Cassandra chatted with Forbes Women on the struggles that conceived her company. She shares with Moira, the Executive Vice President of Forbes, how she channeled her pain into a profitable business rooted in passion and community.

Moira: Can you talk about your early days? Why did you decide to talk about your journey and struggles on YouTube? Was it difficult to share the real you?

Cassandra: It wasn’t just a struggle; it was a secret. The first YouTube video that blew up was the on where I exposed my bare skin, but most people don’t know that I had to film that twice. I deleted the footage each time because I was terrified. 

Growing up, I was called things like “pizza face” and “connect the dots.'' The bullying was constant. I remember wearing a white shirt to a peppy rally one day. As we were going back to class, people started pointing at me. I had leaned back on the bleachers during the pep rally, and all of my acne had burst. Moments like that reverberated within and exacerbated my emotional and physical condition. It was exhausting to try and cover myself up with makeup every day just to feel worthy of existing. I began to let out this pain on YouTube. In 2010, YouTube wasn’t that huge of a thing. So, I just thought of making videos showing how I got through the day. Honestly,  I just hoped it would reach someone that needed it. 

Moira: What was the impetus for not only sharing your story but for taking the huge step of showing your skin?

Cassandra: I think it was frustration. When I started modeling, the makeup artist would tell me to come without makeup, but I would still wear foundation. It felt like I was only getting booked because of photoshop and good lighting. And by the time the photo came out, it didn’t even look like me. I almost felt like I was living a double life. Nobody knew that I had seen 23 doctors and dermatologists to help me with my skin. No one knew that I was hurting myself, hating myself, and feeling worthless. And yet, I was parading around on a runway like some image of beauty. That felt very hypocritical to me. I felt very done with it, and YouTube was a place that I could go to.

Moira: Can you talk about the reaction to your first video? What was realizing its impact like?

Cassandra: When I first posted it, I intentionally did not look at the internet for four months. A lot was going on. I was in an abusive relationship. I had been struggling with my mental health. I was hurting myself because I didn’t have the tools necessary to embrace myself. And overall, I didn’t know how to ask for help. When you grow up being called connect the dots, freak of nature, or the walking infection, you don’t feel worthy of help or empathy from people. So, I didn’t expect the internet to be nice to me, especially in 2010. I didn’t look at the video until March of the next year, and when I did, I broke down. 

In five years, it was probably my first time feeling humanity. Instead of people telling me that I was ugly and unworthy, people were telling me that they had the same struggle. They were saying “you make me feel less alone”  All of a sudden, I thought - “maybe this is more normal than we think. We were all embarrassed, but we’re just not talking about it.” 

Moira: How did you continue to build on this conversation on YouTube?

Cassandra: At the time, YouTube provided a small community of like-minded people going through the same things. There was one woman who told me that she hadn't shown her boyfriend of two years her real skin. But then, she decided to show him. And guess what? He didn’t break up with her, he married her, and now they have a kid. From then on, I started trying to understand what it meant to have this community and what it meant to help other women with their skin and self-esteem. Our skin has multiple layers just like us, and I wondered how skincare could come into play with self-acceptance. 

This question fueled a passion within me, and it also came from a pain that I had felt previously. In the beginning, I didn’t know how to turn this passion into a business. I made a lot of mistakes, and I listened to a lot of people. Unfortunately, not everyone has your best interest in mind. 

Moira: When you look at those mistakes or learning opportunities, what do you think was the most valuable or common mistake you made. Was connecting to an audience and building a community on a platform that’s so established challenging?

Cassandra: Straying away from authenticity was probably the mistake I learned the most from. I had a manager once who someone had recommended to me. She was getting me to do promotions that I didn’t agree with. She’s was getting me to promote chapsticks and steakhouse. I don’t hate chapstick, but I believe in cruelty-free and vegan things. I also don’t eat meat because I believe in consent. I felt like I was living a lie because these types of promotional deals did not represent who I was. 

I had only started because I wanted to help people who felt the way I felt. I wanted to fight against the idea that acne made us ugly or unworthy. I wanted to reinforce the fact that acne is a human condition. That’s where my passion was. So, I thought to myself - “Why am I straying away from it?” 

Along the way, I saw others selling out, and this was a hard lesson too - that not everyone will stay the course. I had to learn commitment. I wanted to make a positive influence and sticking to those core values of honesty, intellect, and community was what truly kept me going.

 

Moira: What do you think is the biggest misconception that people have about the business of influencing. What does it truly mean to build a brand around influence?

Cassandra: I don’t think people know how it works behind the scenes. People don’t realize that you can have a million-dollar business without selling any products. It’s kind of like a media outlet or newspaper. If a brand wants to run an ad on a news platform, prices will range depending on where the ad is placed in the paper. The brand has to pay for that exposure. In this digital age, it’s a lot easier to track exposure and how many people are purchasing the item in the ad. 

However, I can be selective about the  products that are right for our platform, and I can negotiate the amount of exposure our platform will give them. 

Then, there are affiliate commissions too. Even by just posting videos, YouTube and Facebook will put ads on that video content. This is also a source of revenue. Furthermore, there are commercial streams. By posting content that people think people deem valuable enough to watch, you can earn monetary compensation. And most of all, you can build your community.

 

Moira: Can you explain what it’s like to have a business model around community? How do you monetize while simultaneously staying authentic to your values?

Cassandra: It starts with commitment. For example, there was an affiliate that would reach out to me and say - "if you promote this palette, you can earn X amount of money." I was like - "I don’t agree with those ingredients."

For us, we use a company called narrative which is another 30 under 30 business. She built this entire affiliate platform that allows influencers to talk about products they love. When someone shops that specific product, we get 1% or 5%. That allows us to keep that authenticity but maintain a revenue stream, pay employees, and pay for benefits.

Moira: How have you learned to develop a content strategy around narrative and conversation?

Cassandra: It comes down to knowing what matters to you and speaking about it. It’s also about knowing what works and knowing what doesn’t.  We have nine video editors, we couldn’t do any of this without them. When I started, it was me behind a computer for twelve hours a day. While it looks effortless, that’s kind of the point. When you want a recommendation, it’s personal. YouTube started out as this peek into someone’s personal life Because of that, influencers are much more accessible and real than the traditional celebrity who always looks perfect and has a mysterious life. 

Our content is homey because people have a social connection my acne journey and being able to ask for help. That goes back to my original goal of presenting something real. Content stratgy can be as simple as having an open conversation along with making product recommendations. There will always be someone asking for help with their insecurities, and they’re will always be questions about different skincare products.

Moira: How did you transition from community building to a million-dollar business?

The big turning point was revolutionizing the influencer business model. Normally, influencers are run by these management companies who are behind the scenes. A lot of people don’t see this how there are agents and corporations telling influencers to show up specific places, to promote this product, and do XYZ. 

I encountered a situation where a manager didn’t have my best interest in mind and they only had their commission in mind. Suddenly, my job was becoming a source of stress because I had to answer to this manager who was forcing me to promote things I didn’t believe in. 

So ultimately, the real work began when I understood for myself what makes people click on content. I learned that I can captivate an audience by recommending the best products, and then following up with the message that our looks don't define us. While discussing skincare, I can tell people that what you  do for the world is more important.

However, once I realized that I could be my own boss, I soon realized that I had to be a boss to other people. Deciding to become a boss and taking hold of an organizational structure was something that no amount of school or coaching could have prepared me for.

Moira: What was the biggest challenge during this process?

Cassandra: Learning to let go of something that started out as a diary and letting it bloom into a business was very hard. This business literally started out with me sharing my bleeding face and working through my deepest insecurities. Then, all of sudden, I’m having calls with Good Morning America. How do you prepare for that, and how do you prepare a team that actually cares about helping others and has the same vision? Luckily, we have a trustworthy team that’s gone through similar things.

Moira: How have you learned to build a personal brand that can evolve but remain consistent?

Cassandra: I think trust is at the root of this. If I’m going to make a recommendation to you, you have to trust that I have your best interest in mind. I am the one who has to be okay with my actions. So, I have to focus on building something that’s not about money and followers. There’s a huge amount of responsibility that comes with supporting someone through their insecurities. We’re not not trying to fix people. Instead, we’re trying to go on a journey with them. It takes dedication and non conformity for a brand to guide people and tell them that they are enough. That trust is truly fundamental to our brand, but it’s one of the hardest things to do. 

Moira: You’re speaking to a diverse audience across many platforms now, how have you learned to adapt?

Cassandra: I was such a different person when I first started. I had a high squeaky voice, and I was in $80,000 worth of debt. I would spend money on clothes, and I wore shirts in my videos where people could see the logo. I was that insecure, and looking back I’ve changed so much. But I think it’s a great testament to how we all grow and step into who we are meant to be.

Moira: Because you are so committed to your values, How have you learned to take risks and bounce back responsibly?

I believe in failing responsibly. It’s human nature to make mistakes. We’re not defined by mistakes, but what’s impactful is how we recover and work through them. As a content creator, a lot of you failures are public unlike a businessperson who is behind a brand. You are public with your personal life. However, this is refreshing.

It gives me a sense of responsibility. If I were able to hide, I wouldn’t feel it as viscerally. My content is based off of skin journeys. As a content creator, how I live is what I create, and that makes me very accountable for the things I put out there.

However, personal responsibility isn’t always something that traditional business schools teach the best, especially in this day and age where human connection is more rare. Whether its content, a car, or a watch, people identify a lot with products.  Being personally responsible for the content our audience consumes helps me to stay grounded, especially when I’m risk-taking and tyring to advance the business. 

Moira: What does it mean to be an entrepreneur on YouTube today?

I think it’s very different from what people expect it to be. We’ve got a whole team of employees, contractors, and people who work every single day on our content. When it comes to failure, it takes a lot of strategy, innovation, and optimism. I used to look at failure as this end all be all, but now I’ve redefined it and put it on a linear scale. My perspective has changed though.  I believe that you have to fail a certain amount of times to get to success. 

Moira: How do you respond to negative feedback? Does it hurt?

Cassandra: Yes, it hurts, but if it doesn’t hurt, that means I’ve become detached. Having a team I can talk to helps, and I think the fact that we’re getting some sort of pushback means that what were doing matters. Negative reminds me of my purpose, and to see my flaws in an objective light.

Moira: What would you say to your younger self, the person just embarking on this journey?

Cassandra: I would say fail forward. Lean into those mistakes because they’re learning lessons. Learn from failure, and see how can you adapt. Also, ask for help. Asking for help is an opportunity to connect and that’s what will build a community you can celebrate with.