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Interview: Britney Winters of Upgrade Boutique

Interview: Britney Winters of Upgrade Boutique

Britney Winters of Upgrade Boutique featured on top Seattle career blogger, Whit Wanders

Welcome to my Interview Series where I feature amazing female entrepreneurs & digital influencers that are breaking ground in their space. This week I am featuring Britney Winters founder of the Upgrade Boutique!

I am excited to introduce a new Female Founder and Black Owned Business. My latest interview is with Britney Winters CEO and Founder of the Upgrade Boutique in Houston, Texas.


Britney Winters is a Black business owner and has raised more than $300k from Venture Capitalist firms to start her own hair salon and hair extension company in Houston, Texas.


Britney is a graduate of Stanford University.  She moved to New York to work on Wall Street as an analyst with Credit Suisse.  In addition, she's a graduate of Harvard Business School and has a wealth of knowledge when it comes to fundraising for your business.


Her Houston based salon, Upgrade Boutique, which uses human hair extensions to make custom wigs, has really made an impact with its customer with over 24 thousand Instagram followers: @TheUpgradeBoutique.


When Covid-19 hit Britney had to pivot her brand and the salon services to 100% online. She is sharing her story about transition her service-based brand online and advice for those looking to start their own business and raise VC funding.


Scroll down to read the Interview:

 Thank You to Britney for taking the time to answer all my questions. 




What was your main starting point for launching your own company, Upgrade Boutique?

When I was a student at Harvard Business School, there wasn't a lot of very skilled stylist who were good at working with Black hair, at least I couldn't find a lot of good stylists in the area. And I know a lot of the other students of Black female students were having the same issue. So a group of us would take a bus trip to New York City for the day just to get our hair done. And I thought it was like the most ridiculous thing ever. It was expensive and it took forever. I realized in this problem lay a huge opportunity and untapped market.


What is the mission behind Upgrade Boutique and why has it been such a success?

I've been wearing hair extensions consistently since I was about 16 or 17 years old. It's become a lot more important for us [ Black women] to embrace our natural hair in its natural state. My hair in its natural state is not straight, it's very tightly curled and I love my hair but it does take a lot of time to style.


I remember when I was just starting out my career and I had a job on Wall Street and I had a mentor who was a female, a white woman. I think she was coming from a very genuine place but I remember I came to work with braids once and she was like, 'I don't think you should do that because I'm concerned about how you might be perceived.  I think that moment increased my dependency on extensions.


All of those experiences really made me want to deliver this service in a different way. That made it a lot more convenient and accessible for women so they can spend more time and money on doing things that they love.


Tell us about the Upgrade Boutique and services & the impact of COVID-19?

Before Covid-19 we operated as a traditional hair salon but with Covid-19 we had to be creative and rethink our business model. We really started to emphasize more online services, which we had always offered. We supply the product, which is the wig, and then we work with our network of stylists. Our stylists work behind the scenes to color the wig and customize it to make the hairline look natural.


Our customers are able to submit pictures of looks that they want to replicate and then the colorists and stylists work together to create those looks. Then we ship it to the customer. So we make ready-to-wear wigs and extensions. There is this whole technological process in the background that enables us to coordinate these services because a lot of our colorists and stylists are not actually based in Houston, Texas.



How has your business had to shift and pivot in the wake of COVID-19?

We had to completely shut down and close the salon, it really made us kind of change our marketing and really emphasize online angle. It's almost completely reversed operating model and the majority of our clients are utilizing e-commerce features across our site. Now during Covid-19, things look a bit different. The stylists now work from home and create different colors, create different styles that are completely custom for each customer.


With Covid-19 the entire shift to online and building the delivery and supply chain for the business. Being able to work with my network of stylists and responding to the customer in a timely manner to be able to get them what they need. We're always looking for ways to improve our supply chain and cut down on delivery times. We are always seeking to increase or to improve our customer experience. Right now, we're working with tech consultants to see how we can even further enhance our Web site and cut down on delivery times. So really kind of coordinating the logistics and the technology behind the scenes that enables us to offer a faster and better service to the customer.


You were able to raise $300,000 in VC funding for your company - What are your tips for women looking to become investors in startups or women-founded businesses?

Make sure you know and understand your Value Proposition so you can translate it to your customers and VC. You also need to Prove Out Your concept to ensure you have the numbers and market to make your case. In my case, we did pop-up shops, and in the first pop-up shop we sold out in three hours because people just couldn't believe the value proposition that we were offering: we're gonna have you in and out within two hours.


Being able to bring that data to the table when we're talking to VC is very powerful. It's no longer just an idea. It's an idea that I've tested and I can prove to you that there is a demand for this. I definitely think that that's the angle a lot of women and, especially, minority entrepreneurs, we have to go that route to get the appropriate attention and investment.


Do you feel like you had to navigate the VC world differently as a Black woman? What advice do you have for BIPOC founders?

Use your rejections and the no's to level up your pitch and your deck. I also worked very diligently on our pitch deck, kind of seeking to understand what good pitch decks looked like, talking to anybody. But you also have to withstand rejection. I got 100's of "no" on my initial pitches. But each time and I got rejected, I would take something away from that conversation that I could either embed in the deck in itself or into my pitch.


It grew to become something I was very proud of and that I could defend. And I knew that I could answer almost any question that somebody would throw at me. So that's also my advice to entrepreneurs, is to not become discouraged. You know, when you get these rejections is just part of the process.


What business advice do you have for women looking to build their own brands or companies?

Hire people who have similar values as you do! I want to work with people that have integrity, that are organized and have similar goals. We're recruiting new stylists and colorists onto our platform all the time. We spend a lot of time vetting our stylist because at the end of the day, we owe it to our customers to deliver what we say that we're gonna deliver. We want to work with people where if the customer is not satisfied, you know, they're going to do whatever it takes to make it right.


Our stylists are an extension of our brand and service and we want to ensure from end-to-end we are getting the client what they want - which is their hair. I've had to also learn to let go and give up the reins of some parts of the business. We brought our staff in because they have different skill sets, different things to bring to the table and you have to trust them.  You have to really let people have ownership over their area. And so that has really freed up a lot of my time to focus on the more value-added activities.

How have you used Social Media to help build your brand in the digital space?

We've really used social media as a great tool to reach our customers. And now, with everything being shut down, it's the easiest way to reach your customer because people don't have anything else to do but scroll on all day long and they are constantly looking. We've had a few of our wig installations go viral. One of our stylists, Carter (@king_carter90), styled a wig for Savannah James, who's LeBron James is wife.


We've also changed our social media messaging because previously we would kind of emphasize the stylists installing a wig on a client. So most of the content that we were producing was in the salon and it was showcasing that end result of a client having a wig installed. Now, it's more so about the wig itself and not the installation. We've also reached out to customers that we've shipped wigs to. We asked them to send us content to be able to feature them across our social media.


Do you ever experience imposter syndrome? How do you deal with it?

Oh gosh yes! Imposter syndrome. I feel like has been following me since I made it to Stanford. I think actually now, though, because I've been through so many different experiences. I'm a lot more comfortable in my own skin. My dad used to always tell me that I would struggle with this like a lot. Like, why did they pick me? Why am I here? And my dad would always tell me, you are not their token. You're there because you earned the right to be there. And I think after all these years, I finally have come to a place where I believe that.


After leaving Stanford and go to Wall Street, where there are very few people that look like me, went on to Shell, which is still, you know, oil and gas, a very white male-dominated industry. After having those experiences and not only, working in those environments, but thriving. It helped me to believe in myself and to know that I do have value anchoring something to the table. And it's not just my skin in color.


I bring diversity because I am a black woman. But I also bring creativity. I bring intelligence. I'm very grateful that I had those experiences because it is tough being an entrepreneur, and you'll face different challenges. But everything I went through has helped prepare me for what I am now.


Any time management tips for juggling your career and your personal life?

So I always keep this running list of, like, are our goals. And these are big, audacious goals that, you know, they don't really change. Then I have to distill down those goals. OK, what is it going to take for me to achieve, X  or Y. I try to move the needle every day, every week. So I'll break those goals down and structure my day around the things that relate to us achieving those goals.

And so if you plan to prioritize effectively, you can kind of I mean, urgent things will always come up there, always be there. But if you're spending a significant amount of time planning, you know what's to come and the direction you want to go in, you know, ideally you should be spending more of your time on tasks that are important versus urgent. I'm one of those people that keep lists of everything that needs to be done by the day. It gives me a lot of satisfaction to cross things off my list,


What is in store for you and your businesses for the rest of 2020 & moving into 2021

I would like to return capital to our investors and continue to grow and be profitable. And then I have a unique place in my heart for the stylist that we work with. So I have some very stylists, specific goals. I've learned so much just about the industry and a lot of the stylists work as independent contractors and a lot of stylists like don't even have access to healthcare, 401K, etc. I would love to build out and give them the tools to be successful. A lot of stylists, they deal in cash and then they've worked hard all these years and then they get to the end and they do not have those foundational elements you have in Corporate America. Helping stylist become better entrepreneurs, how to take it beyond just the craft, but also focus more on the business aspects of it, the professionalism and the soft skills.


CALLING ALL STYLIST: If you are a stylists and interested in working with the Upgrade Boutique. Please email:


Follow the Upgrade Boutique on Instagram!



If you are new here - make sure to check out my Work Series where I share personal stories, interviews, and career lessons to empower women in the workplace.

Know any amazing female entrepreneurs or boss ladies?

Email me and tell me who you think I should interview next!



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