The Reality of Women Entrepreneurs and How to Flourish in Business with Vivian and Dr. Tracy

Co-Founders of Flourish Media Conference, Vivian Olodun and Dr. Tracy Timberlake joined our Editor in Chief, Erikka Yvonne for a little Strut Talk! Everything a woman entrepreneur or aspiring entrepreneur needs to know about getting started and maintaining is right here. Vivian and Dr. Tracy also shares details on their upcoming Flourish Media Conference,

Read the interview below or listen to the podcast.

ERIKKA: First, we need to know what you are strutting in heels or sneakers? And why? 

Dr. Tracy Timberlake: Let me answer that question right off the bat. Because I will tell you right now, I’m definitely strutting in sneakers. I was an athlete my whole life. And now, I like to consider myself an after-thlete. But I’m very comfortable in sneakers. It makes me feel like I can maneuver. But secondly, you know, when I started my entrepreneurship journey, one of my main goals, and this is going to sound very bizarre, but one of my main goals in life was to be able to wear yoga pants every day, like because I had to dress up and wear businesses. I worked in a law school. And I was like, I do not want to learn this anymore. So, success for me was defined as being able to wear loungewear every single day. And I feel like sneakers will go very well with my yoga pants. 

Erikka: Yes, yes, I’m with you. My wardrobe is full of athleisure wear, joggers, and hoodies. So, I’m with you. What about you, Vivian?

Vivian: So I am strutting in sneakers but not by choice by obligation. I am currently 24 weeks pregnant with my second pregnancy, and I am struttin’ in tennis shoes because it’s the most comfortable thing for me to wear. And I’m embracing the more relaxed fashion. But truth be told, if I weren’t pregnant, I’d be struttin’ in heels. No doubt. I love a good heel. I love a body con dress funny; I’m sexy. I love bringing all the heat from top to bottom. That is my that’s where I feel the most comfortable. And I love to dress up when I was younger. I used to do beauty pageants and things. And I feel so confident and relaxed, completely dressed up. I like my hair to be done. I’m here with the makeup. Where is the Sephora gift card? I want it. I’m here for it, you know, but at the moment, I’m embracing the season that I’m in. 

ERIKKA: But you said something there because we enter different seasons all the time. You may have a season where you need to be a little bit more comfortable — in your sneakers. You have to hit the ground running. And you have seasons where you can get cute — wear makeup every day, throw your heels on, or throw your dress on. But each season is different. So you have to be ready for all of them.

Okay, so let’s get down to it. We know we are in the midst of what we’re all calling the great resignation. And women are building businesses left and right. 

Q: We also know that many of them do not last past their first couple of years. I want to ask you guys, why do you think that is?

Vivian: Flourish media is a multi-million dollar marketing firm based in Miami, Florida; we have the great pleasure of putting aside a portion of everything we make to reinvest in other women through our nonprofit. And what we discovered, after hosting the Flourish Media Conference for the last six years and raising $15 million in doing so, is that many people are not used to being entrepreneurs. I come from a military family; everybody in my family, uncles, aunts, and brother, are soldiers. I didn’t come from an environment where I had examples of what it means to be an entrepreneur. And I think that while many people may open businesses, there’s that special sauce that you get when you’re in the suitable environments and around the right tribe that can help show you what entrepreneurship has to offer and what it requires you. 

Dr. Tracy Timberlake: I’ve been a business coach for the latter part of the last decade, and I work with really high achieving women, primarily women who have PhDs and multiple master’s degrees. And so it’s not talent or capacity that is the issue. It is moving into a space that you are unfamiliar with that you cannot identify as an entrepreneur.

The women I work with are coming to the table with an extensive background in education, right? Traditional education has taught us how to be good employees. It doesn’t usually go to entrepreneurs. Traditional education teaches you how to sit in the classroom and raise your hand to be spoken to.

Raise your hand, so you can go to the bathroom, sit down, be quiet until somebody calls on your name. That’s what our education system teaches people; it doesn’t teach you to go out and do something on your own. It doesn’t teach you how to stand out. But it doesn’t teach you how to build something from scratch and stick with it. So part of the issue is that we have not been exposed. And ambition is predicated on exposure. So, if you’re not exposed to something different and only know one way of being successful, that looks like a college degree. 

Viv and I hold multiple degrees, so we value education. But that education has gotten us to where we are now. Not only because we leverage what we learned in the school system, but it’s because we simply knew how to stick with something and achieve outside of the box. And most people just don’t know how to think outside the box. 

Q. With both of you coming from non-traditional areas, how was that transition (into entrepreneurship) for you? 

Dr. Tracy Timberlake: I think there’s a couple of different kinds of people:

There’s the person they transition into entrepreneurship, and they go, okay, to become a full-time entrepreneur, I need to make money and have six months of my salary saved, and then I’m going to do it, right. There’s that person.

  1. There’s the person they transition into entrepreneurship, and they go, okay, to become a full-time entrepreneur, I need to make money and have six months of my salary saved, and then I’m going to do it, right. There’s that person. 
  2. And then some people like me, and Vivian, the same thing, we didn’t have this six months’ worth of savings, this grand plan, we just are like, You know what, we don’t like this anymore, and we’re going to leave. 

And then the same thing that got us to be successful in other areas of life, which is that entrepreneurship in my eyes when I quit my job, I didn’t know failure. That wasn’t even an option. It wasn’t even on my radar. Like there wasn’t an” Oh, what if it doesn’t work?” That didn’t even cross my mind. It was more like, “oh, I want to do this. So I’m going to do it.: And I’m going to do it in the same way that I’ve done everything else in my life. Awesome, and 

ERIKKA: Vivian for you, with your family, being military and that discipline they have. Do you think that any of that played a role in the structure you’re able to develop? As an entrepreneur?

VIVIAN: 100% I think one of the special sauces when it comes to running a business for multiple years is that commitment because commitment, discipline, is what shows up when you’re tired. When the talent isn’t there, you have to develop a new skill or learn how to delegate to others. Being able to show up every single day, on the days when you feel the lowest is a vital thing when you are an entrepreneur.

And I think that when it comes to jumping into entrepreneurship, it was so innate to me.

When I was in college, we started a fashion club. And during the fashion club, we put on fashion shows, and I decided to go into a boutique one day, and I couldn’t afford a dress, and I looked at the dress so hard. And I said you know what? If we put on a fashion show at the school, will you give me this dress for free? It’s just a part of being resourceful. And when you are innovative and constantly looking for ways to solve problems, you’re going to make money. 

And what happened for me with that dress, which started me on the road to entrepreneurship was we held the fashion show, and we made so much money that the school wasn’t able to hold the money because I was a student, you know, with a student program, legally, they couldn’t hold the funds. They told me you have to open a business bank account; you can’t keep this money here. 

Dr. Tracy and I are so focused on helping people clearly identify what problems exist in the world.cAnd how is your business going to solve that. That’s your only responsibility as a business owner. We’re coming from a marketing perspective; you have to do two things, you have to be able to identify the problem you solve. And then, you have to educate your audience on why you are the right person to solve the problem.

ERIKKA: I know you also mentioned that neither of you had a plan when you quit your job or six months saved up, which leads me to the conversation of funding for women entrepreneurs and some of the resources that help them get off the ground. 

Q: What things do you feel like startups and women entrepreneurs should have in place to get some of that funding? And where should they look? 

Vivian: First and foremost, you should never judge where your money is coming from. Because I think a lot of us when we want to start a business, you’re faced with that idea that I work for someone else, I’m an employee. Instead, think of your job or the career that you have as your very first investor. They are paying you to get educated, paying you for on-the-job training, paying you to figure out what you don’t like doing so that when you leave and start your own business, you don’t do the same thing. It’s a powerful position to be in that space. When you have a job and have a vision and clarity, you want to open a business. It’s a very special place. 

Dr. Tracy Timberlake: When it comes to funding your business, yes, your employer is your first financier because they’re, making sure that you have a paycheck that allows you to take care of what you need. For many people, that’s required; they want to have the peace of mind that their bills will be paid before they start to move forward in other areas of their entrepreneurial journey or their business. And that’s 100% perfectly fine. 

However, once you do venture out into entrepreneurship, many people believe that you need to have the funds yourself, and those funds need to be in your bank account. That it needs to be funded by you. And just as a principle across the board, if you look at every wealthy person, they’re not funding their business ventures, they’re getting investors, sometimes they’re getting business lines of credit. I mean, there are so many different available options. It is a middle-class mindset to believe that you need to save up to do everything yourself. 

A wealthy person will go okay, who has this money because I need to figure out how to get it. And that’s one of the things that we teach at the Flourish Media Conference, getting people in front of other avenues that allow for them to get capital, whether it’s an investor who can give you 100,000 200,000 A million dollars for your business venture, or whether it’s, partnering with people that we’ve partnered before like Capital One who has extensive opportunities for entrepreneurs and small businesses to have business lines of credit. 

There are so many ways to get money; your ability to call money in is not just predicated on what you can do. It’s also on the network and your ability to find things when you need to see them.

Dr. Tracy Timberlake

Vivian: I need everybody to understand this. The power of leveraging your community, leveraging the network, that you are a part of the community, the resources available in the world because there is money everywhere. It depends on your ability to talk about what you do. And it is so powerful at the Flourish Media Conference; our theme this year is AMPLIFY because we want to inject some confidence into every single person who attends the Flourish Media Conference, February 17 and 18th in Miami, Florida. We want you to feel comfortable talking about your business, to a billionaire, to a bank, to an angel investor, to a local community program director, because when you can get pumped up about your business, other people feel that enthusiasm and they want to be on the winning team, which is your team. 

Q. Can you give us more information about this Flourish Media Conference?

Vivian: Oh, it is magnificent. I mean, and I can say that, humbly, because the women who have participated in our conference over this last six years have gone on to have products in Goop, Target, Marshalls, and Urban Outfitters. They’ve gone on to get grants and funding. They’re working with different public figures; they have just catapulted. They’ve been on Shark Tank and closed deals with Kevin O’Leary, Mr. Wonderful himself, I mean, the network that you are a part of simply by being in the room at the Flourish Media Conference is phenomenal, 

In addition to the fact that you’re able to build a relationship with willing investors, funders, and alternative funding programs so that you can grow your business. These investors who commit to being present at our conference are looking for companies at different levels. They’re looking for service-based business and businesses and product-based businesses to invest in. And they are looking and open to hearing what you asked for because Dr. Tracy, yes or no, don’t the women always ask for less than what the investors.

Dr. Tracy Timberlake: Always, and I think that’s something we really need to talk about. As women, we, as business owners, believe that we need to bootstrap everything. There are billions of dollars available for women-owned businesses for minority-owned businesses. We just don’t know how to access it. Because we’re operating according to our limited mindset. 

You have to expand your capacity to know where money is coming from and how wealthy people operate. Wealthy people look for other wealthy people, to give them money for stuff. 

  • start new production companies 
  • make movies to build a new product
  • have a new system in place to get an app

They’re not out here doing it on their own. They’re thinking about how to get other people involved. That is a part of being a CEO, your job as a CEO of your company is to bring money through the door, and your ability to do it may be limited If you’re not willing to go out and network with people who have more money than you. 

ERIKKA: Okay, so networking. How do you even develop the confidence to do that? If you already have this mindset, you’re scared or fearful of rejection somehow.

Q. How do you develop that confidence to network above wealthier people than you and feel like you belong in that same space? 

Vivian: Opportunities like the Flourish Media Conference. So there’s a statistic that was shared once that CEOs or people running multi-million dollar companies and billionaires usually attend up to 10 different conferences per year, from the introverted of the introverted with the Mark Zuckerberg’s of the world. That is a special sauce.

That’s a thing that businesses do not know that is available to them; you need a network of other business owners who understand what’s going on; you need to be in that environment. And the more you do it, the more comfortable you will be because you’ll find that when you go to an event like the Flourish Media Conference, you’ll find that the room isn’t intimidating. People want to talk to you. They are just as passionate about their businesses as you are about yours. And they want to sit down and talk to you for hours and days, about systems about how you’re using Shopify, about what lawyer you picked. 

That’s something that’s missing when you’re trying to run a business by yourself because your Uncle Auntie, Mama, loves you. They want you to do well. But, can they talk to you about what’s the appropriate insurance for a business? 

Dr. Tracy Timberlake: It’s okay to be a little bit afraid. It’s okay to be a little bit shy. It’s okay not to have confidence in the beginning. Everybody feels that way. Sometimes, we think we go into these environments and are the only ones having these problems. Not at all. The thing that separates successful people from those who don’t get to those high levels of success is the willingness to show up for it. 

  • Can you still show up when you’re scared?
  • Can you still have a conversation when you don’t feel fully confident? 
  • Can you still be in the room of all of these people and normalize what it looks like in an environment of successful people? 

That’s going to be the difference between where you are now and where it is you want to go? You have to be able to do things scared, to do something when you’re not competent. Like Vivian said earlier, do it when you’re not motivated. 

Those emotions, not being motivated, fear, and lack of comfort, are temporary places. If you recognize this is temporary. Tell yourself: Just for right now, let me just be willing to get over it today. And I’ll worry about tomorrow, tomorrow. 

It’s you showing up; it’s going to make all the difference. 

ERIKKA: So, much of what we talked about today and touched on goes back to mindset. I think that’s also a big part of becoming an entrepreneur, instead of a man or woman.

Q. How did you guys cultivate or shift your mindset and your processes of becoming multi-millionaires?

Vivian: When I was thinking about changing my mindset, a lot of it had to be very clear about what I didn’t want. I knew that I didn’t want to be at a job where I felt undervalued and underemployed; in an environment where I had to think twice about doing something nice for the people that I love. I knew that I wanted to take vacations and visit because my family is from Panama, Nigeria. I’m a military brat — my family is all over the world. I decided to leave my last corporate job in Machu Picchu, Peru, looking at a mountain.

And I said to. Myself, “You know what, in the end, you went through too much to get these little sad three days off. Here for this to take this in. This is not right. This is not the life you want to live? Do you want to live the rest of your life with other people having control over your calendar? And your flexibility?” The answer is simply no. I do things actively every day to move away from that environment, period.

Dr. Tracy Timberlake: Anything about mindset is primarily what I teach people because it’s going to be the difference between who you are now and who you’re going to be later. What people don’t recognize is that you have to change your identity. If you have always been an employee, and now you’re moving into a space of entrepreneurship, you have integrated a new identity; you’re still operating according to an answer to an employee. 

If you’re making $85,000 a year, and you’re telling yourself you want to make a quarter of a million, you’re not making decisions based on a quarter of a million-dollar income; you’re making decisions based on $80,000. Because that’s what you know how to do. If you don’t change your mindset, you’re not going to get to where you want to go because you’re unwilling to adopt a new identity. 

ERIKKA: Oh, that’s good. That’s good. Okay, so back to the conference. 

Q. How can people sign up? Is there is registration still open? And if so, how can our listeners sign up to attend? 

Registration is most certainly open. You can go to We have three options to participate: 

  1. You can join us in person; both days of tickets are available, regular price tickets are $600. 
  2. If you’d like to be with us, just for one of the two days, a one-day pass is $350. 
  3. If you act too slow, then you’ll have to get a virtual pass. And that virtual ticket is available right now on pre-sale for $30. It will show a number of the different segments on both days. 

Q. What are five ways women entrepreneurs can be catalysts for change? 

Vivian: Ooh, what a great question…

  1. Invest in herself. Investing in yourself is the best investment that you will ever make in your life. Whether that’s in your education, in yourself carrying your physical body, in the way you eat, your nutrition, or the way you show up in the world. 
  2. Choose to be in environments where you can flourish. If you are asked to participate in an educational setting, show up, if it costs money, $60 $20 $5, pay the money and be there, you’d be surprised what kind of exponential return on investment you will always get by growing your network with the right people and with intention. 
  3. Get your mindset around money together. Your money mindset affects every single way that you spend and receive money. We have created Made for Millions Mastermind, a mastermind for women business owners, that we have to flourish media. It’s for people who want to move their business into seven and eight figures. One of the challenges for people who have businesses still making five figures is that they’re most likely charging too little for the service they’re providing. That has a lot to do with how you would spend money; maybe you’ll say I’m not going to charge X number of dollars because I wouldn’t pay that for that service or for that product. But guess what, there’s a car that exists, that is half a million dollars. Why? Because there’s somebody who will pay. You can play at any level; you can participate at any level. 
  4. I am not doing things yourself. I’m living in this melanated body. And I’ve been receiving the same messages for many, many years, that I’m supposed to be a strong black woman who could do everything myself, and I never need help. And that’s a lie from the pit of hell. Because you know, what, if we only required ourselves, why would we be put on this planet with so many other people? Why? We are here to work together to do things to be collaborative and open to receiving help. Get used to be clear about how people can help you. And Honey, let them help you. Let people help you. 
  5. Do things that you enjoy. Structure your business so that you can enjoy this entrepreneurial journey. It is one of the most exciting, challenging things that you will probably ever do in your life. And when you’re building your business, you’re going to have to be able to have a good time, find the joy in doing those small, mundane things, and then find the joy in those significant challenges and those big accomplishments that you have. Remember to celebrate your small wins. Remember to have fun in your business. 

Q. Last piece of advice

Dr. Tracy Timberlake: Money loves speed. Learn how to take action quickly; you have to go from idea to execution as soon as possible. listening to podcasts 

Vivian: You are made for millions. No matter what is going on. The skill…the talent you have is set up to take care of you in all aspects of your area. The things you can bring to the table are worth millions. Recognize that you have the capacity and the ability to make millions of dollars from the things you already know. And it’s up to you to take action on those things. I hope to see you at the Flourish Media Conference on February 17 and 18th. So, you can get around people and environments that help you bring those things to fruition and help those things flourish.