10 Questions with StyleSeat Founder Melody McCloskey

  • By: joannafurlong
  • Posted: March 30, 2017

There’s no holding her back. Melody McCloskey, founder and CEO of StyleSeat, is happy to candidly share unfiltered details about where she’s been and where she’s going. She offers the unique perspective of a startup founder in the eye of the storm: she’s no longer doing it ALL herself—she has a great team behind her—but she’s on a continual growth journey. She shared her wisdom with Girls in Tech, including why she starts her day by NOT checking her email.

See her live. Melody is speaking at Girls in Tech Catalyst Conference in San Francisco, June 20-22, along with more than 50 other speakers from all corners of tech. You should be there.

Melody McCloskey, founder and CEO of StyleSeat

Melody McCloskey, founder and CEO of StyleSeat, center. She’ll be speaking at Girls in Tech Catalyst Conference, June 20-22 in San Francisco.

What was the single hardest thing for you in the early days of StyleSeat?

Just having the confidence to know that I could do it. I had had the idea for two years—I was obsessed with it. I wanted to be a founder, but every time I got excited, I would think to myself, “You can’t. You can’t fundraise. You’re not smart enough,” and so on. But I got over it, and it was a slow thing, it took a lot of time. . . I think a lot of women do this. They can be overthinkers. The biggest thing for me was just to do it. I realized that even if I fail, I’ll still be happy. And even today, I try to be less hard on myself. The expectations I set for myself are unattainable. Every day I try to cut myself a break.

You’ve spoken a lot about the struggles with fundraising. What parts of it has gotten easier over time, and what’s stayed the same?

In the beginning, I raised money from family and friends. I pitched them, and I had to convince them that I was the right person. Then, with Series A round, it was all about showing the app, and what we’ve done so far. For the Series B round, it became all about the numbers and less and less about me and the personality. As you grow and continue to fundraise, it becomes less about you as a founder.

How did you get the message through to investors about the potential of StyleSeat?

I was in a pitch meeting. I was telling the guys in the room that women spend, on average, about $3,000 a year on beauty. They were skeptical and I told them, that’s the whole point of beauty. You spend a lot of time on it, a lot of money, and it looks like you’ve gotten nothing done. They didn’t get it. One of the guys in the room said his wife did not spend anywhere near that amount. I told him, “Yes, she does. I know for a fact she spends $1,500 a month on her cut and color alone.” I had done the work before the meeting, I knew who his wife went to for her hair. His jaw hit the floor.

And then there was the time I presented to 14 men. They didn’t believe me that this was a big market. So I asked them, “Who here has a wife who is blonde?” They all raised their hands. I told them that none of their wives’ hair was natural, not after the age of 20. I made it personal to them, and drove home the fact that their wives were spending a tremendous amount on beauty.

How do you start your day to set it up for success?

I’m a huge morning person. I have more trouble getting to sleep. But I typically wake up about at 5:30 or 6:00 and I’m usually at the gym by 7. I work out with a trainer or I take a class. When I come home, I have a protein shake. I like to play music to tune out. I go out of my way to not check my email or phone. I like to let my subconscious process. I may even clean and do things like that in the morning—I like getting things done. But I purposely avoid turning on my brain just yet. If I let my brain operate in the background, I always find answers.

What’s been a major defining moment for you in life, and how?

I used to doubt my decisions by a million percent. I’ve learned confidence now, and I’ve learned to trust the decisions that I make and the things that I do. Now, I consult with my team and with my Board, but I may not always take all the advice. Now, the decisions I make are often the right ones.

Who are the key influencers in your own life?

My parents for sure. They are very driven, moral people. Very considerate and thoughtful. And my fiancé. He and I are opposites. He cares deeply about me, but he approaches problems very differently.

What’s your secret to prioritizing work and getting a lot done?

I’ve had to change my approach to how I work every two weeks. Now, we’ve built up an executive team. I meet every week with my EA. We identify the top three challenges the company is facing. Everything else on my plate, I fit in, but those are the three things I tackle each week. These are the three things that I can most help with, whereas I trust my executives to execute.

What are your favorite business books?

I use audio books; I listen to one to two books a week, a combination of business and non-business books. I listen to books when I’m commuting, when I’m cooking. I don’t watch a lot of TV. I loved Grit: The Power of Passion and Perseverance;  I also really liked Amy Poehler’s book, it was pretty deep.

What’s the best and worst advice you’ve ever received?

Worst advice: You need to seek out the fanciest people and work with them. Well, working at big corporations is a lot different than a startup and not necessarily a great fit. Best advice: Find people who love to solve hard problems. Not everyone likes to do it. Work with people you really love and trust and who are effective. If you really love the people you work with, you can be very effective, even give each other shit and have fun.

You’ve raised a lot of money and your team is growing a lot – how do you stay on top of the change and keep up your team’s spirit?

It’s all about the ability to adapt. When you first start out, you’re an evangelist. And you need to hire a team of generalists and just get stuff done. But then as you grow, you need to hire more and more. You transition to a more critical role. Now we’re at the point where we have operations and my job is more about culture and looking to the future. I try to make sure everyone is happy and taken care of.

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