Dorsey’s Meg Strachan Knows Good Business

In ELLE’s series Office Hours, we ask people in powerful positions to take us through their first jobs, worst jobs, and everything in between. This month, we spoke with Meg Strachan, the founder of jewelry brand Dorsey, named after her grandmother. After an extensive résumé of leading direct-to-consumer brands in the heyday of venture-backed growth, Strachan started Dorsey in 2019, just as a very different era of business began. It hasn’t been easy, but for Strachan, it’s been necessary. Here, she discusses the advice that kept her on track and the power of embracing change in business and in life.

My first job

I was a hostess at the California Cafe when I was 16.

My worst job

I was really bad at hostessing. I didn’t understand the politics of where people are sat, how they’re sat, and the internal restaurant politics. I feel like nobody was ever happy with where I sat them. I was a waitress at a point too, and you learn so much about handling customer feedback in real time. Everyone should work in hospitality. Until you do it, you don’t have a real appreciation for the other side. It’s been very helpful in running a business.

The pathway to my current role

My direct-to-consumer journey really started in my late twenties. I worked for a number of companies that were part of the original direct-to-consumer businesses when venture capital was investing in D-to-C, like 2015 onwards. I was the CMO at Anine Bing early on in the business. I worked at Goop early on. I was at a company called JustFab, which acquired another company called ShoeDazzle. I worked for Carbon38, Girlfriend Collective, Bandier.

I’ve really seen it all when it comes to those years between 2015 and 2025: 2015 to 2020 were the glory days of direct-to-consumer, and then 2020 to 2025 is when I started Dorsey and I had a very different experience. I had been privy to what it felt like to build a company when things are thriving, when there’s a lot of energy and a lot of room for air.

When I started my company, it was really leading into a very different time. But I ended up at the tail end of wanting to work for other people, and wanting to build other people’s businesses. Since I was 9 years old, this is always what I wanted to do with my life. I felt very lucky. I love the business of building businesses. The product that we sell, jewelry, is because of my preference. My grandmother’s name was Dorsey and so many of us love jewelry because of the women in our lives.

The decision that could’ve changed everything

When you’re building anything, the amount of self-doubt that you’re working through on a daily basis is bottomless, and you’re your own worst enemy at 3:00 in the morning. You can talk yourself into or out of anything. It’s true for all projects, whether you’re starting a Substack or you’re building a business. There were multiple times along the way when I almost quit. Sometimes you want the people around you to give you permission to quit, right?

The voices that you surround yourself with while you’re doing anything are really critical and important. There was one point where I just thought I couldn’t do it anymore. I was exhausted. And I called somebody, and I happened to call the right person, and they talked me off the ledge. It was an old colleague of mine. A single conversation can change the whole trajectory of what you do and don’t do in life. I always think if I had called somebody else, maybe I would have made a different decision. I like to think I would have gotten through it, but there are just so many inflection moments in life. In a business, it’s really important who you pick up the phone and call.

The life-changing advice I got

[The colleague I called was] so not fazed by how I was feeling. And they didn’t try to commiserate. They just said, “What you’re feeling is normal. Take a few days off. And then call me back.” It was maybe not even the most profound advice, but it was just someone saying, “Of course you feel the way you feel. You’re supposed to feel the way you feel right now, doing what you’re trying to do. Congratulations, you’re on a normal path.” I rarely talk about being tired anymore and I just feel grateful.

What I learned from working at other brands

The thing I learned most is that no business is the same. I would be in one position somewhere, learn a business, what makes it work, what doesn’t work, what customers like, what creative works, and then I would go to another business and think I can apply the same principles. You come into it feeling like you’ve got the answers. You have experience, but you don’t have the answers, because every business is so different. You can’t apply the same strategies from one business to the next. It takes a lot of time to figure out what works.

The most positive thing is that all those companies were making it up as they went. From the outside, you’ve got this big logo and it seems like everything is moving in a very specific direction and there’s a lot of strategy. When you’re in the company, you realize that every team is sitting at a conference table trying to figure out the next step forward, working behind schedule, or maybe ahead of schedule at some points, but everybody is making it up as they go. That was the single most comforting thing for me in building Dorsey, was that I knew that in all these other companies, they’re doing the exact same thing. Nobody has a silver bullet.

What surprised me about the jewelry industry

It’s not an industry that questions itself. They’re very dedicated to the way that things are done and how they’ve always been done. It’s very male-dominated, which I didn’t understand, because so many times the consumer is typically female. It really is an industry that is run by men. It’s all men in suits. Where are the women? They’re really not there the same way. And for some reason, I’m not surprised by it anymore. I go into these meetings and they’re like, “You want to do what? Well, nobody does that.” I say, “Let’s just do it, because I feel like it makes sense.” I realize that nobody else has done this before, but I don’t care. Let’s just try it. It was interesting to be an outsider who didn’t know that I was asking for things that were so strange to an industry that’s worked a certain way for so long. It was extremely beneficial in the long term for us because we ended up defining our own path forward and we’re still doing that today.

How the Dorsey customer has evolved

We have evolved so much. We really know our customers. When I started the business—when you start any company—your 3:00 in the morning thought is, “Is anybody gonna buy this?” You have to move forward on a hunch. And you have to move forward for a really long time on a hunch, too. You have early adopters and you have people who love what you’re doing. Our first customer is still a customer of ours today. I took her order. I couldn’t believe it didn’t come from friends and family. I packaged it up in my house. I drove to USPS. I filled out a form to ship it.

In those very early days, the lab-grown diamond was really new. The customer is much more aware now. She knows how she feels about it or is forming her own feelings. Lab-grown was an industry that was very looked down on and not just by consumers, but by the industry itself, and that has changed. Our consumer has really evolved with us and has been so supportive.

My biggest career lesson

It never gets easier. Every year is really different. You think that when this happens, then it’ll be easier. When that happens, then it’ll be easier. When this happens, then I’ll be happier. From a business perspective, I would say that every year is harder and in different ways. The role I have running my company changes every single year. Just when I get good at what I’m really focused on or certain problems, there’s a shift. And usually there’s a crisis about every six months. We’ve learned to know that there’s always something that’s coming that you haven’t planned for and the climate of the world right now has made that much more frequent. It doesn’t get easier. It just changes.

The last crisis I dealt with

There have been so many. There’ve just been layers and layers of changes that have happened over the last couple of years that I think have changed everything. We’re at a point as a business that one change creates 12 others and sometimes I learn about those changes on a moment’s notice. I’ve learned so much over the last few years about how important it is to approach the next years as different types of headwinds. When you’re prepared and you put your life vest on, if you’re expecting it, it feels really different.

I’m such a different person than I was five or six years ago. We work really hard and we’ll be doing that every single day, regardless of the year before. It’s all one big learning experience in an effort to build something great. It really takes being okay with the unknown. And that’s a big thing to become okay with. That’s just part of business, part of life, part of everything.

This interview has been condensed and edited for clarity.