Ellie Mae Waters and Jeremy Wood-Ross on Building a Fashion Brand

By Selena Romero

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[vc_row][vc_column][vc_column_text]Power Couple is a new series that focuses on Canada’s most enterprising couples. This edition features the faces behind fashion brand Ellie Mae.

A last-minute job interview that led to a romantic relationship and a booming business, no this isn’t out of a Netflix rom-com, it’s the real life story of Ellie Mae Waters and Jeremy Wood-Ross. 

The pair began as colleagues, but since 2016, Waters and Wood-Ross have been navigating growing fashion brand, Ellie Mae, and growing together. For them, being best friends first is the key to staying happy in both business and life. 

In the latest edition of our Power Couple series, Ellie Mae Waters, founder and creative director of Ellie Mae, and Jeremy Wood-Ross, chief executive officer and sales director of Ellie Mae, discuss the challenges and the triumphs of growing a small business with your significant other.[/vc_column_text][vc_column_text]How did you and you two meet? Where were you both in your career paths? 

J: Ellie and I met on a summer day in June 2015. I was driving with a friend to go workout and I got a phone call to come in for an interview with Ellie. I explained that my attire would be less than professional as I was on my way to exercise, but we did the interview anyway. I pulled into the driveway of the office and my friend sat in the car while I went in. This was the first time we met, and I’m convinced the gym clothes helped nail the interview.

E: Jay and I met through work. He was running J.Crew on Bloor street at the time, and I had just started my Ellie Mae journey. We were looking for someone to be our salesperson for all of our wholesale accounts. Someone I was working with at the time suggested Jay, since they had worked together previously. He called him to see if he was available ASAP for an interview and he really did come to our first meeting in his gym clothes! We got along instantly, and I loved the idea of this laidback individual selling our clothes. He really loved the product so I knew he would be able to sell it.

Why did you decide to build a company together?

J: Ellie Mae had decided she wanted to build this business well before I came into the picture, but our journey at the beginning (*referring to a situation in Ellie’s answer) probably helped build the foundation for what is now a great partnership both in the company and in our relationship.

E: We worked together for a while before we even knew we were interested in each other, let alone wanted to build this company together. There were some really unfortunate personnel issues at the beginning of Ellie Mae. Jeremy was the only person who let me in on what was happening when I wasn’t present. He stayed with the brand and me through some really hard times when a lot of people would have just left. I trusted him long before we decided to tackle this together and we always shared the same vision of what we wanted Ellie Mae to be. I love building this company with him. 

Ellie Mae Waters, founder and creative director of Ellie Mae.


Many believe that you should never go into a business with family or a partner. What is your case against this line of thinking? How has it worked in your favour?

J: For us, we started this relationship already connected to the business, so the transition was easier. Normally you’d miss your girlfriend or boyfriend when they go off to work but this way the fun never stops!! I think we have a serious advantage as a team, always being able to collaborate, asking for the other’s opinion and challenging one another. We aren’t yes people to one another which pushes us to be better. There is no doubt in my mind that this type of relationship is not for everyone, but for us it feels pretty natural.

E: The thing about building your own business that I didn’t know before starting out was how much it was going to consume me. My day never ends at 5pm; I bring everything home with me from the office, which consists of a million different thoughts. It was hard coming home alone at the beginning of this and having no one to chat with that really understood what I was feeling or the business as a whole. Being in business with someone who loves it and wants to see it succeed as much as I do has been such a life saver. When I have a moment of creativity that I want to share, he is always ready to listen; if he wants to talk strategy, I always add my piece to it, and when I’m struggling, he understands better than anyone. Having your own business is not for the faint of heart but having someone in your corner going through the shit with you makes it a hell of a lot more fun!

 What have been the major challenges of working with your significant other?

J: Being an entrepreneur has a ton of challenges. Add the learning of that with the learning of a new relationship and you can probably guess the challenges. Over the years we’ve gotten a lot better at separating the work frustration from the relationship, but I’d say that would probably have been the source of any tension in the early days.

E: I think the biggest challenge for me is learning to not take things so personally. Being able to disagree at home and not bring it into the office, as well as being able to have a difference of opinion in business and not bring that home. Keeping everything separate isn’t always the easiest!

Managing a work life balance is hard enough as an entrepreneur or leader of a business. When your home life and work life intersect so thoroughly how do you manage? Do you have a set routine where you define how your energy and time is allocated?

J: When you’re building a business, it is your life. The minute you try to forcefully separate the two, you will find tension. It’s about finding a balance and that balance is different for everyone. Right now, we are in a state of growth, so it feels like there’s less of a balance. We both love the business and really enjoy rolling up our sleeves and getting creative, so the conversations and work can be endless…but don’t worry we also have other interests. I am undefeated in the Nintendo Switch version of Mario Kart, but when we play N64 Ellie puts up a fight.

E: Jay can talk about work forever and not get overwhelmed at all, but I tend to get stressed out. We try our best to enjoy our weekends or date nights with no work talk, but it is hard. We both love it so much that we always end up chatting about some form of work. However, we have gotten better at being more cautious about the timing or place of bringing up a work conversation. My answer is far more serious than his. I prefer his answer!!

How do you cultivate and nourish your relationship apart from working together? 

J: With our work, we’re fortunate to travel all the time. Wherever we go together, we make sure to add a little pleasure with our work. One of the first trips we took together as a couple was to LA. It’s easily the place we go most often and feels kind of like we’ve built a second life there. When we go we usually leave on a Friday and spend the weekend enjoying the weather, going to our favourite restaurants, discovering new hidden gems and hanging out with Juanita, our PR partner in LA, who over the years has become part of our family. It’s been really special having a place like that together where we can go and feel like we’re home. I always look forward to being in LA with Ellie.

E: We always make time for fun. We love escaping to the cottage for a weekend to get refreshed and put the phones away. We are huge Toronto Maple Leaf fans, going to games or watching them at home. If we can, we will add on a few extra days together if we are traveling for work so we can enjoy an adventure! Jay is my favorite human to do nothing and everything with.

How do you support each other as colleagues?

J: We are constantly checking in with one another to make sure we feel supported. I do my best to make sure the design and production teams are supported, and by doing this, Ellie is supported. Ellie’s creative vision is like no other, so making sure she can tap into that is my first priority every day. I find I’m the type of person who always makes sure the team is doing well and takes care of myself last, but I have Ellie and an amazing team who always makes sure I’m supported, too. When we get home and I am working into the evening, Ellie’s always there to make sure I’m eating (which is great because she’s an awesome cook). Ellie always knows when I need the support and without asking, she’s already taken care of me.

E: I think the best way we support each other is by challenging one another. We aren’t yes people which helps us grow professionally and personally.

Describe a moment when the business was going through a difficult time and how you worked together to pull through. 

J: Personnel challenges are usually the difficult times in our business. You’d never think that building a team would be the hardest part but not everyone is cut out for a small business. We’ve been so fortunate to have the core team with us from the beginning, but it’s taken us a few years to (as Ellie puts it) “get the right people on the bus.” We always work together on finding a solution to these challenges, but some are harder than others. I learn so much from Ellie and when it comes to the people side of things, she always brings a really great point of view. I think we often come to a great solution, but it’s not always easy getting there. We’re fortunate to be able to communicate so openly with one another, which I think helps drive incredible results and helps us get through the difficult times.

E: Jay tends to see things before I do. As my mom says, “Jay has great spidey senses.” It is hard finding the right people for your bus. That analogy is one my dad always uses—getting the right people on the bus and making sure they are sitting in the proper seats. I tend to be more emotional about our difficult times and it takes me longer to get to a solution. We both bring different perspectives to the table which is extremely helpful. He is more business and I’m more emotional, so being able to combine the two makes for the best end result. 

How do you navigate disagreements?

E: Disagreements are inevitable. Listening and being respectful is the most helpful in a disagreement. That way you can do your best to understand the other person’s perspective on what you are arguing about. You won’t always agree but compromise will be your best friend!

J: It’s usually Ellie’s way or the highway.

Jeremy Wood-Ross, chief executive officer and sales director of Ellie Mae.

What are your best practices for maintaining a healthy partnership in and outside the office? 

J: I think it’s pretty simple. Just remember the things you both like about each other and your common interests. Find a way to bring that into your every day. We’re making clothes, not saving lives, so it’s important to make sure we’re enjoying the process. The cottage is a place we both love. Getting up there to connect with each other and our families is important to us both. Since spending our summer weekends up north together, Ellie has ignited this passion for tennis I never knew I had. In the summer, we’re basically training for Wimbledon…I’m trying to get Ellie to design us some matching tennis outfits but so far, I’ve had no luck. Matching outfits is a best practice for maintaining a healthy partnership, in my opinion. 

E: Make sure each of you have your own hobbies and friendships—and encourage each other to keep both of those things up. Make sure to take care of yourself so you can be better for each other, and always take time alone. His answer for this question is far better than mine!

What is the most exciting memory you have as a couple that works together?

J: The memories we’ve shared together have honestly been endless. From dealing with a business con-artist, to changing the brand from wholesale to direct to customer, the memories we’ve shared in overcoming these experiences will never be forgotten. I’ll never forget being in New York back in 2016, dragging along 4 massive suitcases filled with our showroom samples on the coldest day in years. We had just signed with this showroom as a way to get US exposure which turned out to be our biggest wholesale order to date. Last year when we were visiting New York, we saw a woman wearing an Ellie Mae in the heart of Soho that she bought as a result of that showroom. That was an extremely cool feeling that we got to experience together. The cherry on top of all of this is that we shared our first kiss that cold night in New York, and we’ve been making memories ever since.

 E: What he said! I can’t top that memory! It really is a good one.

What do you admire most about your partner as a colleague and a partner?

J: How many words am I allowed for this answer…? Ellie’s ability to connect with people is incredible. She has this endearing personality that just draws people in and it’s because she is so genuine that people want to be around her. I’ve never met someone so authentically themselves, not caring what others think, speaking her mind, never trying to be something she isn’t. I find it to be constantly refreshing. I see it in her style, the way she designs collections and how she approaches business. The world is filled with people trying to be something they aren’t or pretending to like things just because they’re told they should, and I find Ellie’s “f*ck you” approach to the trends of society to be contagious. Ellie is a true representation of an unapologetic approach to individuality and I love that about her.

E: Jay is the most patient person I know as a colleague and partner. He is so passionate about what we do that it becomes contagious. Nothing is ever too big or small for him to tackle. He cares so much about the people we work with and loves to nurture all of his relationships. He takes such good care of our business and even better care of me as a partner. He does everything so effortlessly it is annoying. He doesn’t know how to feel anxious or stressed but will listen and try to help when I feel overwhelmed by both of those feelings. I never thought my person in life would also be my person in work, but I couldn’t be happier or more excited to tackle both with him.[/vc_column_text][vc_separator color=”chino” style=”dotted” border_width=”2″][/vc_column][/vc_row]