Jaclyn Milford founded Women of Wallstreet out of a desire to forage a career path that reflected her true sense of self and the passion she has for honest connection. Ambitious and charismatic, her presence into any space can be felt. For some, this is attractive. For others, it is immediately rendered as a threat.
Jaclyn’s experience as a female entrepreneur is nothing new. Women have been fighting for respect in the workplace for decades, often hitting a brick wall when confronted with biases and stereotypes that attempt to pit them against men, or worse, one another. We have seen the rise and fall of the “girl boss” era where women felt “empowered” to throw on the pantsuit, walk into the boardroom, and claim their space in corporate America. However, Jaclyn realizes the fault in the movement through her own experiences. While many institutions acknowledge the value of women on boards, in executive positions, and as entrepreneurs, why aren’t more women stepping up for other women? And what are we really doing to ignite change in these spaces?
Knocking Down Doors
“I’ve always rebelled against these sorts of social norms that put us into boxes that tell us who and what we are supposed to be. At a young age I didn’t know why I did it, it was just my natural response in situations. As an adult I do it because I want to be in control of my own happiness and self worth.”
Jaclyn has always had a way of shocking people. She once decided to chop off all her hair and, in another stunt, showed up to school in clothes she made using her grandmother’s sewing machine from the industrial revolution. When she began singing in bands, she was seduced by the feeling of performing on stage and decided she would pursue a career in music. Not one to overthink the unknown, she left home at 18 for Gainesville with her band. She funded the endeavor by selling her car and cashing in her bank bonds to chase a dream. What may seem irrational for most was a no brainer for Jaclyn. She knew what she wanted and had the courage to go after it.
“I had big dreams, little money and only a few years of work experience under my belt, which made job options scarce. I ate bread rolls as dinner meals most days but I didn’t care. Looking back, I’m so glad I did that because even though it was short lived, I learned a lot about myself during that period.”
The Path Towards Self Determination
“I had already gotten the beauty job but that wasn’t enough, so I cocktailed in the evenings at this dark horrible place until I made enough money and I walked out that same night. I remember counting my cash in the bathroom stall and saying, ‘Jaclyn you can finally go, just go…’ and I did.”
Jaclyn’s energy is one of a shapeshifter. No matter where life takes her, she finds a way to adapt and move forward. After deciding she no longer wanted to pursue music, she felt an urge to try something new. She packed up her apartment in Gainesville and moved back to South Florida where she worked between a bar and a beauty brand to scrape up some money to buy a car and figure out what she wanted to do next. Intrigued by her time in the beauty industry, she was starting to wonder how to elevate the space.
“The beauty job was fun for a while but I wasn’t fully satisfied, so I started thinking about what else I could do. I had always loved fashion and wanted to bridge the worlds of arts and social impact. So, I registered my first business later that year and called it Rockntherunway and I used it as a platform to engage young people to register to vote.”
Rockntherunway was the beginning of Jaclyn’s path as an entrepreneur, truly forging her identity as a leader. She learned as she went along, turning each new experience into an opportunity to learn and further advance her career. During this time, she was studying the psychology behind human behavior and our need for connection, which became her intrinsic compass along the journey.
In her pursuits, she had a special way of connecting with anyone involved. For her runway shows, she hand wrote invitations to each of her guests with the hope they would attend. The hand-written letters paid off as she went on to produce larger runway shows in Miami and LA in addition to product and collection launch events. Over time, her experience working with numerous beauty and fashion brands led her to become a consultant for new companies seeking guidance in strategy and development.
Smacked in the Face by Life
“As an entrepreneur, when things go sideways, you’re always faced with this interesting reflection because you’re like, ‘I’m trying to work, i’m trying to make money, but i’m hitting brick walls.”
Although her career seemed to be blossoming, it wasn’t all that it seemed. If you meet Jaclyn, you will instantly be charmed by her charismatic personality and beautiful features. However, as an entrepreneur, her natural self did not always work in her favor. She experienced gender bias and discrimination from both women and men. While some men would make uncomfortable remarks, female managers discredited her experience and qualifications because they decided they did not like her.
“You know, as a woman you grow up and you constantly are being sort of, like, smacked in the face by life. You’re too pretty, you’re not pretty enough. You’re too skinny, you’re not skinny enough. And life sort of serves you this massive contradiction of what and who you’re supposed to be.”
When it came to men, Jaclyn had numerous experiences where a meeting was just an excuse to make a move. In one horrifying encounter in New York, one man told her she had “a lot of balls” and proceeded to grab her crotch. In another meeting with a skincare company, the man grabbed her face and told her they should go back to his office to “see the rest of the products.” Jaclyn excused herself to go to the restroom and ran out the door. Other stories include men touching her feet at meetings, telling her they’re watching her, and handing her their business card in case she “wants to take her career to the next level.”
“I felt really discouraged. In many of these meetings there was nothing that came out of it except for a lot of very uncomfortable and disheartening situations, which I’m sure many women can relate to.”
“I’ve understood from personal experiences the destructive nature of living as a version of ourselves. I developed a bit of an anti-conformist attitude in my entrepreneurialism. There is no easy business, but if it’s going to be hard, why not do it on your own terms? If you can re-write the rules, you can change the way the game is played.”
Jaclyn was successful in her endeavors as a consultant, appearing to live a marvelous life as she traveled around the world to pursue what was once her dream. Yet as she went deeper and deeper into that dream, she realized it was just an illusion. She put up with the occasional gender bias and disappointment because she was able to not take it too personally. However, she knew she was living a life in comfort by being in denial of what was happening. She knew in her heart that she wanted to do something that had the power to rewrite the rules, no matter how scary it felt to drop everything she started and chase this new dream.
“When I started Women of Wall Street, I wanted to do something more impactful and I was burnt out from disappointment. I had just walked away from a company I had loved, a long term relationship, and a life that was holding me down. My life had become all too predictable, too comfortable, and I had an inflated sense of security. It was when a close girlfriend said to me, ‘What are you so scared of? Lose everything, let it go’ that the light in me turned on.”
Women of Wall Street emerged out of her natural rebellion spirit that reignited once she realized the power of stepping into her true self, despite how uncomfortable and messy it would be. She was tired of being put down for being herself and she knew the only way to change this experience was to create a new one where other women could join along. Jaclyn understands the frustration of trying to fit into an unwelcoming space, so she created a new one where women can connect in a safe and supportive environment.
Women of Wall Street is not a brand as much as it is a movement to bring ambitious women together. WOW is rebelling against the stereotypes of a female leader by bringing the leaders together to support one another in their career as well as personal lives. The events hosted by Jaclyn create a space that encourages vulnerability. Women who attend these events have the opportunity to unbutton the pantsuit, take a breath, and get real with one another. The cut throat experience of fighting to prove oneself as a female leader is no more. Now is the time to come together and change the narrative for the future generation of women who will create and lead.
“The biggest challenge in life is holding onto who we are. If I can encourage more women out there to turn around and look back at their lives and appreciate their journeys, then I have done my job.”
A New Era of Female Empowerment: Women of Wall Street
The first WOW event was hosted in SoHo, NY where a group of incredibly successful women came together to share a meal over meaningful conversations and lots of laughs. In addition to building connections, these women found ways to collaborate and uplift each other professionally. Many women, since joining the network, have found ways to grow from the talent and services of others. They support one another and even find ways to make money together.
“It has been really great rounding up all of these incredible, accomplished, amazing, bold women. But I feel like our job in the long run is really going to be to pull all of the other women up with us so we can all stand together. A huge part of that is reaching out to the younger generation.”
As WOW evolves, Jaclyn’s vision is to continue building the community and uplifting a generation of younger women through mentorship programs. Whether it be a young girl fresh out of college, or an established CEO of a Fortune 500 company, the mission at WOW is to hold space for personal development and foster a new era of female leadership and empowerment.
“It’s going to take women forcing our way in, starting more businesses, and pulling more women into executive roles ourselves for the world to see what we are truly capable of.”
After a year away, Women of Wall Street returns to reunite with women across the US who will meet and support other like minded entrepreneurs and executives at change-making levels. We curate memorable experiences, but the real magic is the women who attend. To find out how to join Women of Wall Street or attend an event go to their website: www.wowwomenofwallstreet.com