from your local area. Our fashion is hand selected for rarity, style, and uniqueness from fashion markets globally. Not to mention including products from past trends cross-generationally. How we source has allowed us to develop and bring some of the wildest most unique fashion collections each season to our shelves. Shopper’s love the variety of the selection and the exclusiveness of it being a one of a kind piece. Nothing feeds a millennials’ sense of individuality less than a rack of 30 of the same item. We found that people want the excursion of thrifting, without the work and aimlessness of it. But still the uniqueness and thrill of the find. So when it comes to our inventory and merchandising, That’s us! That is the fine and unique line of the Closet Freekz product experience.

We all need a little help along the journey. Who have been some of your mentors? Can you share a story about how they made an impact?

One of my biggest mentors thus far has been a business and spiritual mentor of mine named Preston Willingham. Preston’s success and expertise, which comes from a lifetime of success in patent and product development, has helped give me raw guidance and honest support throughout my years in business. When I met Preston, he was just at the tail end of finalizing a buyout for his company and the patent he’d created for the design of a global shoe company called Crocs. Since I’ve met Preston, he has only ever spoke to me about the importance of being innovative and about ways to disrupt your marketspace starting from the conception phase. As a serial patent expert, He’s always seen business as a creative space and encouraged me to always start from out of the box when strategizing, and not be afraid to put things in conception that seem different or new.

Preston’s business perspective continues to help me be impactful when growing and scaling my companies. I have grown to appreciate the freedom that Preston’s stratospheric approaches guides me in developing my business.

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

The Bigger the problem the bigger the opportunity.

Some of the most widely known entrepreneurs started off just doing something that they were interested in, but were able to pivot the concept to scale because they were able to tap into a larger need for what it was they were providing. When I started my company, originally it was because of my interest in fashion and the brilliance of using resources that already existed. But the ah ha moment that I could make a chain to compete nationally with retail leaders in my price point when I realized there was such a greater need for what my company was doing. Pollution is not just a niche problem. It is an ALL OF US problem. The pollution of textiles will have global effects if likeable, usable, and realistic sustainable alternatives are not developed to substitute them. Thus a global problem will always need a global size network of solutions. Which will leave you a wide-open market space for opportunity.

It takes money to make money.

One of my bigger business lessons has been to not be afraid to spend money. Most people starting their first start ups have never maneuvered with anything over a few thousand dollars before in their life. So naturally with starting a business, you nickel and dime everything just to get it moving not even realizing that at some point, the quality of what you can produce in a lot of circumstances require a certain quantity of capital just to function at a healthy operational capacity. I say all the time that I definitely appreciated the learning curve of when I was running a business on nickels, especially because most times if you’ve never done something before, you don’t even know how to spend the money most effectively even if you did get it. But hearing the advice not to be afraid to spend money to produce the most adequate model for success was kind of like a weight off my shoulders and opened a new perspective about how I saw the function on money to a busines. Learning that concepts need money just to spend on making mistakes just to get to the best product was revelation. So when I talk to new entrepreneurs about setting sights for their businesses, the plan to spend money is always in the cards.

Problems are apart of the process.

Back when I was first really growing my business, I was about 23 and still really learning on the fly about cash flow and how to build and raise finances for our operations. We had gotten behind on our rent one month after having the lease a little over a year. There had been so much press and pressure around us opening in this particular location because I was not only the youngest, but the only African American, and the only African American women to get approved by the city to open a business in this very regulated retail area of Downtown Orlando. In fact, the building had denied my application twice originally, deeming our products and the company “too urban”. At the time it required me to reach out to my contacts all the way up to the Mayor in order to shake our approval to gain that level of visibility. So at the first sight of falling behind on our rent, I completely began to panic. At the time I wasn’t really saving much, I was putting everything right back into testing concepts within the company. A month went by, and 2 months went by and I couldn’t support our expenses or my own at the apartment I was living in a block or so away. I had begun looking for someone who could give us a loan, but the process was being drawn out. I stopped by to see one of my mentors one evening on the brink of just feeling unprepared for the opportunity I had fought to get. And I learned one of my biggest lessons that moment when he told problems are apart of the process. And as simple as it sounded, it was the realization that problems weren’t just a phenomenon limited to my experience. That everyone involved, including him, and all the agents working in my leasing offices were not foreign to the idea that I could be experiencing an unplanned problem and just need to simply communicate it to them. It lifted a weight off my shoulders and my life because it lifted the shame in messing up, coming up short, changing the plan, or making mistakes. From there, it empowered my ability to avoid rifts in business altogether moving forward, just by simply communicating when a problem has arisen and that a bit more grace might be needed while we find the solution.

We are sure you aren’t done. How are you going to shake things up next?

Well, one thing I love of about Closet Freekz is its endless canvas of integrations that challenge how we shop for and how we collect our fashion as consumers. More immediately, we’ll be live streaming the first virtual fashion show in Central Florida from our live shopping experience Labor Day Weekend. Customers who usually shop via the live shopping feature online, will be able to watch the show across the world as we premier our Fall line. Guest of the show will be experiencing all the sounds of the show via our silent shopping headphones which will allow them to watch the same show, but interchangeably with the music audio of their choice. Guests online will have the option to toggle between camera feeds with either sound track as well. After which, we’ll be doing a virtual press conference explaining the line, that both inhouse and online guests can tune into on a 3rd headphone channel. That’s just one example of how we love to embed tech to enhance how customers can experience a brand. In addition to our up and coming stores in Miami and Atlanta for 2020, we have a few ecommerce enhancements rolling out in 2021 that we hope will help launch sustainable fashion into the subscription market.

Do you have a book/podcast/talk that’s had a deep impact on your thinking? Can you share a story with us?

When it comes to the “staple” books of my library, of course reads like The Alchemist, The Magic Ladder to Success, The Power of your Subconscious Mind, and many others were pivotal in helping me though the PROCESS of grass roots entrepreneurship. But I think ironically, it’s been the most random of reads that stick with me in my craft on the day to day. For instance, there is a book entitled There Is a River, The Story of Edger Cayce. And it’s and irrelevant little book in the context of business or entrepreneurship. And quite frankly a dry and drawn out read. But it’s the true story of a man, one of the earliest most documented clairvoyants in America. He’s very average, uneducated, simple, and otherwise carrying no particular talents or skills at all. Yet he lives life in the discovery of a gift that in his sleep he can access all the knowledge of the universe, even though when awakes, he can’t remember or is even intelligent enough to understand the brilliant teachings he’d just given in his readings while being asleep. I liked the book because by the ending of both his life and the book, he’d been the vehicle of information for a lot of other brilliant minds in the medical field who went on to start research and develop cures that changed how we use treatment here today. But the take away from it for me is that at any time, at all times, even the most simple man (women), without needing to be the most educated, have the most talent, or be the most equipped in business.. You can always access the power of the all-knowing source inside you to guide you and help you though along the way. Whatever for you that may be. And I think it’s the overall trust in oneself that makes a disruptor a disruptor. Because even when you’re pursuing a path not yet uncovered or going up against changing the way something has always been… you can trust that there is indeed “a river, whose streams make glad where the most high dwells”. He entitled the book after Psalms 46, which after reading it, becomes one of the last most brilliant and inspiring things I realized he did.

You are a person of great influence. If you could inspire 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. 🙂

I’ve been intentional on the idea of strengthening a generation of women and minorities in business. I believe there is an uprising renegade wave of brilliant disruptive business concepts that would come from the watering and nurturing of traditionally dispositioned entrepreneurs. For instance, In February 2021, I’ll be publicly launching my business management and funding firm. Part of the ideal I developed the firm around, was my past success in taking first time entrepreneurs who were either athletes, army veterans, and convicted felons on as clients. What I’ve found from this, that for different reasons, each of these types of individuals tend to carry unique sets of mental discipline, resilience, and networking skills that breed valuable traits for successful entrepreneurship. The only problem is really their positioning to knowing where to get resources to operate their concept to scale. With the structure and resources my firm provides, these innovative creators can have the opportunity to access a vehicle for ideas they have had time to put thought into, without necessarily needing the skill set and training in that industry to see it develop and scale. I like the empowerment that gives non-traditional entrepreneurs in the market space.

I’d also like to see younger women become exposed to more glorified ideals of businesswomen as well. As pretentious as it sounds even to me, as if Women in business don’t have enough to do as it is to be successful. But adding and exposing a level of “rock stardom” and glamour to the ideal of what it is to be a women in business can influence the younger generation greatly into choosing that path over more saturated lanes like beauty, and entertainment. I think women can be much more instrumental and dynamic in the big business ecosystem if they could potentially be groomed up that way. If I could choose an impact to leave, it would be to influence future generations of young women into this life. To give more support, stability, and power for women in the business world altogether. A “Girls club” per say to balance out the “Boy’s Club”. If I have daughters one day… my hope is that that barrier of entry in business will be more than broken. In fact, quite the opposite. That “being in business” for young girls, would be right up there with wanting to be a Disney princess or a ballerina.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

We build our businesses as we build ourselves

This is one of the most relevant truths that I heard from one of my favorite shows, Billions on Showtime. I thought it was the most wise and true quote that any true entrepreneur could know. Many of the short falls I’ve experienced in my company so far, and even the most accomplished moments were direct correlations to my own life and how I was growing out as an owner and growing up as an individual. The tempo of how I’ve had to build my own character is intertwined with the times that my company really needed those qualities from me as a leader. And in times where I felt like I had failed or hit a bottom… the way I built my company back up for it’s return was the same tools that I built myself up to return. I really do feel that an entrepreneur’s business overtime becomes nothing but a reflection on a canvas of who that person is creatively, in talent, in morals, and in leadership. So absolutely I believe that we build our businesses as we build ourselves. And quite possible just having that reflection as a guide can mirror back to you strength, courage, and insight as you continue to build along the way.

How can our readers follow you online?

You can visit my personal website www.jillbillion.com which will direct you to my social media. Closet Freekz International can be found at www.shopclosetfreekz.com.

This was very inspiring. Thank you so much for joining us!

Share your comments below. Please read our commenting guidelines before posting. If you have a concern about a comment, report it here.

You might also like...

Community//

How Ashley Bolling of Closet Freekz Is Shaking up the Fashion Industry With One-of-a-Kind Clothes

by Candice Georgiadis
Community//

Tips From The Top: One On One With Ashley Morris

by Adam Mendler
Community//

How I Thrive: “No matter how busy I get, I ALWAYS start my day off with a run” With Ming Zhao & Ashley Mason

by Ming S. Zhao

Sign up for the Thrive Global newsletter

Will be used in accordance with our privacy policy.

Thrive Global
People look for retreats for themselves, in the country, by the coast, or in the hills . . . There is nowhere that a person can find a more peaceful and trouble-free retreat than in his own mind. . . . So constantly give yourself this retreat, and renew yourself.

- MARCUS AURELIUS

We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.