Main Street Makers

#4 Marty McDonald: Turning self-doubt into powerful action

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In this engaging conversation, Marty McDonald shares her bold entrepreneurial journey. Learn how one cold email to Target got her placed in over 400 stores. She discusses business challenges faced by entrepreneurs, particularly women of color, while also emphasizing the importance of community building, mindset, and self-advocacy.


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to really rewrite my mindset from employee to entrepreneur. I had to learn how to bet on myself every day, bet on myself when I didn't feel like it, bet on myself when I wanted to stay in the bed, bet on myself when things weren't going right and people were telling me no, no, no. I still had to choose to bet on myself. Today we're really excited to welcome Marty McDonald CEO of Boss Women Media and L Olivia to the podcast. Welcome Marty. We're so excited to have you. Thank you so much for having me. I'm so excited to be here. Well, we're really lucky to have you because you're a serial entrepreneur, as I understand it. You've been in business for seven years and you've started a couple different types of businesses. You have the fashion and retail business, then you also have your media business. So I'd love to just have you talk about your entrepreneurship journey. How did you find entrepreneurship? What led you to starting businesses? Why is this your calling? You know, I believe that most folks start businesses out of frustration and necessity. And I was in the intersection of both of those things. I was working in corporate America. I wasn't feeling seen. I wasn't fulfilled. And I realized, like so many ambitious women, especially women of color in some instances feel the same way. Right. And I remember going to networking events when I was sitting in corporate America trying to navigate like, how do I find myself? How do I find my space? Where do I exist? Where does the job title I want to land? Right? by the way, are there other folks who look like me that have achieved these things that I can see myself through? And I remember going to these events and everybody wearing black, blue and gray, right? Like just feeling like, man, this cannot be it. Who deemed this to be success, right? And me really getting connected with my inner voice and finding, okay, there is more. I don't see it, but I have to create a pathway to craft my more. And I have to do that by building community. Community is how I'm going to be able to exit the space that I don't see myself existing in. to be able to then showcase this to other folks so they can see what's possible for themselves, right? And so December 1st, 2017, I quit my corporate job. I'll never forget the day. Market is a time in history where I actually found a pathway to my purpose. I didn't find my purpose at that time, but I found a pathway to it. And that pathway was betting on myself. I said, you know what, I'm gonna go all in and I'm just going to bet on myself. What could happen if I put myself in the forefront of going after my own ambitions, my own dreams, my own goals, instead of creating a space where I was going after and doing that for someone else? And so that's how Boss Women Media was formed. It was formed to be a space, a safe space. for women to see what was possible through the lens of other women. Whether those women were sitting in corporate America and they were building incredible careers or they were entrepreneurs and they were not, they were not taking no for an answer. They were creating a pathway for themselves. They were doing it with limited resources. They were doing it not knowing the right folks. And I wanted people to not just be motivated by that, but I wanted to be able to create a space where discipline could take the forefront of women standing in what was possible. And so that's how we got to boss women media. The story of L Olivia is completely complex and completely different, but it also was grounded in frustration and necessity. When I got pregnant with my first daughter, in 2020, we were in the middle of a pandemic. And when I was 24 weeks pregnant, I got diagnosed with something called congenital diaphragmic hernia of her specifically, which basically meant that her liver, her spleen and her intestines were in her chest and they were covering her lungs. And my whole birth plan changed from this happening to us. And so, Instead of me thinking that we were going to deliver at the private hospital, we ended up having to deliver at the county hospital. And the county hospital created an interesting dynamic and experience for me as a mother to understand that there are some systematic issues that happen in health care. And it made me pull up and learn what type of mother I needed to be to advocate for her life. And one of the first lessons that I learned was advocacy was the tool that I would have to invest in my daughter because I was advocating for her life daily and that representation isn't synonymous. It's something that must be seen in this world. There are all types of people in this world and all types of diversity in this world and that we should be able to lean into the equity of that. And so L Olivia was birthed from this space of I want my daughter to be seen. After we left the NICU, we stayed in it for about 35 days. We brought our baby home. We got the surgery. We moved everything in the right place. We're good. I remember going into Target and I was looking for a character that looked like my daughter and I didn't see it. And when I left Target that day, out of frustration, And necessity, I said, I'm going to go create a character brand that my daughter gets to see herself through. I want her to see what's possible. I want a character that talks about her future and the possibilities of dreaming big. And I want her to be equipped with the tools of advocacy and representation that she will need to be successful in her life. And that's how El Olivo was started. Yeah. That's beautiful. There's so much there. I love how you kind of just went out on your own and made it happen instead of like waiting for it to happen to you and like really focused on just creating these safe spaces for other women so that they don't have to experience the same things that you did. That's really wonderful. And I really feel like relatable for a lot of people. know Levi has a story. He says that the first day he struck out on his own was like the day life began. So I think that resonates with a lot of people. I think that resonates from so many different lanes because we think that life is supposed to be this one way street. There's so much to life, right? And it exists for us to live it, not just do it. It's existing for us to live it, to be a part of it, to create the values, to show up how we want to. But somewhere along the way, someone's told us that it can only exist in this way. And I think that we're living in a time with a generation of people who are showcasing that there doesn't have to be society norms of expectation for your life, that you can live it to its completeness. Yeah, that's beautiful. I love that. I do want to go back to your origin story and how you started Bosswoman Media. Did you start that as you were working or did you just fully bet on yourself, go out on your own and like the day you quit your job was the day that you started that business? So no, I worked on Boston Women Media for two years before I quit. And so before I took the leap out and quit my job, I had been working on it for two years. I had been testing. I remember my first event. The first event that I produced, I had 25 women show up. And it was something so magical that happened when we, as these women, communed together. There were experiences shared, there was lessons learned, but... Most importantly, what I learned is that people are craving community. And I think that still is to this day, if not more than ever before. People are craving in real life, touch me, feel me experiences. And so that first event was like, OK, if I can do this 10 times over, I think I got something here. If I can build this from 25 women to now. hundred thousand women. I I got something here, right? And I just kept taking one step at a time. I invested in going to other events so that I could get learnings from to understand how business revenue was being made. I put myself in circles with people that I hadn't necessarily networked with before. I was completely open to the process. I wanted to win incredibly bad and I had a vision that was so clear that nothing was going to stop me from making this thing happen even if I didn't know every step I was going to take along the way. Yeah, that's amazing. I love that you kind of transitioned and it's possible for you to kind of do both at the same time and test and learn before you kind of go out on your own. highly recommend it. Yeah. So could you also talk to me about some of the challenges of those early days in the first business? What were some of those challenges and how did you work to overcome them? think one of the, there's two things, right? It was the security of a paycheck, right? Like, girl, you're not getting no paycheck no more. You got to figure out how to get a paycheck yourself, right? And then stepping into the uncertainty of it all, right? I had to really rewrite my mindset from employee to entrepreneur. What did that look like, right? How was I managing my time effectively, right? How was I making the right connections? How was I creating with very little resources? But in changing my mindset, I had to learn how to bet on myself every day. on myself when I didn't feel like it. Bet on myself when I wanted to stay in the bed. Bet on myself when things weren't going right and people were telling me no, no, no. I still had to choose to bet on myself. And the thing that shifted me understanding how to do that was establishing a morning routine. I think that any impactful leader understands that your mornings are your non-negotiable. The first thing that you put into your day is how you're going to react throughout the day. So instead for me of being reactive to Instagram and watching everybody else's highlight reel, instead of me being reactive to my email of No, I'm not interested, no responses or an influx of emails. I decided to establish what am I grateful for today? What is the intention that I am setting for myself today? What am I praying for? Right? It was when I incorporated my morning routine. it shifted the mindset that I was bringing to the day and I was being more in control. Cause there's only a couple of things that you are in control of. You're in control of how you respond. You're in control of how you feel and you're in control of the actions that you take. And so for me, it was really guiding myself in that mindset of My non-negotiable is tackling my day in a manner that sets me up for success, which means I have to prepare for that the night before. And in the preparation, it's going to lead me to transition well as an entrepreneur, as a leader, as a thought leader in the marketplace, as someone who not only has a vision but knows how to execute the vision. Those were the early days. It was putting that framework together in order for me to be successful. Yeah, that's amazing. feel like so many business owners, so many leaders have a hard time not being reactive to the things that they get in the morning because people need you, they need things, they need answers. So it's incredible that you found that it was important to create that space for yourself in the morning. Was there any like kind of mental challenges that came along with that? Because I'm sure, you know, you just woke up to so many messages and you have a social media business. So you were probably checking because you're on social media. So I'd to get a little more insight from you on that. I think the biggest hurdle that I faced was the story I was telling myself. And I think that we all can relate. Everybody has a story that they're telling themselves, whether that story is good or bad. And for me, my story was working against me and not for me. I was telling myself a doomsday story in some ways that I wasn't gonna win, although I was choosing to win. It was working against me. While I did the work, I still in some ways didn't believe that they would, which I have no control over if they will. But what I do have control over is the story I tell myself, right? The story that opportunity exists, the story that financial freedom will be a part of my journey, the story that I will create generational wealth for my family, right? And so for me, it was rewriting and rewiring. And what I had to do was I had to make an investment in that. I hired a performance coach. My performance coach really helped me identify the story I was telling myself, where the story came from, which was a lack in my childhood. I grew up in a pervished environment, right? I was the first generation to go to college, right? First gen in college. come from a mother who was in and out of jobs. She was a single parent household, right? And so I was going against the grain on everything. I had never seen my success exist firsthand. I didn't see it in my parents. I didn't see it in a family member necessarily, right? So I had a lot of traumas that I had to really rework in my story of abandonment, of loneliness, of lack. that really helped me shift the story of actually, Marty is the sauce. I'm bringing the sauce. I'm delivering it, right? What I deliver isn't impacting just me, it's impacting communities around me. And that's why you should be a part of it, right? And so it was a ton of mindset shifting. It was a ton of work around that. I think that that's where folks fail to invest in. at those early stages. If you make that investment around you and how you can deliver and what you are able to believe, not just from a motivational perspective, but from a discipline perspective, that's how you are able to create success in whatever it is that you do. Whether you're a leader at a corporation or you want to build a thriving eight, nine, 10 figure business. That's so true because everything comes from you and so you need to make sure that you're able to be in peak performance if you want to actually deliver and achieve your dreams. So that's really important. I'm curious, so that's kind of the challenges of when you were very new to entrepreneurship. How was starting your second business, El Olivia, different? Because I could imagine that you had more resources, you had your mindset in place. What was that like? Yeah, yeah. So I'm four years in business at the time when I started L. Olivia. Four or five years, I started in 2022. And so this is how I started L. Olivia. And I think that this is it could be an interesting blueprint for someone because you just never know what opportunities exist. And I started L. Olivia, I share, I went into Target, I was looking for something. There was tons of gaps on the floor. I left there with a clear vision of exactly what I was gonna create, specifically for toddlers, specifically little girl toddlers, right? And with that being said, I did all of the things that I couldn't start boss with, but now I had the resources to start Olivia with. So I did the whole brand kit, the marketing campaign, hired the influencers, right? built out the campaign, did my first launch. And once I did my first launch, it was a mommy and me collection. The launch did well. I won't say it did incredibly well. It did well, right? But there was still a ton of learnings because I had never produced a product before. So overseeing manufacturing, understanding cost negotiation, all of these are new lessons for me. I had more resources, but it didn't take away from lessons still being learned. And I remember sending a cold pitch email to Target off of those learnings of me saying, I created this brand, we're six months old. This is what I've delivered to the marketplace. This is a case study that I have built of our first campaign. These are the lessons that I've learned. This product deserves to be on your floor because there are moms who seek to shop with intentionality that you are not targeting. And give me an opportunity. Off of that cold pitch email, I was awarded 400 Target stores to go into. And that's how we started our first retail relationship. I remember starting when I sent that to them with a headline. And it was, was working really from the end backwards. The headline read, Oh Olivia debuts in Target for a magical Christmas collection. And that's exactly what happened, which was crazy in some ways, but I saw it. I was incredibly clear on the vision. And our first order, got our first PO with Target. It was 70,000 pieces that we were supposed to distribute to 400 targets. And it took us probably about nine months to work, to number one, pay for. and work on delivering that order to Target so it can hit the shelves for Christmas. That's amazing. I think that's a really good segue into something else I want to talk to you about. You are launching a book, Audacious, which we're very excited to read. I would love to pick your brain on how do you think about business expansion because a book is a new channel. How did you kind of think about that? You know, I've been, I don't know if it's because I'm now a mom of three, right? But I'm in constant thought around what legacy am I gonna leave? Have I done all of the things that I want to do, right? Like what's next for me? How do I envision this? And I have some end goals that I want to achieve, right? I want an exit, right? Like I want to be able to continue to build this brand to a $300 million. Like I have some really big goals, but there are some incredible lessons that I have learned. Some bathroom moment crying on the floor lessons. Some uncontrollably, I don't know how this happened. Some of the highest peaks. I mean, some things that have happened to me that I'm like, well, that actually really happened. I want to share and deliver to folks. The book is called Audacious. I want people to know that their career and their life can intersect to be their dream, right? And I am a testament of that. Not because I do it right, not because I've gotten it right, but because I have put some frameworks in place around vision, around vision casting, around craft. my story around delivering an incredible pitch that has nothing to do with me, but everything to do with the other brands that are a part. I want people to know that this exists. And after they do all of the things, I also want people to know that surrender is a part of the journey. That after you've done all that you can do, right, then you surrender to knowing that what's going to be is going to be for you. And so, I am incredibly excited about it. And to be honest, I got the book deal off of an ask. It was, can you introduce me to your book agent? I wanna see if there is a pathway for me. And the person was like, absolutely, absolutely. And I got the book deal this past summer. The processes went incredibly fast, but I'm so excited to deliver this book to the world. And for folks to know that all you gotta have is a little bit of audacity. That's all you need. And you gotta make the decision to take the action steps every single day to show up for yourself. Yeah, I can definitely see all of that coming through with you. I love how so many of your biggest projects have come about by you just asking. Just send Target an email, you just asked if you could publish a book and that's awesome. There's power in the ask. Yes, for sure. So a big part of what you do is community. It's also teaching others. I'm curious, as you've spoken to women entrepreneurs in your community, what are some mistakes that you see people making and how do you help them overcome them? I think that self doubt is the number one thing that I see from most people, whether they're a woman or a man, right? I think that self doubt is the thing that paralyzes all of us. But when you take control and you know that without a shadow of a doubt that you're able and you're capable, right? And you remove the self doubt. is how you begin to position yourself and anchor yourself to win. Winning is not this one singular moment that happens on the entrepreneurial journey. Winning is deciding to show up for yourself and then receiving every moment that comes along. I wish I could say like every day was, you know, filled with ice cream and sprinkles. It's not. But when I think about the landscape and the breadth of what I've experienced over the last seven years, have some incredible wins. I also have some losses. My losses are not from the space of failure that I regret. Instead, I believe that it's the thing that actually grounds this book more than anything. It's the failures that I can share with you so that you then know. Okay, this is how she overcame that, and I'm going through that experience right now. These are things I can apply to my own life so I don't have to take the road less traveled. Yeah, it sounds like mindset is a really big one, as you've said. I know we've also talked to you just a little more tactically about you've noticed that entrepreneurs in your community don't really understand the power of finances, managing them, business credit, stuff like that. I'm curious what your experiences are with those things and the advice that you give to others. before I started El Olivia, I bootstrapped everything with boss of a media until this day, never taking any type of financing on it, right? And so where I did all the right things, right? There's a way to leverage business credit in a very different and unique way. And so once you set up your Dunn's Bride Street and you do all of those things, right? Especially when you have an intense... P &L that you're carrying with a product business, right? Of cogs and different things like that. You began to explore different ways in to fund your business. The headlines make us believe that getting venture-backed funding is the sexiest, most glorious way to get funding. And I think that is such a myth. And I think that we should combat that headline by showcasing to folks that you can get lines of credit. You can get your own personal financing. You don't have to sell your complete, you know, sometimes life, soul, whatever, right? To create a unicorn business from the perspective of just this one way to finance, right? And so I'm excited to be able to share with folks like I got my first line of credit, SBA loan, by understanding what my business credit was. I got my first business line. business credit card, line of credit, by understanding that, right? Through the solutions of NAF and being able to say business credit actually is very essential and I'm not necessarily the part, like I'm not solely responsible in a manner in which my house is, right? Or whatever that looks like. So I just want people to understand that there are options available to them, right? And specifically, when we are thinking about managing your personal expenses and your business expenses and how they should be separate, right? And how you build that up for it to work towards you. Of course, I was being leveraged off the aspect of a PO, right? So I had this thing that I could say, I'm gonna get this in return back to me, right? But even from the perspective of just growing your business, right? It takes capital to grow your business. You can't do it without some sort of capital expenses, rather that's human capital, Rather that's you funding to develop it, right? And so I just, I love that you guys have the solutions available for folks. And specifically as women entrepreneurs are the number one entrepreneur in this country, right? And they're growing at a rapid speed every single day. We need to not just know how to build and start a business. We need to know how to fund our business in a way that's impactful and profitable for our business to continue to expand and grow. And I know so many incredible business owners. that have 20, 30, 40, $50 million businesses, but only think that the way for them to grow is through venture-backed right? And it's like, how do we really reshift that narrative and tell them a different story of how they access dollars that are available to them through building business credit? Yeah, because another big thing about that is it allows you to retain full ownership over your business. And that's really important to a lot of people. Exactly. I'm also kind of curious. You've talked to us about having routines, the importance of mindset. How do you work finances into your routine? Do you have a routine? I'd love to just get your tips. I have to like really dig deep inside of me when I'm meeting with my CFO to go through these line items. You know, I did that last week. Oh, I did it last week with them for the quarter. Oh, here we go again. But then after I did it, I'm like, here we go again. Like now. have the tools that I need to continue to go forth, right? The thing that you feel like is your deficit, the thing that you're so afraid of, the thing that you don't want to touch is the thing that you need to lean into at least once a week to flex your muscle on being good about that thing. For me, I always tell this to folks, especially folks who come from corporate environments that were broken. I say, find you an environment that that you will be able to build your confidence in, that in return will build more confidence in you. And you're like, man, actually I'm really good at this thing. Let me go volunteer and do this thing. I can do more of it, right? I think on the flip side of that, that works the same for me in finance, right? It's like, how do I go and find myself in spaces? Every single day I make myself check my bank account. I log in every single day. I need to know and see where my money is going, how much money I have. I need to be privy to that, right? I don't need to be out here living in La La Land on thinking it's all roses and butterflies, right? So that's one thing. Getting you a proper CFO, someone who can help you book keep your business and utilizing the right tools to do that. So you understand your cashflow, you understand the taxes and the implications. and what you need to pay for, and then understanding how you can leverage that from your business credit perspective. Yeah, and how did think about hiring the CFO? When was the right time for you to outsource that? For me, it was the right time when I was leveraging two businesses and I had added more things on my P &L that I wasn't necessarily comfortable navigating. When I started in housing inventory, it was like, I need someone to manage how my cogs are flowing and working as I'm working with retailers, as I'm waiting on payments. and balance sheets and different things like that that are further out than what I'm in taking from just like a sponsorship perspective was when I knew that it was time for me to bring that in. I think that if a lesson that I wish I would have brought it in sooner, right? I wish that I would have known that there are three things that you need when you're starting a business. You need someone to manage your finances to look at them. When you have finances to manage, you need an attorney on hand because things will happen and come up. You need to be able to lean in to someone who can advise you when you're making contract decisions. And then the third thing is that you need to know that you cannot build a loan. Either if you don't have a team, find you a community to be a part of that will help. motivate and encourage you on some of the hardest days. I wish I would have known that on day one of me starting my business. Yeah, I love that. This has been such a motivating and uplifting episode. I feel like there's just so much value in here for people. Thank you so much for coming on here and sharing all of your wisdom. my god, thank you guys so much for having me. I could talk about this stuff all day long. We love it. I think there's definitely going to be a want for more. Absolutely. Thank you so much. Yeah.