Authority Magazine
Published in

Authority Magazine

Marla Isackson of Ossa: Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life

In this second chapter in my life, I realized that I had the freedom to dream and create without having a blueprint of how things were supposed to be done. The creative process is very different as an entrepreneur versus as an employee. I was starting with a blank slate — and that empowered me to innovate and hone in on my interests and passions.

Many successful people reinvented themselves in a later period in their life. Jeff Bezos worked in Wall Street before he reinvented himself and started Amazon. Sara Blakely sold office supplies before she started Spanx. Dwayne “The Rock” Johnson was a WWE wrestler before he became a successful actor and filmmaker. Arnold Schwarzenegger went from a bodybuilder, to an actor to a Governor. McDonald’s founder Ray Croc was a milkshake-device salesman before starting the McDonalds franchise in his 50's.

How does one reinvent themselves? What hurdles have to be overcome to take life in a new direction? How do you overcome those challenges? How do you ignore the naysayers? How do you push through the paralyzing fear?

In this series called “Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life “ we are interviewing successful people who reinvented themselves in a second chapter in life, to share their story and help empower others.

As a part of this interview series, I had the pleasure of interviewing Marla Isackson.

Marla Isackson is a seasoned marketing executive with over 25 years’ experience creating innovative marketing campaigns for world-famous brands including Citibank, American Express, Barnes & Noble, and WebMD. A longtime passionate supporter of women’s initiatives, Marla is creating a new movement for women in podcasting. She is the founder of Ossa (, a podcast network and two-sided marketplace with over 1000 podcasts, connecting women-hosted podcasts and women-focused brands in order to increase the representation and influence of women’s voices worldwide.

Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

We moved to Long Island from Brooklyn when I was in 2nd grade. I was always pretty independent and I loved to ride my bike and explore my neighborhood. The town I lived in was very large and geographically spread out and included many cul de sacs, some with ponds, some on the banks of a larger bay. Spending hours on my bike, I remember thinking that I was a great explorer discovering new lands. My town had a really great shopping area and I loved to spend my weekends with friends walking around town, shopping and eating lunch at a neighborhood tearoom. When I was in middle school, my family moved to a different area of Long Island and I lived there through the end of high school. I was involved in a lot of extracurricular activities, including various service organizations. I also had multiple part-time jobs, like working at a neighborhood department store and a fashion boutique. It was always important to me to earn my own money. This helped to foster an even greater sense of independence within me.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

While I was developing an approach to help myself work through daily challenges in a positive mindset, I adopted the mantra “Everything is Figureoutable”.When confronting challenges or issues, I approach problem solving with this quote in mind. It’s a mantra that guides me as I work towards achieving clarity and resolution.

You have been blessed with much success. In your opinion, what are the top three qualities that you possess that have helped you accomplish so much? If you can, please share a story or example for each.

  1. I trust myself and my team, and it enables me to be very tenacious. I’ve always been the type of person who will do whatever it takes to achieve my goals. I approach decision-making with very careful consideration, but I trust my analytic process. I know that I can find strength in the lessons I’ve learned throughout my life, and I can trust my gut instinct to guide my decisions.
  2. I believe in the power of collaboration. Early on in my career, I realized that I could not and did not possess all the skills I needed to move my business forward, and that was okay. Working with dedicated colleagues with complementary skills toward a shared mission has enabled me to achieve success.
  3. I always try to lead with empathy and humility. I believe that these two qualities are key differentiators in the strength of many women leaders. Building thriving communities for women requires me to focus on the needs and desires of the women my communities are built to serve. I have to understand their hopes, dreams and desires in order to create a community ethos that supports our members. Our incredible community members inspire me every day. Getting to know them has been a profoundly meaningful and humbling experience for me.I am forever grateful to have the opportunity to nurture and support their endeavors.

Let’s now shift to the main part of our discussion about ‘Second Chapters’. Can you tell our readers about your career experience before your Second Chapter?

Before I started Like A Boss Girls (my first women’s community), I was a corporate marketing executive. I have over 25 years of experience creating innovative marketing campaigns for world-famous brands like Citibank, American Express, Barnes & Noble, andWebMD.

During my time at American Express, I managed a marketing budget of $200 million and led a team that generated over $2 billion in revenue. We developed the concept for the Blue Card and I led the consumer direct marketing launch. It was one of the most successful product launches to date for American Express. During the dot-com boom, I left American Express for a position at WebMD. I was SVP of Marketing during their initial launch period and worked on key brand amplification initiatives.

And how did you “reinvent yourself” in your Second Chapter?

As a corporate marketing executive, I was responsible for developing creative strategies and solutions that would work within the framework of an established business. Coming up with new and innovative programs and products was an important component of my job — but no matter how much I invested my heart and soul into my job, the things I worked on weren’t actually “mine”.

In this second chapter in my life, I realized that I had the freedom to dream and create without having a blueprint of how things were supposed to be done. The creative process is very different as an entrepreneur versus as an employee. I was starting with a blank slate — and that empowered me to innovate and hone in on my interests and passions.

When I thought about how I wanted to approach building my own business, I decided to focus my efforts on empowering young women to succeed in their careers. As a woman who had worked in senior positions at major corporations, I knew I could leverage my experiences to help other women. I wanted to use this knowledge to reinvent myself — so I created Like A Boss Girls.

Like A Boss Girls was a platform, resource, and community that I built for 8 years. It was a place where women would find support and advice while pursuing personal and career success — however they chose to define it. I wanted to create a home base for women entrepreneurs, social activists, leaders and go-getters — the type of resource that I wished I’d had access to in the early days of my career.

Fast forward to 2018. I had built a community of over 1.2 million, but I started to realize that we were all outgrowing the type of community I’d built. Society and culture had evolved, and the type of content that people were interested in consuming had started to trend in a new direction.

Like A Boss Girls had centered around our blog and Facebook, and that was no longer the best way to reach people. I brought on a new Editor-in-Chief, Meredith Reed, who encouraged me to “cut the cord” from some of our past content and to rebrand our platform in a way that would truly resonate with the present-day empowered woman.

I saw incredible potential in the future of the podcast industry. It felt like a huge leap at the time, but I decided to pivot my company from a women’s empowerment blog to a women’s podcast network. We took the Like a Boss Girls platform and transformed it into Ossa.

Can you tell us about the specific trigger that made you decide that you were going to “take the plunge” and make your huge transition?

There was a series of issues and events that led to my decision. I had grown tired of the office politics and living in the rigid corporate culture. I was becoming increasingly frustrated by having to go through multiple layers of management to get approvals for standard business initiatives and how it slows the speed of implementation. I was feeling drained and exhausted, and I don’t have the type of personality that allows me to conform to a culture if it just isn’t a good fit.

I decided to take the plunge and follow my heart. I wanted to dedicate myself to improving the lives of others, specifically women, who were looking to find their place in the world. I was proud to be the founder & CEO of Like A Boss Girls, and now I am proud to lead Ossa. Ossa is a podcast network and two-sided marketplace that connects women-hosted podcasts and women-focused brands. Our mission is to increase the representation and influence of women’s voices worldwide.

Our mission means a lot to me. I want to help women understand the true power of their voice. There is never a day that passes when I question my decision to leave my corporate career to become an entrepreneur. Being able to bring my vision to life and create something that matters to me every day is the most fulfilling and rewarding path I ever could have taken.

What did you do to discover that you had a new skill set inside of you that you haven’t been maximizing? How did you find that and how did you ultimately overcome the barriers to help manifest those powers?

I never thought I would be the CEO of a tech platform, but here I am! Building the Ossa network has pushed me to develop a far more sophisticated understanding of operations and technology. Since my prior professional experience centered around marketing and business strategy, I didn’t have much experience focusing on operational details. I did a lot of research, read everything I could find, and spoke with web developers and other technological experts.

How are things going with this new initiative? We would love to hear some specific examples or stories.

I truly feel that my company’s pivot into podcasting was the right decision at the right moment in time. In February 2018, there were about 500,000 shows on Apple Podcasts. Today, just two years later, we are approaching 2 million.

The podcasting boom is attracting a lot of attention in the world of digital advertising, which has been great for our ad booking platform. The podcast ad spend was $800 million in 2020 and is expected to more than double to $1.7 billion by 2024.

The podcast industry proved its resiliency during COVID, as one of the only forms of digital advertising that didn’t lose money in 2020. Podcast listenership grew, and podcasts became an important outlet for millions of people stuck at home during the pandemic.

Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

When I decided to make the transition from my corporate career to entrepreneurship, I created an informal advisory board of friends, family members, and colleagues. This board has helped me strategize and has supported me in so many ways while building a business.

I have participated in various mastermind groups over the years, and I find them to be extremely helpful. I love connecting with other women entrepreneurs and getting inspired in a supportive and interactive environment.

My business coach, Debra Angilletta, has been invaluable to me throughout my journey as an entrepreneur. She understands me so well. I appreciate that she knows how to work with my personality, match my working style, and keep me focused on my goals. Debra is incredibly smart and intuitive and challenges me every day.

Can you share the most interesting story that happened to you since you started in this new direction?

I spent a great deal of time thinking about my vision for Ossa before I decided to pivot my company from a women’s empowerment network into the world of podcasting. It was difficult to feel like I was letting go of the platform that I’d poured my heart into for so many years — but my intuition told me that it was the right decision.

Podcasts allow people to tell their stories and share their voice on a global scale. Women are underrepresented in the podcast industry, with only 27% of all podcasts hosted by women. I want to change this, because I know that podcasting can be used as a tool for empowerment.

Did you ever struggle with believing in yourself? If so, how did you overcome that limiting belief about yourself? Can you share a story or example?

I have high standards for myself, and I still experience periods of self-doubt. As an entrepreneur, some days are fabulous and I feel like I’m killing it. On other days, I question my abilities and feel like I’m not as successful as I’d like to be.

I’ve found that a huge part of building a successful career or a business is mindset. It’s all about reframing my thoughts to celebrate my wins. I have learned how to shift my focus from fixating on the problem to figuring out solutions when things go awry.

I remember one example of when I first discovered the power of mindset. It was during my corporate career, while I was a member of my division’s management team.

One day, we held an offsite meeting for all of the division members. I found out that I was going to need to get up and deliver a speech at the end of the day, distilling key points from the day’s presentations.

I was incredibly nervous about giving a speech in front of so many important people without having time to prepare. I remember doing an exercise where I envisioned myself delivering a successful presentation. I reframed my mindset and focused on the famous quote from Apollo 13 — “failure is not an option”. I made the decision to nail it — and I did.

In my own work I usually encourage my clients to ask for support before they embark on something new. How did you create your support system before you moved to your new chapter?

I created an Ossa advisory board, which consists of my business coach and 2 co founders of a digital strategy agency who help me figure out the best ways to grow Ossa as a business.

I also have a team of very talented women who have worked with me since the Like a Boss Girls era, and I have the support of my family and a few very close friends.

Before I transitioned my company, I thought about the type of support that I knew I would need, and then I asked for it. My motto is: “I’m only as good as the people I surround myself with”.

Starting a new chapter usually means getting out of your comfort zone, how did you do that? Can you share a story or example of that?

The transition from corporate executive to entrepreneur was not easy. Sometimes I missed the support and infrastructure that I had access to as an employee, even though it was that same structure that had made me want to strike out on my own. When you’re used to having access to a large support staff, technical resources, a huge marketing budget, a financial director, and an array of proprietary market research tools, it can be challenging to start your own company without any of those key resources.

When I first became an entrepreneur, it was an intense culture shock. I was bootstrapping my new venture, which limited the funds I had available to bring in external resources. It took me a long time to figure out how to execute technological and operational tasks that I would have previously assigned to a staff member.

As a corporate employee, my days were structured with meetings, calls, and updates. I had the typical rhythm of working in an office. When I started working from a home office, I had to create a new work day structure for myself. I found this to be very challenging.

Once I pivoted my company to Ossa, it created a new opportunity to push myself out of my comfort zone. Ossa incorporates much more technology than I’ve ever worked with before. I had to immerse myself in new technology in order to make effective decisions to build my company’s infrastructure.

One recent example is our recent launch of Ossa Insights. We created a platform on our network that provides our podcasters with a bird’s eye view of their analytics across every touchpoint of their business. This project required me to connect with many key podcast technology companies. I needed to know enough to be able to evaluate their capability to serve as a potential partner for this endeavor.

Fantastic. Here is the main question of our interview. What are your “5 things I wish someone told me before I started leading my organization” and why? Please share a story or example for each.

Here is my list of 5 things I wish someone told me before I started leading my organization

  1. Identify Your Why: Simon Sinek’s Ted Talk “Finding Your ‘Why’” had a significant impact on how I view my business. It helped me evaluate my motivation, purpose, and mission. It may seem pretty straightforward, but as an entrepreneur, it’s so important to know exactly WHY you’re getting up every day and building whatever it is that you’re building. When I was thinking about starting Ossa, I watched this video many, many times. Using this framework for thinking about my business has enabled me to make better decisions. Before I take on any new initiative for Ossa, I ask myself, “How does this support my company’s mission, goals and values? How will this initiative serve our community of women in podcasting?”
  2. Take action. As an entrepreneur, I don’t have the time or resources to obsess over every single detail. In order to foster innovation and facilitate the growth of my company, I need to take action. I’ve learned how important it is to have a process to quickly test and evaluate an initiative. You don’t need everything to be perfect the first time. Test the idea with your target audience, get feedback from them, tweak the concept as needed, and test it again. Using this process, I can identify winning projects early on, and eliminate others that won’t move the needle.
  3. Ask for help early in the process. Rather than adopting an attitude of “I can do it by myself”, I realized that I needed support. I looked to trusted friends, family, and professional colleagues and created my own advisory board. I’m able to consult my group of mentors on every major initiative or decision. This group is my sounding board and helps me to focus and stay on task.
  4. “If you build it, they won’t necessarily come”. I have slightly altered the famous line from the movie Field of Dreams for this one. Over time, I have realized the importance of being a public face for my brand. It doesn’t come naturally to me to put myself front and center, but I’ve learned that it’s an essential part of amplifying my brand. For many years, I wanted to stay behind the scenes and focus solely on building a great product. I assumed that would be enough for the right people to find us on their own. I have gradually come to realize that I can’t put in all of my energy behind the scenes. I also need to put myself out there and tell people about my company!
  5. “Everything is figuroutable”. I adopted this mantra from business expert Marie Forleo. Her philosophy has really helped me to solve problems more effectively. When you are building a company, things will go wrong. Systems will crash. A marketing campaign will turn out to be a total dud. I’ve learned how important it is to take a deep breath and remind myself that the crisis of the moment is really not as big as it seems. Identifying the root of the problem, isolating the issues, and formulating solutions are the important next steps. I would compare this to the process of baking. I love to bake, and when you’re baking at an amateur level, you need to follow a recipe. I take the same approach to solving problems in my business. I work with my team to figure out our problem-solving recipe — a step-by-step approach that will allow us to tackle the issue and keep moving forward.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

Ossa’s mission is purpose-driven — to increase the visibility, influence and earning power of women in the podcast industry. I would love to be able to expand our reach and amplify the voices of women in underrepresented communities on a global scale. Podcasting is a very powerful medium. Compared to most other forms of digital media, it has a low barrier to entry for production and implementation. I want to continue to empower women and show them that their voice has value.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them. :-)

I would really appreciate the opportunity to connect with Arianna Huffington. I admire her and I am inspired as to how she continues to take risks and reinvent herself, creating transformational initiatives and businesses touching the lives of many.

How can our readers further follow your work online? ;

Thank you so much for sharing these important insights. We wish you continued success and good health!




In-depth Interviews with Authorities in Business, Pop Culture, Wellness, Social Impact, and Tech. We use interviews to draw out stories that are both empowering and actionable.

Recommended from Medium

True Life: Our Latest Bootcamp Class is 50% Women.

Top Courses on

How every decision you make is wrong

Workplace flexibility… 3 ways to do it right

Week 58 — Welcoming DayOne’s Newest Member

What I Learnt From 3 Years Of Working In Production Support

Show Up and Do the Work

My Memoirs of My Management Consulting Practice.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
Pirie Jones Grossman

Pirie Jones Grossman

TedX Speaker, Influencer, Bestselling Author and former TV host for E! Entertainment Television, Fox Television, NBC, CBS and ABC.

More from Medium

Self Made Women: Celeste Durve and Kelsi Kitchner Of VIPER On How They Started With Nothing and…

Get those Credit card/loan debts off your report ASAP

Now Is the Best Time to….

Cassandra Hudson Of EngageSmart: 5 Things I Wish Someone Told Me Before I Became a C-Suite…