Catherine Clark: For our listeners who may not know you as well as Jen and I do, take us on a little journey. Who is Emma May? And tell us about SophieGrace.
Emma May: Yeah, for sure. So currently, I’m the founder of SophieGrace, which is a women’s workwear brand. We aim to make things super modular, super comfortable, and really easy to mix and match.
The concept came out of the fact that I’d been a lawyer for a long time – we’ll get back into that – but I wanted things to be easy. Those pieces you reach for on busy days when you don’t want to think about what you’re wearing, and you just know you have staple items that go together really easily. That was the foundation of it.
My background is that I went to law school and practiced, on and off, for about 10 years. I had two kids – I was 28 and 31 when I had them – and I struggled a bit with developing a legal career. I bounced around different versions of that and then ended up going into real estate. I did a real estate career, founded a real estate brokerage, and then bounced out of that because we had a flood in Calgary.
That led me down a bit of a policy rabbit hole – I became a super nerd about it – and thought the policy position the government had taken wasn’t right. I typed out an email that went viral, which led me into the community service world. That then led me to working for Jim Prentice in the Premier’s Office as Executive Director of the Southern Alberta office.
Then we lost an election and, you know, we all got fired. I thought, “Okay, I should do something else,” and that’s when this idea popped up. So that’s kind of the quick and dirty version.
Jennifer Stewart: Obviously you identified that women need a capsule wardrobe that’s easier and more comfortable. But there’s a huge financial and market barrier to entry in the clothing world. What was your thought process around seeing the problem and deciding to actually do something about it – and monetize it – before you launched and bought your first inventory?
Emma May: Well, this is the thing about being ADHD – sometimes there isn’t a lot of thought involved. There’s some impulsivity.
I knew I wanted to do it, and in hindsight, I’m not sure I would have started if I’d fully understood all the hurdles and what it was going to take. But I knew I wanted to do it, and then suddenly it was like, “Okay, to get to the next stage, you need to take out a line of credit for X dollars and order 32 boxes of inventory to do this at the scale you want.”
That was a real decision-tree moment where I thought, “I just have to do this and trust that my margins are strong, trust that I can market it, and trust that I’ll figure it out.” I’d love to say I had a perfectly executed financial model before I started, but the reality is I didn’t. I have a really good one now, but back then I kind of just went for it.
And honestly, that might be the only way to do it, because I’m not sure you’d ever start if you knew everything. There was also this feeling of needing to prove it – to prove that it would work and that it would be a real thing. That meant taking on a level of financial risk that I had to be willing to endure.
Catherine Clark: I was just going to ask, would you say you’re a risk-taker?
Emma May: Yeah, definitely. I’m okay with risk. I think now I’m carrying a level of daily risk that’s pretty uncomfortable, but I’ve always been a risk-taker.
I hitchhiked through Guatemala by myself when I was 18. I’ve done some pretty batshit crazy things over my life, which have generally worked out – sometimes not so much. But yeah, I think being a risk-taker is built into my DNA, which is a bit scary.
Jennifer Stewart: Was there a moment after you launched – when the brand became successful and you saw politicians and celebrities wearing it – where you thought, “Okay, what’s next?” Or did that just motivate you to take the brand even further?
Emma May: What’s interesting about this project is that it’s so multifaceted and constantly changing that it actually works really well with ADHD. It’s always like, “What’s the thing today?” This ad works today, that one doesn’t tomorrow, so we need a new one. Now we’re working on a new product line. Innovation is built into every part of it.
Nothing is slow. Last year we dealt with tariffs, and my COO and head of product and I managed our way through that. When we finally got to the other side, I remember saying to her, “What would we do if this was boring?” And she said, “Oh, I’d quit.”
Catherine Clark: Building on that – there’s something to be said for reaching a point where you’re just tired. Tired of constant decisions, reacting on the fly, or dealing with issues as they arise. How do you keep putting one foot in front of the other in those moments?
Emma May:I have those moments all the time, to varying degrees. A lot of it comes down to personal wellness – taking care of my mental health so I’m not dealing with unnecessary noise and can focus on what’s right in front of me.
One, it’s really hard. Two, I have accountability. I have external investors – not a ton – and even though I’m still the majority shareholder, I’m accountable to them. My customers keep me in check too. I get notes from them all the time, and it personalizes everything. It reinforces the “why.”
You can be having a really shitty week, and then you get a note from someone saying the brand made their life easier, and you think, “Okay, the customer gets it.” That feels really good – for me and for the team. I also look at the team and all the work they’ve put in, and that responsibility to others keeps me motivated.
Internally, I have a long-term goal for where I want the company to get to. I’m not sure yet if that’s purely financial or more of a personal milestone in my mind. The financial side obviously reflects progress, but I haven’t fully defined that yet.
Day to day, it’s also about making sure I’m exercising, eating well, and sleeping. I’ve become really nerdy about all of that. I’m on HRT, I’m on all of it. I don’t want to say I’ve fully gone down the optimization path that a lot of guys do, but there’s definitely an element of that in my life that helps me stay mentally strong.
Catherine Clark: And just for younger women listening, HRT is hormone replacement therapy, and it’s something they get to look forward to.
Jennifer Stewart: How do you quiet the noise when your gut or intuition is telling you, “This isn’t right, and this is the path I should go down”? You probably get a lot of advice, feedback, and direction about where the brand should go.
Emma May: Honestly, I spent my morning on that exact call – with my head of product. We wanted to sit down and review what we’re doing over the next year, and also look at the bigger goals we want to achieve. That conversation really came down to excellence.
Sometimes speed and excellence don’t go hand in hand, and there’s pressure to execute at a certain pace. What’s really interesting is that this is a very current topic – this is actually what Lululemon has just been going through. It’s about product innovation, excellence, and designing specifically for a very particular customer.
At the same time, you have cash flow requirements. You have to keep up with the pressure to continue making sales and performing. On the flip side of that, for me, it’s about fabric innovation. We haven’t yet had the chance to really do our own fabric innovation, and that’s always been something we’ve had to navigate – pushing with what’s available, sourcing carefully, and working really hard within those constraints.
As we get deeper into this, we’re realizing we have a really interesting customer, and we want to serve her in a very specific way. That likely involves doing fabric innovation work that we haven’t done in the past. That’s what will really help us dial into what we know our customer wants.
We’re lucky because we have a very specific customer, and she tells us what she likes, what she doesn’t like, and what her needs are. In many ways, I’ve lived that life. I’ve gone to conferences and been annoyed when I have to pin the stupid thing onto my shirt. You’re packing and you want things that actually work in that environment – things that hold up over time but still look elevated. You don’t want to show up looking like you just turned a sweatsuit into a suit. It still has to look and feel like a different product.
So for me, it’s this constant tension between the business side – margins, marketing, spend allocation, operations, and maintaining a clear strategic perspective – and the creative side. That creative side is about innovation, diligence, testing, and really drilling down to make sure you’re delivering at that level. Those are the tensions we work through every day: how do we deliver on all of it?
Catherine Clark: One of the toughest things people talk about in leadership roles is managing other people. You’ve grown to a stage where you’re working with a team – how have you approached that kind of leadership?
Emma May: I’m not good at it. I’ll just say that. I really don’t like managing other people.
What I’ve learned is that I need to work very closely with a certain kind of person – people who work well with me. Over the years, I’ve realized I work extremely well with very detailed people who aren’t necessarily big-picture thinkers or the ones coming up with concepts and ideas, but who have a strong ability to dig in and execute.
When I look back over my career, the moments where I’ve had the most success are when I’ve been paired with someone who’s the yin to my yang. That’s when I execute really well – when I can clearly hand off certain parts of the work and take ownership of the parts I’m best at.
So for me, leadership and people management is really about finding the people I work with most directly who are okay with a bit of my chaos – because they’ll organize it themselves.
