Meet the Harvard Business School Grad Elevating Your Wig-Shopping Experience

Britney Winters

Britney Winters

The Hustle

Welcome to Byrdie's new series, The Hustle. We're profiling BIPOC women and woman-aligned folks in the beauty and wellness industries who are usually behind-the-scenes. From the cosmetic chemists formulating your holy-grail serum to CFOs driving the biggest beauty companies forward, these women are the definition of career goals, and they're getting real about the journeys that led them to where they are—the highs, the lows, and everything in between.

The global wig and extensions market is valued at 5.6 billion and is expected to reach 13.3 billion by 2026, according to a report published by Arizton. While the industry is booming, the wig and extension shopping experience has been far from seamless for the everyday consumer. When it comes to wigs particularly, you often have to navigate a multi-step process (from finding a quality hair vendor to tracking down the right stylist to install the wig) to achieve your desired look. As someone who has been wearing protective styles since her teens, Britney Winters grew frustrated with this process and saw an opportunity to create a solution.

In 2019, the Harvard Business School graduate launched Upgrade, a marketplace offering high-quality, customized wigs and hair products, and has been working to elevate the wig buying process ever since. Ahead, Winters opens up about the highs and lows of her entrepreneurial journey, opening a brick and mortar location in Houston, and her advice for other beauty founders. 

You've worked at places like Shell and Accenture. Tell me more about what you were doing before launching Upgrade Boutique.

I went to Stanford for undergrad and majored in engineering. However, I've never worked as an engineer. My first job was as an analyst at Credit Suisse on Wall Street. I did that for a few years and then moved back to Houston because I got custody of my sister. 

I then took a job as a management consultant. And then later, I got staffed on a project doing consulting for Shell Oil Company. And then that resulted in a full-time offer. They sponsored my MBA at Harvard Business School. So, I took a leave of absence to attend business school. And while I was in school, I conceived the business plan for Upgrade. I didn't act on it at the time because I needed to go back to Shell and fulfill my commitment to them since they sponsored by MBA. I went back for three years, but I was feeling unfulfilled and wanted to follow my passion. And so, after the third year, I decided to leave and focus on Upgrade full-time.

What inspired you to launch Upgrade Boutique?

I have been wearing hair extensions since I was about 16 years old. And initially, it started as something I did for fun, but over time, I think I kind of got addicted to it. I didn't like the way I looked without extensions. While I was in business school, I was going through a self-reflection and self-love journey. And at that time, I began wearing my extensions more so for convenience. But while I was in Boston, it was challenging to find stylists specializing in extensions.

A few of the other Black female students and I started coordinating day trips to New York City to get our hair done. Meanwhile, I was still a full-time guardian to my sister. So, I was trying to juggle school, being a parental figure, and taking these trips to get my hair done. I thought there had to be a better way of doing this. At Harvard, I was in a class focused on innovation. For my project, I wrote a paper on Drybar, and I saw a lot of things that they had done to the blowout industry, and I felt like there were a lot of similarities around what I wanted to do. I just started doing more and more research. During my second year in business school, I took a class on entrepreneurship and made Upgrade the focal point of my project. I later participated in the school's pitch competition. I did not win, but I got positive feedback from the judges. So, I felt like I was onto something.

How does the Upgrade experience work?

When you want to get a wig made, there are just all these steps in the process. You have to find a hair vendor, purchase the hair, take the hair to the stylist, wait for the stylist to create the wig, and then you usually have it installed by the stylist. I wanted to create a marketplace that would allow women to skip the salon or reduce their time in the salon. We've created a marketplace that allows women to submit pictures of their hair inspiration and select a stylist to recreate that look. 

One of the issues I've personally experienced is hiring stylists to create wigs, and then once you get it, it's nothing like what you envisioned. Our technology helps to ensure that you're getting what you want. The stylists have to submit a picture for your review and approval before it's even shipped to you. If you don't like it, you get to provide feedback, and stylists will make tweaks. Once the stylist creates it and you approve it, it's shipped to you and arrives ready to wear. You don't even have to visit the salon.

Britney Winters

Britney Winters/Byrdie

What has the experience been like building Upgrade Boutique? What have been some of the challenges you've experienced? 

The first challenge was funding. I did pitch to many different VCs initially and heard "no" many times. I think it's unfortunate most people making those decisions are probably not familiar with the pain points. I had to go back to the drawing board and provide a lot of context and education within my pitch to make them understand that this is a huge market. Eventually, I found the right partners, and I think that's when the real challenges begin because you have to build out a team. 

When I started, I was doing everything myself. I was posting on social media, doing order fulfillment, and accounting. Now we've grown to a point where we have people in those roles, so it's more so my job to support them and make sure they understand the vision. It's been a blessing to hire specialized people that can focus on different divisions within the company.

Another challenge is that it is a very competitive market, and you have to figure out how to stand out. I think we've done a really good job by focusing on the luxury, tech-enabled experience we provide. 

At the end of this month, you’ll be launching a brick-and-mortar retail and service location in Houston. Tell me more about it. 

I'm really excited about that. There is a transition going on in the industry where many stylists are moving away from open-concept, full-service salons. They want to feel empowered to be their own business owners, and many of them are migrating to salon suites. I think salon suites are great because you get that private setting with your stylist. But then there's a piece that's kind of missing because, in the past, we would go to the salon to socialize with other women. We're offering the best of both worlds because we have private salon suites, but the space also has a huge wig bar and lounge area to help our clients build a sense of community.

We wanted to create a space for women of color focused on accessible luxury. We spend a lot of money on hair care, and we often don't get an experience commensurate with the amount of time and money being spent. Whenever our client walks through our door, I want them to feel like they're being pampered.

What has been the most rewarding part of building Upgrade Boutique?

Getting positive feedback from customers has been the most rewarding part. Even on the most challenging days, it gives me the strength to keep going. We're making women happy and helping them feel more beautiful. That's important to me because when you feel good about the way you look, it just permeates through other areas of your life. You show up more confident. I've personally experienced it, and I want every woman to feel that way.

We're making women happy and helping them feel more beautiful.

What advice or words of encouragement do you have for anyone looking to start a beauty brand?

You have to be completely focused and dedicated. Some people might assume I may have had it easier than other people because of my background, but that's certainly not the case. I was the one reaching out to stylists trying to convince them to partner with me when all I had was an idea. So, you have to be relentless. Even when you might feel discouraged, you have to stay focused and positive. I know it sounds cliche, but that's what kept me going.

What does beauty mean to you?

It means confidence. I always feel like I do my best when I'm feeling beautiful and that is very tied to how I'm feeling about myself. When you show up feeling like your personal best, it positively impacts so many other things in life.

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