“Entrepreneur, meet investor; investor, meet entrepreneur.”
That, put simply, was what was going on over the weekend during the 10th Annual Flourish Media Conference in which small- and prospective-business owners gathered to receive advice, attend workshops, and connect with potential investors who think their ideas could make a profit for everyone.
It started with a lunch ten years ago with soon-to-be Flourish Media co-founder Vivian Olodun and a business investor.
Flourish Media co-founders Tracy Timberlake and Vivian Olodun sit with Sandy Fernandez of Intercredit Bank, a Flourish Media Conference title sponsor.
A conversation about a woman business owner brought some revelations from the unnamed investor.
“He started rattling off all these statistics about what happens when women get investment. When women are invested in they are eight times more likely to be successful in their businesses,” Olodun said.
Attendees of the Flourish Media Conference.
Olodun recalled the man saying the reason it’s hard for women to find investors is because investors want to see themselves in the entrepreneur.
So Olodun had a question for him: “What would you do if you could invest into women and meet with them? Would you do that?”
Olodun said that after working with co-founder Tracy Timberlake, they soon had 26 different investors willing to meet women entrepreneurs for the first conference.
Attendees of the Flourish Media Conference had the opportunity to attend workshops and meet investors.
“And that is how the Flourish Media Conference was born,” Olodun said. “We are a matchmaking weekend for angel investors and women business owners.”
The conference was just the beginning
When the conference was over, Olodun and Timberlake found their work wasn’t done yet.
Miami-Dade County Mayor Daniella Levine Cava welcomes the attendees.
“We wanted to help women, we wanted to help small businesses, and we did that,” Timberlake explained. But then, “People wanted to know more, like, ‘OK, well, what do we do now? This is such a great experience. You can’t just leave us to our own devices after this.’”
“And that’s how Flourish Media, the company, got started, to where we started having events throughout the year — our mastermind courses, classes, workshops that we’ve gotten a chance to host in a variety of different spaces,” Timberlake said. “But it really was birthed out of the ask. It was the ask of all of the women that were at the conference. We definitely didn’t intend to start a business that’s now 10 years in the running.”
A proclamation from the county declaring Feb. 21 as “Behind The Leaf Day.”
Olodun and Timberlake said they were supposed to work together just once, but the success of the conference changed things.
“Both of us being here in South Florida and being in the entrepreneurial space, first of all, it’s rare,” Timberlake said. “But it’s also rare when you get a chance to collaborate and it ends up being successful.”
The business of business
So what exactly does Flourish Media do?
Olodun described the company as a marketing training and development agency.
“We focus on teaching funders, founders and entrepreneurs, and business owners how to utilize marketing in order to grow their visibility in the digital space and in the real world,” Olodun said.
Timberlake stressed the importance of creating access between entrepreneurs and investors.
“(Flourish Media) creates this ecosystem so that entrepreneurs aren’t building in a silo,” she said. “They’re not in isolation, but they’re actually in relationship, in dialogue, in conversation with peers, with mentors, with investors, with other operators who really understand the context of what they’re trying to do.”
Timberlake said the conference is something a lot of people look forward to.
“Everyone is always really excited about this weekend because they know it’s going to be amazing,” Timberlake said. “I think you’re also going to be given so much information to take in because you realize that there is a whole world of business, funding, branding, visibility that sometimes we don’t get a chance to get access to, or we’re unaware of, until you’re really inside of these high-level spaces.”
The conferences include an investor pitch segment; on-site women-owned vendors; workshops and panels; and networking with leaders and investors.
Guidebooks illustrated the stages of business success.
Steps everyone takes
Olodun explained the process attendees go through.
“We have something called a Seasons Quiz,” Olodun said. “Every single person who participates in our ecosystem takes the Seasons Quiz, and it helps for us to identify what are going to be the big wins for you. How do you position yourself for investor readiness?”
Timberlake says most first-time attendees likely have two takeaways:
“I think you’re going to be confronted with yourself. You’re going to realize that, number one, you probably want to be a part of the community. And then number two, your ambition is going to increase because you’re going to realize what possibility looks like based on the many success stories that we will highlight over the weekend, as well as the people that are coming in with their own desires and ambitions.”
Success stories
Speaking of success stories, the executives have an impressive list:
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Sainte Billings, the founder of Ampliara, a financial services firm. They said Billings was able to increase her revenue to $50,000 a month;
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Kreyol Essence, whose founder made her pitch at the 2019 conference and, after feedback from investors and funders, went on Shark Tank and closed a deal with Kevin O’Leary. Her skin care products are now available at Ulta Beauty and other major stores;
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Home health care business Rest Assured Care, whose founder, according to Olodun, was able to design and build a foundation for her business, which three different companies quickly asked to buy;
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Karlene Scarlett, who after participating in a Flourish Media conference, “within one year, was able to leave her job, replace her salary, and actually increase her salary by $10,000 per month,” said Olodun.
“So, yeah, we have a lot of success stories,” Olodun said.
Getting help
Putting on the conference is a lot of work, for which Olodun and Timberlake share the credit.
“Thankfully, we have a really good team,” Timberlake said. “And so they’re sort of handling some of the logistical things.”
The Behind The Leaf Board of Directors.
They also credit title sponsors Sandy Fernandez of InterCredit Bank and Kara Vaval of Vaval Law.
“They believe in the work that we do and make the largest donations for impact for the year, and so we always want to highlight their support of the work that we do for the community,” Timberlake said.
Behind The Leaf
The executives are also proud of Behind The Leaf, the firm’s nonprofit arm.
Behind The Leaf co-founders Tracy Timberlake and Vivian Olodun hold a proclamation from the county declaring Feb. 21 as “Behind The Leaf Day.”
Behind The Leaf encourages diverse women to see small business ownership as an opportunity for economic advancement. It offers educational products, workshops, and networking events. The Mayor’s Office of Miami-Dade County officially proclaimed Feb. 21 as “Behind The Leaf Day”
“We said we’re going to open a nonprofit so that we have a container to serve the community, and so all of our community work is done through Behind The Leaf,” Olodun explained. “When people buy the Flourish membership, they are making a donation to Behind the Leaf. And that is how Behind The Leaf is 100% self-operated and self-funded.”



