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Kerry O’Brien: “Ask for help”

I’ve found that people are very willing to help you, if you ask them. I didn’t have a manufacturing partner when I started my company. I was in a meeting with someone who didn’t have the ability to produce what I was envisioning, but I asked them if they knew anyone who could. That simple […]

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I’ve found that people are very willing to help you, if you ask them. I didn’t have a manufacturing partner when I started my company. I was in a meeting with someone who didn’t have the ability to produce what I was envisioning, but I asked them if they knew anyone who could. That simple question has opened so many doors for me and Commando.


As a part of our series about women who are shaking things up in their industry, I had the pleasure of interviewing Kerry O’Brien.

Commando founder, designer, and CEO Kerry O’Brien is the face of Commando and the embodiment of a female entrepreneur. Having no formal design background, her unique approach to the fashion industry has broken boundaries and revolutionized an industry. In 2012, Kerry was inducted into the CFDA, and Commando currently holds patents for innovative design in hosiery and slips.


Can you tell us a bit about your “backstory”? What led you to this particular career path?

I had a very unusual path to fashion. I started my career in financial public relations, becoming a Senior Vice president of the world’s largest PR firm at a very young age. But the day after September 11th, I quit my job. I didn’t have a plan, I just knew that I needed a change. I always say that crisis brings about metamorphosis — that was true then and it’s true now. While I didn’t start my company immediately, that step was the very first in what would lead me to founding Commando.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

Since the very beginning, Commando has been about breaking the rules. We launched a line of underwear that was about working with a woman’s body rather than changing it, right when the market was all about push-up bras and industrial-strength shapewear. And we didn’t do things the way they had been done, we did things the way we thought they should be done. We source luxury-technical fabrics, many of which have some of the world’s highest sustainability certifications. Then we cut and sew the vast majority of our product here in the United States. And we’ve been practicing thoughtful sourcing since the beginning. We’re also expanding our own in-house production operation when most companies have totally off-shored manufacturing. We fit every single style on real bodies — including mine. Fitting and patternmaking aren’t outsourced at Commando. Beyond that, I lead a company with an almost entirely female workforce. We don’t deliberately seek to disrupt, it just happens that we do things differently than most other brands in our industry. And I think that’s been to our great advantage.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Early on, I didn’t think I had permission to venture out of intimate apparel. That might not seem funny, but to anyone who knows me it’s shocking and kind of hilarious, because I never let anyone tell me what I can and cannot do! Once I realized that I didn’t need permission, Commando was unleashed. Now we have an amazing loungewear and ready-to-wear business, in addition to our intimate apparel line.

We all need a little help along the journey. Who have been some of your mentors? Can you share a story about how they made an impact?

Josie Natori was unquestionably a mentor. I was a young upstart breaking into an established industry where many of my competitors were heritage brands with long histories. When I met Josie, at an airport lounge on our way to a tradeshow in Paris, she immediately welcomed me and invited me to a gathering at her beautiful Parisian home. She is that rare human that isn’t threatened by the success of others. She truly believes that a rising tide lifts all ships and I think she was excited about what Commando was doing for intimate apparel.

In today’s parlance, being disruptive is usually a positive adjective. But is disrupting always good? When do we say the converse, that a system or structure has ‘withstood the test of time’? Can you articulate to our readers when disrupting an industry is positive, and when disrupting an industry is ‘not so positive’? Can you share some examples of what you mean?

Disruption is positive when it brings about needed change. In the example of intimate apparel, when Commando launched, no one was talking about comfort. Because why would a woman need to be comfortable? It was all about making her body confirm to an ideal that wasn’t all that ideal. So, I am proud to say that Commando contributed to positive change. Obviously, we are all currently experiencing negative disruption via the current global pandemic. But I really believe in humanity’s resilience and adaptability, and I think some good could come out of this in the end. It’s forced a lot of reflection in the fashion industry around waste and excess, and I think that is unquestionably a good thing.

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

What about the three maxims that guide me every day? They aren’t pieces of advice, but things I have learned along the way. They are:

  1. Ask questions. When I started I asked questions that some people might have been afraid to ask about how garments were constructed or the way things were done. This is where my outsider’s perspective was enormously useful. Why is it done that way? Why can’t we do it another way? These are things I ask all the time.Asking questions is a sign of strength, not weakness.
  2. Ask for help. I’ve found that people are very willing to help you, if you ask them. I didn’t have a manufacturing partner when I started my company. I was in a meeting with someone who didn’t have the ability to produce what I was envisioning, but I asked them if they knew anyone who could. That simple question has opened so many doors for me and Commando.
  3. Ask for more. I say this more than anything else and I love by these words. Never be afraid to ask for more. From yourself, your team, your company, your industry. No one is going to hand you anything. You have to ask for it.

We are sure you aren’t done. How are you going to shake things up next?

I love change and I love evolution, and I never put any parameters around what comes next for me or my brand. But you are 100% right — I am far from done! I can’t say what’s next, and that’s the exciting part!

In your opinion, what are the biggest challenges faced by ‘women disruptors’ that aren’t typically faced by their male counterparts?

It can be hard to be a female leader. I think women second guess themselves more. I think about how I let others define me in the beginning. That is outrageous! I’m now unapologetic about our ambition potential, and ability to make life-changing clothes.

Do you have a book/podcast/talk that’s had a deep impact on your thinking? Can you share a story with us?

I was lucky enough to be included in Hillary Kerr’s SECOND LIFE podcast and am a huge fan. She features female founders and entrepreneurs, and the podcast itself is focused on reinvention — one of my favorite topics! Hilary is great and conversational and fun, and she gives you a real sense of how circuitous success can be.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I’ve always thought that true self-confidence can be a remedy to so much. If we could instill this to all men and women, many things would change for the better. People would be better at advocating for themselves and using their voice.And I truly believe in using your voice! We have recently partnered with HeadCount to help drive voter registration and turnout. I think right now, one of the most important things we can all do it participate in our democracy.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I don’t live by anyone’s life lessons… except my own! One more “Kerry-ism” is, “When in doubt, check it out.” Because anytime I’ve said yes to an opportunity, I’ve either gotten an idea, made a connection, or been encouraged to think in a different way. I appreciate that now more than ever.

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