We’re excited to introduce you to the always interesting and insightful Tianna Cunningham. We hope you’ll enjoy our conversation with Tianna below.

Hi Tianna, thanks for joining us today. Can you talk to us about a risk you’ve taken – walk us through the story?

Nine months ago I made one of the biggest decisions of my life today.

I wasn’t sure what this decision would hold for my future, but in that moment I didn’t care because I knew I was following my purpose.

In May of 2025, I walked away from my 9 to 5 to follow my passion as a full time entrepreneur.

For the past three years, after graduating college with a degree in fashion merchandising, I thought I had my life figured out. My plan was to become a visual or retail manager, and in about two years I would land a corporate job in fashion. I started my career as an assistant manager making a decent living for myself. I stayed this course to eventually work my way up into the fashion corporate world. Before reality hit, two and a half years had gone by and I wasn’t seeing as much growth in my career. I found myself having to leave multiple jobs due to unhealthy work environments, being mistreated, overworked, and not taken seriously as a young Black woman in a leadership position.

I became depressed and desperate for a change in my career. After continuously searching for a new job, nothing was speaking to me. I didn’t want to go into another retail job that would be another disappointment. I decided to put my happiness first even if I didn’t know what came next.

I knew it was my time to walk away when things were no longer coming into alignment. The plan I had for myself is not the plan that the universe has set for me. When I came to this realization I knew I had to follow my passion which was becoming my own boss. I needed to pave my own way which was getting back to my makeup and clothing line.

What started as a creative outlet turned into something much deeper. I wasn’t just playing with makeup I was building something that felt like mine. Not placing my entire career in the hands of people who don’t have my best interest at heart. I’ve always loved fashion and beauty- not just the glam, but the transformation. The confidence shift from the moment a client looks in the mirror and sees a new version of themselves.

That same month I quit my job, I found a shop in my neighborhood where I rented out a booth to start taking clients. The next month I found myself getting booked every week whether it was two clients or six, I was proud to know that people saw my talent and genuinely wanted to support me. Since then, I’ve built a clientele of amazing women, collaborated with some very talented business owners creating ad campaigns, photoshoots, and hosting events. I celebrated my 4 year anniversary for Misfit Makeover in November 2025 and have continued to push and progress.

Being a full time entrepreneur is not always easy the way it seems on social media. You have to have discipline, self motivation, and patience. Every no that I’ve been told, every slow season, every delay is a lesson turned into another blessing. No matter what I still keep going. I am constantly investing into my business and reinventing ways to improve.

Nine months later I can say this, it was the best risk I’ve ever taken and I would do it all over again!

Tianna, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

For those who haven’t read or heard about me before, my name is Tianna Cunningham and I am a 26 year old entrepreneur, makeup artist, model, creative director, and fashion lover!

Born and raised in Maryland, most of my fashion taste and creativity comes from my environments. My personal style plays on edgy streetwear with a sexy girly twist. Since the age of 6, I knew I would have a career in the fashion and beauty industry. While other girls my age were watching cartoons, I was in my room watching “Project Runway” and “America’s Next Top Model.”

I studied cosmetology in high school where I developed my love for the beauty industry, specifically in makeup. In cosmetology class, we would watch YouTube tutorials with famous YouTubers like Aaliyah Jay and Princess Rese doing different makeup looks. I started to bring my own makeup to class and did my face everyday which turned into some of my classmates asking for me to do their makeup.

My journey as an entrepreneur started in college of 2018. One of my fashion class projects was to create a power point of a fashion boutique with our own clothing line. The name Modern Misfit came to me so naturally. The meaning behind the name wasn’t just about a brand, it was a mindset. “Modern” acknowledges that we live in a time where individuality is the new currency- not just in fashion but in our society. To be a “misfit” is to be someone who doesn’t conform into boxes that society tries to force them into. I wanted my brand to be a statement.

In 2020, during the pandemic, I decided to take a break from college. This time off allowed me to fully tap into my creativity as an entrepreneur. I learned how to sew and started selling custom masks which blew up, getting multiple inquiries everyday. I wanted to make Modern Misfit official. So I did my research and trademarked the name. I dropped my first product which was stacked pants. I hand sewn different pairs of sweatpants and jeans together that I bought from the thrift store and sold them online. Every pair sold as soon as I posted them. I started taking custom orders, and during the process I planned my very first collection of women’s sweatsuits. My inspiration was vintage Juicy Couture. I found a vendor in China, ordered 20 sets of sweatpants and jackets with the money I received from the state during the time of everything being shut down. I created a custom rhinestone logo design and went to work with my sewing machine. Once my product was finished I uploaded one post on Instagram and my DM’s went crazy. I knew I had to come right with this drop so I hit up my homegirl to do a photoshoot with me for the drop and it was a hit. I sold out of my first collection after doing pop ups, and selling it on my website.

Fast forward to Fall 2021… I decided to go back to school that fall semester. I took a break from Modern Misfit and decided to take another route in my second love which was makeup. At the time, I was working two jobs while being a full time undergrad student and I wanted extra money in my pockets. There was only one other makeup artist on campus so I knew I could make some extra money. With my next check I received from both jobs I bought a makeup kit, a ring light, and created a logo design. I wanted my business names to play off of each other so I came up with “Misfit Makeover.” I made a post that I was taking clients and before I knew it, I was fully booked for every school event. I perfected my craft by practicing on my friends. I got asked to be the official makeup artist for school fashion shows, modeling teams, and homecoming events. My services expanded from soft glams to full glam and editorial makeup services.

Following my makeup journey, I’ve done the Baltimore Met Gala, in 2025 I became the BMG Glam Manager, worked with Lana Rae in photoshoots for the Misa Hylton Fashion Academy, collaborated with many creatives in the DMV and done numerous fashion shows and events. What got me into those doors was my confidence and consistency. I took every opportunity that I saw no matter if I didn’t have the experience- all they could tell me was no. Most of those chances I took became yes’s and brought me into even greater opportunities. The most important things I’ve learned from being in those rooms is networking is key, first impression is everything, and be yourself! Don’t hide in the shadows make yourself known through your talent.

What sets me and my brands apart from the others is the standard I set through my businesses. I create a statement and empowerment through my work. I create my designs and makeup looks to bring confidence and self empowerment to every client. I always find ways to give back to my community whether that’s offering free makeup services to young women and mother’s in need, creating a safe space where women can express themselves judgement free while being pampered, also empowering the youth to set the standard and not conform to a system that was designed for them to fail. Speaking life and encouragement to my clients and those who support me is my main priority. It is not always about the money when you are doing something that brings you and other’s joy.

I want people to know that it is not always about what people can do for you, but what can you do for them. How can you make a positive impact through your service? That is one thing I am most proud of with myself and the community I’ve created within my business.

What’s been the best source of new clients for you?

The best source of new clients for me as a full-time makeup artist has been a strong, visually appealing portfolio supported by a strategic marketing approach.

In an industry where visuals is the focus, your work speaks before you do. I invest my time outside of doing makeup to curate my profile. I focus on showcasing a range of looks—bridal, soft glam, editorial, natural skin-focused makeup—while maintaining a consistent aesthetic so potential clients immediately understand my style and skill level. Professional photos, clean lighting, and close-up skin shots help communicate technique, detail, and versatility.

I’m intentional about how I curate my social media feeds, website galleries, and before-and-after transformations. Everything is branded consistently—from color tones to captions—so my work feels polished and recognizable. That visual consistency builds credibility and trust.

My marketing strategy supports the portfolio. I use social media not just to post photos, but to educate, engage, and position myself as an expert. Behind-the-scenes content, client testimonials, reels of the makeup process, and clear calls to action all help convert viewers into inquiries. I also keep up with my bio, booking links, and highlights so it’s easy for potential clients to take the next step.

In addition, I collaborate with photographers, hairstylists, and content creators to create fresh, high-quality content that elevates my brand. Those collaborations expand my reach to more creatives and new clients while keeping my portfolio current and dynamic.

Ultimately, an appealing portfolio draws people in, and a strong marketing strategy turns that attention into consistent bookings.

Can you tell us about a time you’ve had to pivot?

One of the biggest pivots I’ve had to make in my business has been in response to today’s economy.

With the steady rise in product costs, shipping fees, and overall inflation, being a full time entrepreneur is definitely pressuring. High-quality, professional makeup products have significantly increased in price, and as a makeup artist, we also deal with higher costs for disposables, sanitation supplies, travel, and studio expenses.

Unfortunately I have the make the hard decision to pass those financial increases fully on to my clients, or find a way to adapt while keeping my services accessible and affordable.

I chose to pivot by slightly raising my service costs but keeping the prices at a very affordable rate rather than significantly raising my rates. I became more disciplined about inventory management, purchasing multi-use products, building strong relationships with beauty suppliers, and refining my kit to focus on products that create longevity.

Most importantly, I made a conscious decision by keeping my pricing and services affordable. I understand that many clients are also feeling the strain of rising costs in their daily lives. Getting a makeup service is a part of important life moments—weddings, graduations, photoshoots, birthdays, etc.—and I don’t want pricing to be a barrier during those special moments.

That pivot required me to think more strategically about budgeting, efficiency, and value, but it strengthened my business. It reinforced my brand as accessible, client-focused, and adaptable—while still maintaining the quality and professionalism my clients expect.

Contact Info:

• Website: https://misfitmakeover.square.site
• Instagram: https://www.instagram.com/misfitmakeover?igsh=MXMxMWx4azIwYjQ2eQ==
• Facebook: https://www.facebook.com/profile.php?id=61577385805456
• Linkedin: https://www.linkedin.com/in/tianna-cunningham-a24519224?utm_source=share_via&utm_content=profile&utm_medium=member_ios
• Other: https://www.tiktok.com/@fashiongirltee?_r=1&_t=ZT-94EZHWyYTk5

Image Credits

Photographers: @danbeas_819_ & @moorenfocus

Brand Shoot: @bareskincos_

Models: @britt_jazzy_booze & @_sabrinaxx & @fashiongirltee