ethically diverse woman in yellow sweater

Meet Trudi Lebron, CEO of ScriptFlip!, a diversity, equity, and inclusion consultancy.

Keith Claytor

One of the most important questions any entrepreneur can ask herself in today’s landscape is: “How inclusive is the business I’m building?” 

Diversity isn’t just an ethical issue, it’s one that affects economics, as well. Diverse companies are 70% better at capturing new markets since diverse teams know how to reach diverse audiences. As it turns out, profits and impact can co-exist beautifully.

Case in point: Trudi Lebron, CEO of ScriptFlip!, a diversity, equity, and inclusion consultancy. “When I entered the world of entrepreneurship, the lack of representation across the industry was shocking,” says Lebron, who is biracial. “So I began offering support to coaches while also teaching impact-driven business practices. But it took years before people saw the true value of my work.”

Lebron is no stranger to flipping scripts. At 16, she became a mother—for the second time. “People, some of whom were total strangers, told me I was going to be poor and a drain on the system. But they were wrong,” says Lebron, whose parents helped her raise her two sons. In 2020, Lebron’s company made seven-figures—and at 39 years young, this PhD candidate in Social Psychology is just getting started.

In this exclusive interview, Lebron shares her journey from high school dropout to highly successful entrepreneur, the tidal wave of inclusive change coming to entrepreneurship, and how to run a profitable business that prioritizes impact.

Celinne Da Costa: Tell us about your background.

Trudi Lebron: I grew up knowing that we all have a responsibility to help others. My father is Afro-Latino and worked in the military. He was focused on structure and order and he was super practical. My mother is white and worked as an administrator for a non-profit so she was out in the streets advocating for everything. They worked hard, but we were the working poor. I had a regular diet of tomato soup and grilled cheese sandwiches from a hot plate because I spent my adolescence living in an apartment that didn’t have a stove. 

We lived in the inner city in Connecticut and I remember always having this feeling of not belonging. There weren’t a lot of biracial children in our community and I had this exhausting burden of literally defending my identity to the other kids. People didn’t believe my father was my father because he is darker-skinned than me and I didn’t speak Spanish well. 

When you’re white, you just get to be white. You don’t have to defend anything. When you’re mixed, suddenly you have all of this explaining to do. So much of my childhood experiences inform the diversity and inclusion work that I do today.

Da Costa: How did becoming a teen mom impact you?

Lebron: Things got real for me, real quick. I had two boys who were counting on me for everything. I homeschooled myself through high school and enrolled in community college. For years, my life was a steady routine of taking my kids to school or daycare, attending classes during the day, working afternoons and evenings, caring for my kids, and staying up all night to do homework.

After I graduated, I met the love of my life who helped me follow my dreams. I went on to get my master’s in psychology and started working at non-profit organizations. But I quickly realized that while non-profits in youth and community services do a good job putting band-aids on situations we weren’t creating permanent solutions. There were no transformations happening—and there were so many broken systems. 

diverse woman sitting on the steps of a street

“It occurred to me that people in the entrepreneurial world needed to re-evaluate their company’s … [+] core values on their way to making change. So that’s what I focused my business on: that intersection between entrepreneurship, inclusivity and impact.”

Keith Claytor

Da Costa: How did you transition from the nonprofit world to entrepreneurship?

Lebron: At one point, I was working at a high school helping high-risk students graduate. One of the rules was that students who showed up late couldn’t get a free breakfast. I was written up one morning because a pregnant student in my caseload came in late and I got her something to eat. It hit me hard that our values were completely out of alignment with our goals. 

I recognized that I wasn’t going to be able to fix the system from the inside out. I’d have to do it by starting my own business. I started listening to podcasts on entrepreneurship to figuring out everything from how to price my services to how to build an email list. 

On the shows, people would say things that I hadn’t heard before about money. That it could be easy to come by. That really blew my mind because I grew up thinking it was hard to get and might actually be bad. 

I also quickly noticed that the entrepreneurial world wasn’t very diverse. It occurred to me that people in the entrepreneurial world needed to re-evaluate their company’s core values on their way to making change. So that’s what I focused my business on: that intersection between entrepreneurship, inclusivity, and impact.

I continued on full-time at my job but started working on my website from my kitchen table at night and meeting with clients on my vacation days. I had built a name for myself locally and was in demand for diversity education and helping entrepreneurs build businesses with a social justice focus. As I began building relationships in the online world, hosting a podcast, and leading the conversation around race equity and diversity, people started to notice. By the end of 2016, I had left my job and was working full time on my business.

Da Costa: What was working on diversity, equity, and inclusion like at the start of your business?

Lebron: For years, I was working on faith and hustle. I felt like I was screaming and no one was listening. I was basically saying, “Hey, I smell smoke in the back of the building!” But no one realized that lack of diversity was going to eventually become a raging fire. 

Honestly, after two years, I almost threw my business away and applied for a regular job. The company was extremely profitable but I knew I could get a six-figure executive director job somewhere and not feel exhausted all the time from constantly trying to convince entrepreneurs that diversity, equity, and inclusion were important.

I also struggled with a serious case of imposter syndrome. I was the first person in my family or group of friends to be an entrepreneur. The people closest to me didn’t understand what I was doing. And very few people in the entrepreneurial world that I met at conferences and events looked like me. Once again, I didn’t feel like I fit in, but I knew there was a deeply important purpose behind what I was doing. 

Da Costa: When did your business start to catch on like wildfire?

Lebron: Last year, after the death of George Floyd and the rise of the Black Lives Matters movement, some entrepreneurs made some key missteps in addressing his killing. After an online incident that occurred on a Saturday, I decided to call an “Emergency Meeting” on a Sunday around diversity, equity, and inclusion in our industry. 

We had more than 600 people live on the call. I had to keep upgrading my Zoom account status so more people could join. Since then, we’ve had more than 2,000 people purchase my workshop. My business had been bringing in multiple-six figures for years, but this one product did that alone last year. 

After five years of waiting, everyone from new entrepreneurs to established ones were ready to do organizational overhauls and make sure their values were coming through in their business. I was there to help them. 


Da Costa: What advice do you have for other entrepreneurs who feel like they’re doing important work but not enough people are listening?

Lebron: First of all, if you have a worthy cause that you feel strongly about, don’t switch your niche every couple of months or call it quits. Just keep showing up and recognize that you’re playing the long game on this one. The only way people will recognize you for who you are, the things you talk about, and what you stand for, is if you keep telling them. 

You’ll also need to build relationships. I went to every conference that I could so that people saw my face, shook my hand, and heard what I had to say. I reached out to people and became a part of the conversation across communities in a genuine and helpful way. That’s how people knew who to come to when they were ready to have those tough conversations around inclusion.

Finally, stay ready. I had been waiting for the moment when the entrepreneurial world started taking diversity, equity, and inclusion seriously. I had been preparing my whole life for this. As soon as it happened, I jumped on it. Once people are willing to listen to you, you have to be ready to jump in, too.

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Roland Millaner