Feminist Founders Subscriber-Only Podcast

Welcome to the Feminist Founders audio series event. This is a bonus for paid subscribers of the Feminist Founders newsletter. So if you're here, thank you so much for your support. I'm excited to bring you this series, featuring incredible thought leaders who will share insights about doing business differently in a way that honors equity and social justice. I hope you learn a lot from this. Let's dig in.
Becky Mollenkamp: Howdy, thank you again for being a paid subscriber and for being part of this audio series. I'm so grateful to have you here and very thrilled to introduce you to Dacy Gillespie of Unflattering on Substack. Her business is called Mindful Closet. I may not be introducing you to her—in fact, she may have introduced you to me because her following is much larger than mine, both on Substack and Instagram. She’s got like 9,000, maybe more, subscribers on Substack at this point. That’s why I invited her to talk about her Substack journey because it's really interesting, especially for anyone interested in Substack, to hear from people who are doing it and having success. It’s not always easy, and I know Dacy well—I’ve known her for more than a decade. We live in the same city, we were in a mastermind that met in person weekly for years, and we still get together for co-working dates and coffee chats. I’ve seen her have her kids, I’ve seen her grow her business, and I’ve seen her start this newsletter. We had coffee and talked about it. In fact, she’s the one who motivated me to make the switch to Substack, so I’m very grateful to her for that. I think it’s wonderful how open and honest she is about her journey onto Substack—what’s worked, what hasn’t, how it’s felt—all the things. So I hope you enjoy this, and make sure, if you don’t already, to go subscribe to Unflattering if you're at all interested in style or in how to feel better in your clothing. Dacy is a very different kind of stylist. It’s not about judgment, trends, or what’s flattering—hence the name Unflattering—because it’s all about what feels good for you and how to express yourself through clothes in a way that makes you feel really good. So go check her out, but first, take a listen to this wonderful conversation that we had.
Becky Mollenkamp: Dacy, my friend, thank you for being part of this series. Your podcast episode has been very popular, and you have a magic touch on Substack. Anytime you comment on something I’ve written or share it, I get a flood of new subscribers because you have grown quite a wonderful and seemingly loyal following on Substack. That’s why it’s perfect for us to talk about Substack and your experience here with Substack growth for this conversation. To kick things off, can you tell us a little bit about your decision to move to Substack? I know your journey started a little before mine, and you were part of my inspiration in saying, “Just do it, Becky,” and making my own move here. I think your anniversary date was maybe back in April or May, so you've been on Substack for a little over a year. Can you take us back to that time, a little more than a year ago, when you were trying to decide whether you wanted to go to Substack and the thought process around that?
Dacy Gillespie: First of all, Becky, thanks for having me. This is a fun way to do an interview, and I’m excited about this. And yeah, I’d love to talk about how I decided to move to Substack. So, as you know, and maybe some of your readers know as well because I’ve written about it for your Substack, I have a pretty low capacity and low energy for work. I’m always looking for ways to do work that gets out into the world without adding to the amount of work I already have to do. I had gotten into a pretty good rhythm with my email newsletter, where I was emailing most weeks. Every few emails would be a longer, more intensive think piece, if you will, and I had always gotten great responses and resonated with those longer emails.
I would get responses to those, and I would think, “This is lovely; I’m so glad this person is feeling this way,” but they didn’t know that person X over here had also written me that they felt the same way. It was almost like ships passing in the night. So, I thought, “How great would it be if I could do this newsletter that I’m already doing, and people could comment on it and interact with each other?” At the same time, I wouldn’t be adding any more work to my plate because I was already doing this, and if I could get five people paying me $5 a month for something I’m already doing, that’s just gravy—a bonus. So, those were my main reasons for setting up a Substack: uncovering a new revenue stream that didn’t add to my plate, having a place where my readers could communicate with each other, and the fact that I was already doing it, which made it easier. Really, the only hurdle was figuring out how to set it all up, and that definitely was a big project, but yeah, I’m pretty glad I did.
Becky Mollenkamp: You said that a year ago, when you were thinking about this move to Substack, you were just thinking, “If I can get five people to pay me $5 a month, that’ll be awesome.” You have clearly blown through that. I think you’re at 9,000+ subscribers now, and more than 5,000 of those you’ve added just in this year that you’ve been on Substack because you came in with like 3,500. Of the 9,000, about 500 are paying subscribers. In that one-year post you recently shared, you talked about making $13,000 before taxes in year one, and you even announced a new membership level that I’m sure has also helped increase that income. For a lot of people, those numbers sound really enviable, myself included, because my Substack’s nowhere near there. I know you mentioned that setting up the Substack took time and some frustration, but once you got past that hurdle, let’s talk about where you are now. Your hope was that once you got through the setup, switching from your previous email marketing to Substack wouldn’t add anything to your plate. Is that proving to be true? Are you basically adding $13,000 a year or more in income to do a similar amount of work as you were previously doing with email marketing that you were paying to do, or has it been more work than you expected?
Dacy Gillespie: Oh my gosh, it’s been so much more work. I mean, which is partially due to what I’ve decided to do. I could have just put out these once-a-week kind of things. I knew I wanted to be really consistent, and I knew I wanted to foster that community, so in addition to having an email every week, I have a discussion thread every week, usually related to the email. Both of those things take a lot of time because one thing I didn’t factor in is that I have to engage and respond to all the comments, which I do almost always, to pretty much every comment. Then I added this new level, as you mentioned, which has been a huge amount of work. Even some of the emails I send now require more work than I was used to, and even just formatting Substack—it’s probably similar to the amount of work on ActiveCampaign, which was my old email marketing system—but it always shocks me how long it takes. The post may be written, proofread, and edited, but it still takes me over an hour to get it scheduled on Substack because I have to put in links, images, and buttons to subscribe, among other things. So, no, I’d say it’s a lot more work than I anticipated. But a couple of things keep me going: people are engaging, and it has become another revenue stream.
Becky Mollenkamp: I had a sneaking suspicion that it was more work because it just seems like it would be, especially as you grow in subscriber count and have more paid subscribers and want to deliver things for them. You mentioned that you have discussion threads, and part of what appeals to many people about Substack is that, in theory, it has more opportunity for community building than just an email list. Your normal email list is you email them, maybe they can email you back, and that’s it. Inside a Substack, they can comment, and if you allow it, other people can reply to the comments, not just you. So they can begin to have conversations beyond just you or that are larger than just you and the reader. Is that part of what appealed to you about Substack? What are you finding about the community element of Substack? Is it working well for you? Besides the posting and writing, is the community management piece a heavy workload? I would love to hear you talk about what you’re discovering as you build up a more sizable community on Substack, and if that is something worthwhile or maybe more work than it’s worth.
Dacy Gillespie: I mean, it’s absolutely worthwhile, that’s for sure. It does definitely add to the work. As I said, I do have to schedule those posts, sorry, those threads. It doesn’t take a ton of work, but I do have to come up with the topic of the thread, and then, as I said, I really try to engage as much as possible because I think that helps build community. But I’m finding it lovely. People are super kind and supportive of each other. I think I even wish there was a bit more—I think you always want a little bit more—and I definitely make the mistake sometimes of looking at other people’s threads and seeing how much engagement they have. But I definitely have a core group of people who are very active there, and while it adds to the work, it’s absolutely worthwhile.
Becky Mollenkamp: OK, here comes the big question—the one that I think everyone will be eager to hear the answer to. As someone who has grown significantly in a year, I know you moved over something like 3,000ish subscribers, and now you’re moving in on 10,000. So, a big chunk of that was new subscribers, not just the people you already had. I’m wondering if you could share how much of that comes from people finding you on your website, social media, or other places where you’re active, and then subscribing versus how much of that is coming through collaborations or recommendations, or internal search within Substack. Do you have an idea of how much of that growth is because of the Substack network versus your own efforts putting people there? And could you also share a little about collaborations? What has that been like, how has it helped with your growth, and what kinds of things have you been doing over the last year with collaborations? How much has that contributed to the success you’re having.
Dacy Gillespie: So, I've never been great at keeping data or tracking it. To be honest, I'm not sure where all my traffic is coming from, but I can tell you what my sense is. I believe that most of it is coming from within Substack. A good portion comes from other Substacks that recommend mine. Some of it is just organic discovery on Substack, and other people may be sharing some of my posts and notes. I don’t get the sense that I get much traffic from social media or my website. In fact, from my website, I probably get almost none. Well, that's not entirely true; I would have to track those numbers down, but I don’t get a ton from Instagram. It seems more and more that my audiences are diverging a bit—there’s the Instagram audience and the Substack audience. So, yeah, I think probably the large majority of it is coming from within Substack.
In terms of collaboration, I’ve tried to create relationships with other writers on Substack. I mean, I definitely partially got onto Substack because of a client/friend, Virginia Smith, who really supported me a lot when I got on and has supported me throughout. In fact, it would be crazy to see how many of my subscribers are also her subscribers because she drops my name in a lot of her posts. We just did a three-week-long collaboration style challenge together. She writes Burnt Toast, which is a very popular Substack. I also created my own series called Style Stories, which is a piece of how I work with all my clients. I’ve been asking other Substackers to participate; I basically just have a questionnaire that I send them, they fill it out, and then I share it on my Substack, linking to theirs, and hopefully, they link back to me. So, yeah, those are a few ways. There are also a few people whose Substacks I really try to engage with and make close ties with some of the writers. That has certainly been very, very helpful.
Becky Mollenkamp: I can see all the collaborations you do, and I know that when you comment on something of mine or share it, it definitely makes a difference in subscribers. What I’m learning about Substack is that collaborations are a really important piece of it, but not the only piece. I’m wondering, over your last year, if you could share any lessons learned—things you would have done differently, things you wish you hadn’t done, things you still want to do more of that have worked well. Do you have any advice for newer folks coming onto the platform, or anyone trying to monetize content in this way? Specifically, I’m talking about getting new subscribers, but probably even more important, converting people to paid subscribers, because that’s obviously the perk of this kind of newsletter format. Anything you can share about that part—getting more people to pay—would be most interesting, but general advice on growing your Substack is great too.
Dacy Gillespie: Just off the top of my head, and this is not to sound like I did everything right, but I can’t really think of anything I would have done differently. I put a lot of thought and intention into it and did a lot of research, talked to several other Substackers before I started, and I feel like I did pretty well. If anything, I wouldn’t say I regret this because it wasn’t possible, but I still have a list of things on my Trello board that I can do to supposedly maximize my Substack, but I just don’t have the time or energy to implement them. As far as getting new subscribers, I think the recommendation aspect of Substack has been incredibly helpful. Certain Substacks can recommend yours, and each Substack basically has a list of the Substacks they recommend. I think a lot of people depend on those to find new things to read, and that’s been super helpful for me.
As for converting subscribers from free to paid, I think you just have to find that thing that they feel is worth the money. For me, early on, I knew that was going to be my shopping links. In my newsletters and on social media, I’ve always done roundups of cool stuff I come across while shopping for clients, even if it’s not right for them, but I still want to share it. Those link roundups have always been part of my email marketing or social media, so I knew going onto Substack that would be something I’d put behind a paywall. Now, my archives are for paid subscribers after two weeks. People can read my stuff for free, but after about two weeks, it goes behind a paywall. I do a lot of backlinking, linking to previous posts I’ve written. Honestly, I don’t know if that’s had any effect; I’d have to look into that. For some people, they put more personal stuff behind a paywall, or they put the transparent numbers of their business behind it. Those are the types of things, or some really valuable resource, that people would value enough to pay $5 a month for, or whatever your price is. That’s been really helpful for me.
Becky Mollenkamp: How do you now feel about Substack as part of your business? Is it becoming the main focus of your business? Is it in support of your styling work? Is it supporting that, or do you have two different businesses now? I’m curious how you see Substack fitting into what you’re doing with your business.
Dacy Gillespie: I definitely don’t feel that Substack is my main job, nor do I ever want it to be. I have to constantly remind myself of that when I compare myself to writers for whom full-time writing is their career. Writers on Substack have intricately researched pieces, conduct interviews, and write long-form content. I have to remind myself that this is really just in support of my business. For me, it’s still marketing, essentially. It’s still meant to drive people towards my services. As I’ve said over and over, if I can get a little bit of income along the way of doing what I would already be doing to market my business, then great. However, I do see it as a very important part of diversifying income streams—getting all businessy—because most people’s businesses are up and down, and mine is no exception. It’s very nice to cultivate one or two things that are steady streams of income. So, yeah, Substack supports my work, hopefully spreads the message of my work to more people, and in turn, my content comes from my work. I’ll be writing about things that come up with questions I’m asked, issues I come across with clients, and all that kind of stuff. So, they’re pretty symbiotic.
Becky Mollenkamp: Can you give us any behind-the-scenes peeks at what plans you have moving forward? What are you expecting year two to bring for your Substack? Are there any changes coming up?
Dacy Gillespie: I kind of just frantically implemented a bunch of changes, growth, and upgrades to my Substack. I say frantic because I realized that the one-year anniversary of my Substack was coming up, and I had a bunch of plans percolating, and that anniversary would be the perfect time to launch them. I realized this about four or five days before that anniversary post, and that’s what I foresee continuing into year two. What I did was create a new membership level for my Unflattering newsletter, where people at that level get more access to me. I make specific personal recommendations for them, they get access to several of my courses, and they get access to a big resource I cultivate—my spreadsheet of retailers with the ability to sort them by size, price, style, and whether or not they’re sustainable. I just pulled that together real quick a few weeks ago, and that launch went well. Honestly, at the moment, I haven’t looked much further than that.
Becky Mollenkamp: Thank you so much, Dacy, for participating in this and for all your help. I just want to wrap up by having you share the best ways for people to find you and learn more about you.
Dacy Gillespie: This was a fun way to interact, even if it was a bit of a learning curve for me. So, thank you for inviting me to do this and for having such a creative way to do an interview. That’s really cool. People can find me—since we’re talking about Substack—my Substack is called Unflattering, and the URL is dacygillespie.substack.com. I’m also pretty active on Instagram at @MindfulCloset, and my website is mindfulcloset.com. So, come find me in any of those places.
Becky Mollenkamp: Thank you, Dacy. I love Dacy so much, and I’m so grateful to her for doing this. I hope that you took away some great nuggets from her interview, and I thank you so much for listening. Again, thank you for being a paid subscriber. You’re amazing. I’ll be dropping another new private episode in your podcast feed for you tomorrow. Thank you for listening.