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Toni Gilliard is a native of New York City that has been a resident of Charleston, SC, for nearly two decades. Gilliard is a well-respected and successful immigration attorney and real estate agent. She is also an entrepreneur, and her most important role, single mother of two. Remember her name, because, although she wears many tiara’s, Gilliard is preparing to tip the scales in a majority male-dominated industry and not taking “NO” as an option.

Born in Bronx, New York, and raised in Mid-town Manhattan in Amsterdam Houses with her mother and siblings, Gilliard was always ambitious and determined to be a successful icon since her youth. Upon graduating high school, she journeyed to Trinity University, an all women institution in Washington, DC for her undergraduate degree in Political Science and English Literature. While at Trinity, Gilliard pledged Delta Sigma Theta Sorority.  Following, she attained her law degree at the University of Maryland. When asked what made her choose the path of law, she responded, “law chose me.” Gilliard shared that she has always been an artist at heart. Her dream was to become an artist, and, maybe dance for Alvin Ailey, a famous dance company based out of New York City. As a child, her mother would tell her she was going to be a lawyer. Gilliard’s active participation in the Student government and the debate team at school was only the stepping stone to her career as an attorney. She migrated to anything political in her early years.  Gilliard recalled her time in college, while students would enjoy their Spring break by going to Freaknik and other college week parties, she chose to volunteer and live on a migrant farm in Apopka, Florida picking produce. That experience helped open her eyes to the world of immigration and made her want to practice immigration law. As an experienced bilingual, Gilliard recognized that her skills could be of great service to the immigration community.


Aside from her legal practice, Gilliard has been in real estate for the past three years, specializing in residential and commercial properties. She loves her new role as an agent, and, although Gilliard enjoys practicing law, she shares how she is no longer in love with it, and plans to do real estate full-time. Gilliard shared, in this political climate, immigration law started to become more depressing and challenging, trying to save people from being deported and separated from their families. She started losing sleep and found herself becoming more depressed because, once upon a time, specific issues she could help with, today's administration makes it more challenging to assist immigrants. Gilliard also shared the work began to take a toll on her family, as well because of the extended hours and stress. Gilliard finds that in real estate, she can still be of service and utilize her legal skills to not only help immigrants but all nationalities. Because of her legal background, clients are comfortable working with Gilliard. Her legal background allows Gilliard to explain the legal jargon if she has court-ordered sales and contracts, and make better negotiations. Gilliard is passionate about helping people build generational wealth and educating them about the process of investing in property and their businesses.


Tipping the Scales with Tipsy Lady

While vacationing in Barbados, Gilliard was doing some soul-searching on how to generate wealth without being transactional, where she would have to exchange or interact with people in one setting. She wanted to establish a product that she was passionate about, and others can enjoy it. Suddenly, she thought about a rum punch that her family request she makes during the holiday season. Because of the maintenance and the cost of ingredients, Gilliard thought about creating a packaged, ready-to-drink rum punch, where consumers can buy the product off the shelf, ready to enjoy. The rum punch was the first product of Tipsy Lady Cocktails, which are ready-to-drink Caribbean inspired cocktails.

In her research, Gilliard discovered that developing the rum punch as a product would have been too expensive to put on the market, where it would make a decent profit.  Soon after, she thought about Bossy Mom and how she enjoyed creating meals and hosting brunches. During those brunches, Gilliard usually serve mimosas. The mimosas were still in line with her vision of the Caribbean inspired and being authentic to herself. So, she merged her two favorite components, prosecco, and Caribbean juices, and created Tipsy Lady Mimosas.  A ready-to-drink premium mimosa, which comes in three different flavors: mango, pineapple, and classic.

When someone hears the name Tipsy Lady, the first thing that may come to mind is getting intoxicated by alcohol. Gilliard says that is not the meaning behind the catchy title. Tipsy Lady means tipping the scales in the alcohol industry that is majority a male-dominating business. As Gilliard prepared to create Tipsy Lady, she made a few phone calls in search of mentors who were already in the alcohol industry. Most of whom she contacted were men. The questions they asked her were, are you married? Do you have children? And, are you single? If she answered any of those questions with a yes, they opted against working with Gilliard because they felt, as a single mother, she would not have time to market her brand, and they will lose a lot of money taking a chance on her. Also, Gilliard read articles that stated, the questions that the men asked her were common questions asked to women who would pitch ideas to stores and distributors.

After Gilliard did not receive any help from her contacts, she decided to create a seat at the table for herself. She participated in certification classes, joined various organizations that coached her on marketing her product, and made her own contact with distributors and suppliers. Gilliard tipped the scales in the alcohol and beverage industry, making room at the table for more women to hold their own and to join her.

Tipsy Lady ready-to-drink mimosas will be available in major supermarkets around the country very soon.

Gilliard's words of wisdom to everyone who wants success is,“The very thing you are afraid of will free you. God blesses everyone with a skill and an asset. You are your asset. There is something within yourself that will grant you financial freedom, even if it starts as your side hustle, which can be your ticket to financial freedom. Always be authentic and true to yourself, do what you love, and the money will come.”

Tipping the Scales with Toni Gilliard: Work
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