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The Hard Lesson StyleSeat CEO Melody McCloskey Had to Unlearn to Become a Stronger Boss

Melody McCloskey StyleSeat CEO

Melody McCloskey admits that she was “not knowledgeable about beauty and the industry” prior to co-founding StyleSeat. During her college years, she dyed her own hair at home because she couldn’t afford to get it colored at a salon. “I wanted to feel good and for [my hair] to look more professional than what I was able to do,” McCloskey says.

She also remembers feeling “really intimidated” by the arduous process of finding a stylist. “I not only wanted someone who could deal with my hair and fine texture — you can’t just do anything you want to it — but I didn’t want to have to become the world’s expert in all of the salons in San Francisco,” explains McCloskey. And because she didn’t know much beyond box dye labels and instructions, McCloskey was unable to communicate exactly what she wanted or be confident that she had discovered a colorist who could help achieve the look she desired.

“Once I started talking to stylists and salon owners, I realized that it wasn’t just me that was frustrated,” she says. “They didn’t have a great way to market themselves, attract the type of clients they want, and build their business. Really simple things like payment, scheduling, and marketing… the digital economy had left this industry behind.”

While McCloskey’s search for a stylist she could vibe with continued, she embarked on another beauty mission: to create a platform that empowered women and entrepreneurs who are artists to be successful at doing what they love and empowered consumers in what is a powerful form of self-expression.

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StyleSeat was born in 2011 when she and co-founder Dan Levine launched the online booking destination for salon professionals; it has become the premier marketplace for independent beauty Pros to grow their businesses, and where Clients can easily discover and book their beauty and grooming services.

Keep reading to find out about the hard lessons Melody McCloskey learned along the way, the people who helped to push her past her own fears, and how she hopes to be a role model for her daughter and the next generation of successful businesswomen.

What was the biggest business challenge you faced early on and how did you overcome it?

Easily my own hang-ups. I thought that I wasn’t smart enough to start this company. I didn’t have a business background. I wasn’t a software engineer. I didn’t look like any of the other people I knew who were starting companies (men) who had gone to Harvard or Stanford and were welcomed into the Silicon Valley and investment community with open arms. I constantly felt like I was so lucky to even be in the room.

A lot of things that society teaches women about being polite and nurturing, you have to unlearn and redefine in business. And I had to learn that lesson for myself because no one is going to teach you that. I had to go through some pretty terrible situations to get the courage, confidence, and fire to not care about anyone else’s opinions and the rules of business and to do what worked for me, my company, and my community. That was a very hard lesson, but I think it made me a stronger CEO and business owner today.

The StyleSeat Pro community is made up of 80 percent of women entrepreneurs. How do their journeys motivate you?

Starting this company I didn’t pay myself for the first 18 months. I was in an apartment with four or five roommates. My room was 10 feet by 10 feet. I was living off a couple hundred dollars a month and was just putting everything on credit cards. I didn’t do that because I love eating food out of a can every day or eating pizza from across the street. I was in tons of debt but I started this company.

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I would go and talk to stylists and get them on the app, get feedback. I would sit in salons all day because I didn’t have an office. But also, I’d watch how stylists worked with clients, managed the front desk, cleaned, scarfed down food in the back while their client was getting shampooed or under the dryer, and got back to working these long hours. And I really, really wanted to help these talented artists.

I’m the least creative person I know, but our community is so talented and I really wanted to help them be successful. I saw how hard they worked, the impact they had on their clients’ lives and day. I felt it myself when it was the most luxurious thing I’d treat myself to every six weeks. And I knew how that made you feel when you found the right person, and that keeps you going.

When you hear about the sacrifices people make to be in this industry. When you hear about how hard they work, how they really want to make it… I really felt there wasn’t an inability for stylists to become their successful selves. It really fed me during those times when it was really hard for me… to connect with the community and see the impact we had.

What is the best career advice you’ve ever received?

First, have a really great support system. It can be your mom. It can be your girlfriends. It can be your partner. Having a safe place… like when you’re showing up and supporting people and showing your great vision, you need to be able to come home and say, “I don’t know what I’m doing?” And you need someone on your side who doesn’t care if the company goes away but is on your side and really cares about you personally.

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Second, find a great mentor. Whatever your sector, whatever your level of business, find men or women that inspire you and support you and are going to give you that honest advice and help you navigate challenging situations. Some of the hardest, craziest business moments I’ve ever had, I got courage to do those things from my network of mentors and people I respect.

In addition to being a CEO, you’re also a wife and mother. Why is having a supportive partner and family so important, especially during difficult times?

Melinda Gates once said, “If you choose to have a partner in life, whoever you choose is probably the most important decision you make.” And I have a partner who is extremely supportive in my career and ambitions, who sees it as a huge asset, who sees me as successful, wants me to win, and wants the same things that I want.

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But the support system goes beyond your partner. I have an amazing sister, who stepped in when I needed her. I have an amazing nanny for my daughter, who allows me to take the time I need physically to work and feel confident that she’s happy, safe, learning, and nurtured when I can’t be there during those hours in the day. I also have amazing coworkers. We’ve created a culture at StyleSeat that is family-friendly and encourages people to show up as their whole selves. If you need to take the time to be a parent or be there for a family member, absolutely do that. We have a flexible schedule and that’s always been important for me and I think is important for others.

We have to remember that we are not just workers at a company. We are humans with human relationships. When your coworkers embrace that, celebrate it, and not just tolerate it, it allows women (where unfortunately the household burden still falls predominantly on) to be productive team members at a company. That’s exactly what we want. I try to create a culture starting with me and my management team. That’s totally normal for me even though it’s not for others. But I think it’s a function of having more women leaders to have a more balanced work culture.

Who are the women in your life that push you to be better?

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The woman who had the biggest impact on my life would be my mom. She was a stay-at-home mom when I was growing up and she sacrificed a lot for our family. I am thankful for that and also thankful that she encouraged me — whether that was to have a career, stay at home, something in between, or all of it. She encouraged me to just be full. This may sound silly, but she wasn’t telling me to go get married and have kids when I was in my 20s and 30s. She wanted me to be happy and to do what made me happy, and I’m thankful for that. I think that’s one of the reasons why I had the confidence to pursue the things that made me happy.

What lessons about being a boss do you want to teach your daughter?

I want her to see that her mom cares for her, loves her, and is also doing what makes her happy. I get tremendous growth and fulfillment by running my company. By learning and growing every day, this makes me a better person and a better mom. I want her to know that there’s no perfect balance and that there’s no sort of perfect situation, but we all support each other. Her dad is also an entrepreneur, so there’s a lot of that energy in the family.

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I want her to be happy and excited for me and know that she’s my first priority, but I’m also a priority and that’s normal. When she’s older, I want her to find that in a relationship and to value herself. I want her to find that thing that drives her and find the confidence to pursue that. It feels natural for us, but that wasn’t the case for most women throughout history. I want it to feel really natural for her.

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