Marla Isackson is the founder of the OSSA Collective and host of the Mind of a Mentor podcast. A former marketing executive for corporations like American Express, WebMD and Barnes and Noble, Marla formed Like a Boss Girls in 2004. The website was created for and about women to help and inspire them to make a living, make a difference, and make it big. In 2018, Marla rebranded her site as Ossa, a podcast network for female thought leaders dedicated to promoting social progress through the oldest form of communication and storytelling: the spoken word.

Learn more about Marla and OSSA.

Learn more about The Passionistas Project.


Passionistas: Hi and welcome to The Passionistas Project Podcast. We're Amy and Nancy Harrington and today we're talking with Marla Isackson. A former marketing executive for corporations like American express, WebMD and Barnes and Noble, Marla formed Like a Boss Girls in 2004. The website was created for and about women to help inspire them to make a living, make a difference and make it big.

In 2018 Marla rebranded her site as Ossa, a podcast network for female thought leaders dedicated to promoting social progress through the oldest form of communication and storytelling — the spoken word.

So please welcome to the show, Marla Isackson.

Marla: Thank you so much for having me today. I'm really excited to be on. I really appreciate it.

Passionistas: Marla, what's the one thing you're most passionate about?

Marla: utting family aside, 'cause I'm most passionate about that. I would say that I'm really passionate about what I'm doing because I really feel that our mission with Ossa or my mission, I should say, is to really help elevate the voices of women. And I've been working at this for a long time, both with Like a Boss Girls and us. The bottom line, I want to make sure women really do have a seat at the table. That's so important to me.

Passionistas: Why?

Marla: Because we have a lot to say. I've been in a situation where I've been invited to the table, but then I'm been ignored through the process of developing Like a Boss Girls and Ossa. I've worked with some incredible women. I've met incredible women and I'm just impressed with how much value they can add to the conversation. So that's why I think it's important for women to be at the table and to be encouraged to contribute. We have a lot to offer. I've had the opportunity to work with some incredible women in my corporate life as well as with Like a Boss Girls and with Ossa I have learned and experienced that women have a tremendous amount of value to add and for women not to be having a seat at the table. It's an incomplete conversation.

Passionistas: Let's take a step back and you started your career in marketing, so tell us about that and some of the challenges you had working with these big corporations.

Marla: I'll take a step further back, which is I first started my life in retailing working for a department store that's not in existence anymore called Abraham and Straus. I learned a lot about the customer at that point. After two years I realized I could leverage that experience and knowledge and start my marketing career. So I've had the opportunity to work for a big company such as Citibank and American express, Barnes and noble and Web MD. And I honestly thought they were incredible opportunities. I felt very grateful. I worked hard. I learned a lot. I am who I am now because of the experiences I had working at these companies. I learned I, it was incredible on the job training. I have to say that and I loved meeting really cool people from different walks of life. It was a great experience. I can't deny it. I'm very, very glad that I had the opportunity to do so.

Passionistas: Talk a little bit about the challenges you faced being a woman with a lot of male colleagues.

Marla: I worked in corporate America during the time when there was a lot of conversation about the glass ceiling. So for example, not to date myself, but when I started working for the bank, I mean people walked around with a little bow ties what women did. So it was just a different world then. It's not that people were overtly hostile to women, but we felt very snubbed. And that was part of the issue. I think things began to change when more and more women were promoted into areas of importance. And then women were encouraged to speak at the table. But I will tell you that, you know, I definitely experienced times in these big companies where we'd be in a big conference and there'd be a lot of people around and I would say something and I would get ignored.

And then a guy would say the same thing and they would be like, Oh my gosh, what a wonderful idea. And that used to irritate me and it didn't just happen to me. It happened to a lot of women. And you know, I remember talking about it with some colleagues and we just were not sure how to crack the code. I mean, we tried different, you know, you know, standing up or speaking with a different tone and voice, but it didn't matter. So we weren't able to crack that code. But I absolutely experienced that situation on a number of occasions. It was really depressing. And I made me so angry because it really took away the value of that. I thought that I was adding to the conversation as well as to the company and that was a problem. There were situations where there are a couple of senior execs, males who, I don't know, maybe a little, we're a little more enlightened, pay attention to it a little bit more.

So I would say something, a guy would say something the same thing I said and, but then the executive would come back to me asking to clarify and add to my point. So you know, I started to see the change, but there were still a lot of situations where that was a problem. You know, there's still a lot of situations where male executives, they'd go golfing and you know, not to say women don't golf, but a lot of us didn't golf. A lot of businesses held when the golf course. So I'm hoping that the generation of today that women are playing golf because that's super important. But it really is a metaphor illustrating the fact that I still felt different. I was the other person. I wasn't one of the crew, I don't even say one of the guys, but I didn't feel like I was one of the gang when we had conversations like this.

Also, many of the senior executives had wives that worked. So I will never forget having the conversation with the senior executive who said, don't worry about it, Marla, you know, your husband makes a lot of money. You know, when, when I was talking about a particular promotion, yeah, that's okay. You know, you'll be, you'll be okay. But he really needs the money. So I'm hoping those kinds of conversations don't still happen, but I will never forget that conversation. I didn't even know it. How do you respond to that? I didn't even know what to say. I was stunned, absolutely stunned. There was situations where I would be, you know, I was hired. This was not a titty bank or American express. And I find out that people working for me, older guys were making more money than I was making. So this stuff went on a lot.

And again, I haven't worked for a big company in a long time, but I certainly hope that there have been some changes that have been made.

Passionistas: Why did you decide to strike out on your own and what was your first project?

Marla: Basically I had great experiences, so the big corporations were incredible just based on the projects I've worked on and the people I managed, the huge marketing budgets that I had. I ended up working for a startup, so I had a bit of that taste of startup and then I worked for a smaller company and I will tell you that honestly I got really exhausted. It was very tiring. I felt like I was consistently having to parrot what they wanted me to say. I didn't feel like I was in control because I wasn't because it wasn't my company. I would certainly voice my opinion when we discussed strategy, but I was not the ultimate decision maker.

And that got me super frustrated and it got to a point where in addition to just feeling kind of exhausted, I also wanted be in a situation where I was affecting the outcome and I was focusing on a project that I felt really passionate about. Not that I didn't love my jobs, I certainly did love them, but I felt it was really time to take that next step and really focus on things that really sing to me.

Passionistas: Tell us about founding Heart of Gold Girls and why you wanted to work with teens specifically.

Marla: That was my first foray into having my own company and I decided to focus on the teen market cause my daughter was a teenager at the time and I really felt that teen girls were not being served the way they should. And this was like very early days internet. So a lot of stuff that teen girls were exposed to was a lot of stuff about celebrities and how to please your man and all this other nonsense.

But I didn't see that there was a whole lot of conversations focusing on really developing as a woman and following your passion and making an impact in the world. So that was quite a number of years ago and I wanted to do something about that. So that's why I founded Heart of Gold Girls and it was a content social media site as well. And we did that for about two years or so. I had a small team of people and then after a while I felt that I could not serve teen girls the way I wanted to serve them. I think, you know, obviously I'm much older and my daughter was not a teen anymore and I just felt like I wasn't close enough to the customer and that made me uncomfortable. So we repositioned to Like a Boss Girls and we were like really the first boss girl thing.

And then all of a sudden afterwards, like everyone is a girl boss, a boss, girl, a boss, babe, whatnot. But basically what I wanted to do was to help women starting out. So either leaving high school or college or postgraduate. I know, again, this is really based on the experiences of my daughter and son. That's a really hard transition to make. It may not be the first time that you're living on your own because a lot of people do go to college, but it's the time that you're really an adult and you have to make some decisions that maybe in the past your parents would make for you. And I felt that that was important and I wanted to create structure. I wanted to create content that would be useful to this population that would really help them make the transition more effectively so that they actually could get to where they wanted to be.

So again, it was a content site and focused on getting a job, money, health and wellness relationships. We covered a whole bunch of different verticals, again, with the mindset of women just starting out in the world who maybe need a little support. The other reason why I did this, again, I'm a like a research nerd and I remember reading a lot of research that when people graduate from college, they often move to towns or cities and they're not from that area and there's a lot of loneliness and not a whole lot of connection. And again, it was as the internet was kicking in, we felt that there was an opportunity to use all these tools to help women feel more connected with each other. And that was another goal.

Passionistas: At what point in your journey did you decide to get into podcasting and why did you do that?

Marla: It was the beginning of 2018 and in a strategy session with my team and we were talking about ways to amplify Like a Boss Girls amplify the brand, extend the brand, have a touch more people. And my team suggested very strongly that I start a podcast, which I really didn't want to do, but I did. And we call it Mind of a Mentor. And again, the structure is about, it does talk about mentoring, but the woman being interviewed is actually the mentor. So essentially she's taking us through her heroic journey, which we all have and talking about challenges, issues, obstacles that they encountered along the way and how they did or did not deal with these issues. So I thought it was a great platform. I would say my first few episodes were horrendous because I was petrified. But then as I got into it, I really enjoyed the medium a lot.

I just said, well this is just a really, really cool, I like the fact that I'm getting to speak with a lot of very interesting women cause Mind of a Mentor does focus on women and it just was really liking the medium. And then I did more research to learn more about podcasting and based on the research, lo and behold, huge opportunity growing channel also found out that women were not monetizing to the level that men were monetizing when it came to podcasting. I think men were involved with podcasting a lot earlier on, so they tended to have the bigger podcasts. And I felt that podcasting was a natural medium for women because I think you can get into both the emotional issues as well as the more practical issues when two women are having a conversation. So did my research, saw that there was an opportunity and decided to take mine to have a mentor to take the concept of podcasting and actually go the next step, which is creating the Ossa platform.

Passionistas: So before we get to Ossa, so tell us a little bit more about the podcast. What types of women do you interview and what have you learned from them?

Marla: I would say that I've interviewed, oh my gosh, all kinds of women. I've interviewed athletes. I've interviewed women in transition, women who have had abusive relationships, women who had seriously horrible childhood. Bottom line is they're all professional women. They all have jobs, they run a business, they have a career. But they've all gone through some really serious issues along the way. And I felt that these stories were really interesting. They're very, very helpful because what they've gone through is not unusual. So there are many women unfortunately who have been in these kinds of situations. So the objective is for someone listening to Mind of a Mentor to be able to say, well, you know, if she could do it then I can do it. And that's the framework.

Passionistas: We're Amy and Nancy Harrington and you're listening to The Passionistas Project Podcast and our interview with Marla Isackson. To learn more about her podcast network for female thought leaders, visit Now here's more of our interview with Marla.

Passionistas: Tell us more about Ossa and the mission and how it works for both the podcast or and the advertiser.

Marla: In my mind, the best way to help women accomplish and achieve their goals. A lot of it has to do with financial goals. So you've got to make money. Making money is really important. Having that career is really important. And again, going back to the research and looking at the difference in monetization, I saw that there was a really big gap, which just did not seem right to me. So well the overall objective is really to help women podcasters monetize their podcast and extend their voice.

But we actually are a matching platform, which is very similar to when you go online to select a flight. You put in your criteria and up pops the flights that match your criteria. Ossa is a matching site, so we work with brands, they can leverage the platform, put in their respective criteria, and up pops the podcast that meet that criteria. So we make the match. So we're helping brands make more money reach women that they may not have reached before because of the opportunity to speak to a very targeted group of women in these podcasts. And we're also working with women who love podcasting, but maybe had not cracked the code on how to make money. So that was really the objective.

Passionistas: How do you help smaller podcasters grow their audience and appeal to advertisers?

Marla: Basically? We've done a couple of things. Most recently we launched an eCourse called grow your show and it's a really cool, I love it because we had subject matter experts in our community create each module.

So it's a very like organic kind of course, which is you go on, you take each module, you learn tips, tools, resources in terms of what to do to increase your numbers. But you're hearing from women who have gone through very similar experiences and they bring their own flavor to the conversation. So that's something we're very proud of. We just launched that very recently. So that's one thing. When you become a podcast or on Ossa, you can join our private Facebook group and on Ossa, various online guests, webinars, we record the calls, they're on various topics relating to podcasting and we'd push it out to our members are also podcast members. We have an Ossa special Ossa newsletter for our members where we talk about opportunities, new findings. We will bring in, if there's some news in the podcasting world, we'll connect that information. The other thing we do is, you know, getting back to sort of podcasting news on our content site, which we still have, which is pivoted more towards podcasting.

We try to use it as a tool to make podcasts are smarter about podcasting. So my point is the more information tools and resources we can put in a Podcaster's hands, we feel that hopefully they will use that information to actually focus on growing their numbers. And we're constantly thinking of other new opportunities to help our podcast or community cause it's super important to us.

Passionistas: And is there something that you personally have learned as a podcaster from all of these resources?

Marla: I think a couple of things. The first is that everyone has a story and it doesn't have to be dramatic. You don't have to be the most famous person in the world. But every woman, everyone has a story. And the wisdom that's conveyed during these conversations is remarkable about all different facets of life, work, relationships, parents, etcetera. So I'm enjoying the richness of these conversations and I didn't quite think that that would be the situation.

I don't know what I was expecting, but I didn't quite expect this. So that's a big thing. I have enjoyed meeting just overall some amazing woman that I would not have met in the past. So having the podcast has enabled me to reach out and go beyond my job function and connect with women that there's not a chance that I ever would have met them before and it's made my life richer. So I've enjoyed that.

Passionistas: So do you ever feel unmotivated and if you do, how do you get past it?

Marla: I'm sure many of us have seen the cartoons that show the life of an entrepreneur, which one day you're up, one day you're down. When you're up, one day you're down. And I feel that way. So the thing is that I'm like other entrepreneurs inpatient, I'm wanting things to happen faster than they're happening.

I get cranky when I realized that I could maybe move faster if I had more investment dollars. So these are things that can get to me after a time that can make me wake up and say, Oh, what am I doing? Like really, what am I doing? But then I get on a conversation with my team and I get jazzed again because I see the opportunity. So look, it's really hard to sustain that level of energy every day. And there are ups and downs, but I think what I really try to do is think of my overall goal and just try to be a little more patient, which is not easy, not easy.

Passionistas: Do you have a character trait that you think really helps you keep going?

Marla: I am a bit of a perfectionist, which can be good or bad, but I use the perfectionism as I know something should get done.

It would be great if it would get done. So I make it happen and that process leads to me enhancing my business. So that sort of impatience is, as I said, good and bad. I'm very curious. So I'm on the computer a lot. We have to be careful because that could be the big black hole, but I'm constantly doing research about topics relating to podcasting or the economy because I want to be smarter and I want more knowledge that I can create strategies that will be even more impactful. So I think it's important to be curious and I am super curious. One of the reasons why I enjoy podcasting so much or the act of being a podcast host is that I'm very curious and it gives me an opportunity to ask a whole lot of questions that probably would not be polite for me to ask in any other venue.

But because you're having a conversation on a podcast, I'm free to ask whatever question I want. So I enjoy that. So I think curiosity is probably a really big piece of who I am.

Passionistas: Do you find now that you are asking people questions on the podcast, do you carry that over more into your social personality?

Marla: I think what I've learned from podcasting is to pay more attention. So, for example, with my end of a mentor, I asked women to start in their early days because I'm always trying to listen for themes and threads that I can pull in to the latter part of the conversation. So when a woman is talking about what she's doing now, obviously most cases there's a huge correlation to the way they were as a young girl and their focus and their interests now. So that's kind of what I try to do.

I don't know if it extends to my personal life, but I guess overall I try to be a better listener, let's put it that way. I really do. I think that's an important point. I think it's taught me to be a more patient listener.

Passionistas: Looking back on your whole journey so far, do you think that there was one decision that you consider your most courageous and that sort of changed the trajectory of your path?

Marla: I think there were a couple of key points, but I will tell you that in the summer, because this is a fairly recent experience, I was at one of the major podcast conferences and I started to talk about Ossa in a way that I don't know why I hadn't talked about also this way before I elevated the conversation. I talked about Ossa in a much bigger way and I realized that that was a huge turning point because I actually believe that Ossa can be what I was saying.

It could be more specifically. I decided to go all in and that was a really big decision and that was really a result of this conference I went to, which was like, am I going to make it or not? If I wanna really achieve what I'm saying I want to achieve, I gotta be all in and be super passionate about what I'm doing. That was important. That was just the summer actually. That was a very important turning point for me.

Passionistas: So what's your secret to a rewarding life?

Marla: I think it's a couple of things. Number one, it's just taking a step back and just counting my blessings. It's gratitude. You know, life is not easy. There are ups and downs, but I think for me it's always been important for me to say, wow, I am very grateful. I am grateful that I am where I am, that I have such a great family, that I've been able to build a career. I'd never take anything for granted. So I think it's really a lot has to do with gratitude.

Passionistas: Is there a mantra that you live by?

Marla: Yes. And now my team lives by it. So there's a great digital marketing person who's, I think she's amazing. Her name is Marie Forleo. She's very popular. She does these awesome courses and her mantra is everything is figureoutable. And that's, I've adopted that as my mantra. So so many times my team members, maybe they're flipping out about something, they're worried about something and I'm like, chill, everything is figureoutable. We'll figure it out. No one's dying over this. There is a solution. So to me that has gotten me through some really hairy experiences.

Passionistas: What's your definition of success?

Marla: It's two things. It's being able to really touch a lot of women, cause Ossa is a passion project for me. Yeah, I want to make money, but, but there's a passion and a purpose for what I'm doing.

Also being able to say that I've really was able to help women elevate their voices and expand their podcasts and help them make money. That's super important. And in turn, honestly, me being able to make money is very helpful as well. I mean, I'm not a nonprofit, so the fact that I can earn money doing something that I'm so passionate about that I believe is mission driven to me is a win-win. That's my definition of success.

Passionistas: Thanks for listening to The Passionistas Project Podcast and our interview with Marla Isackson. To learn more about her podcast network for female thought leaders, visit

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