In Episode 20 of DissedMedia: A Startup Story, founder of DissedMedia, Ben Olmos, offers listeners a transparent look at the struggles and revelations he’s encountered over the past year. From grappling with personal loss to reimagining his goals for DissedMedia, Ben shares his journey of building a business podcast and trying to grow an audience while balancing life’s challenges. This episode dives deep into resilience, content strategy, and the realities of building a media platform from the ground up.

1. Facing Personal and Professional Setbacks
Early in the episode, Ben discusses the impact of losing his father, which brought production to a near halt. Additionally, he lost podcast co-host, Alan, who had been a great collaborator and contributor for the business podcast and The Daily Pitch. These changes weighed heavily on Ben, leading him to question his path forward. However, his story is a testament to the strength required to pick up the pieces and keep pushing forward, even when motivation fades.
2. Reevaluating the Content Strategy for a Niche Audience
Before these setbacks, Ben was experimenting with SEO, social media content, and even an e-learning platform for The Daily Pitch. Although his initial efforts laid a strong foundation, he realized the need for more consistent and audience-focused content strategy. In this episode, Ben shares his shift towards creating “evergreen” content, material that remains valuable over time, allowing him to maximize audience engagement even during slower periods. This focus on content strategy has become a cornerstone for keeping DissedMedia relevant and impactful.
3. Supporting Experts Through DissedMedia
Ben’s vision for DissedMedia extends beyond traditional media; he aims to create a platform where industry experts and thought leaders can share insights and reach new audiences. In Episode 20, he highlights how DissedMedia supports these professionals by distributing their content across various channels, including social media and newsletters. This approach not only enhances DissedMedia’s reach but also strengthens its content strategy by adding diverse perspectives and topics that appeal to its niche audience.
4. The Growth of a Vertically Integrated Content Platform
Over time, Ben has transformed DissedMedia into more than just a media site. Through thoughtful integration of e-learning, e-commerce, AdSense, and content publication, he has crafted what he describes as a “vertically integrated bouquet” of services. This comprehensive approach supports a dynamic content strategy, allowing DissedMedia to meet a variety of audience needs, from education to accessible, expert insights, while positioning the platform for future growth.
5. Realigning Goals and Expectations
Ben is realistic about the challenges of building an audience within the business and leadership niche, which often has slower growth compared to more mainstream content areas. He has adjusted his expectations accordingly, understanding that success in a niche market demands time and commitment. This long-term approach underscores the importance of a patient and evolving content strategy that aligns with audience needs and interests.
6. Looking to the Future with Renewed Dedication
Despite obstacles and slow revenue growth, Ben remains optimistic about DissedMedia’s future. He reiterates his commitment to the platform’s mission: to help managers, leaders, and entrepreneurs improve through quality content and expert insights. With a renewed sense of purpose, he promises to continue refining his content strategy, exploring new engagement methods, and staying connected with his audience.
Key Lessons for Entrepreneurs from Episode 20
- Persistence is essential: Personal and professional challenges can disrupt progress, but resilience is critical to moving forward.
- Consistency builds trust: Regular, high-quality content, especially in niche markets, can help grow an engaged audience.
- Adaptability is key: Ben’s focus on evergreen content reflects the need for a flexible content strategy that can adapt to real-world conditions.
- Nurture your audience: Growing a dedicated following takes time, particularly in specialized areas like business and leadership.
- Create a multi-channel approach: A dynamic content strategy leverages multiple channels to reach and engage diverse audience segments.
In Episode 20, Ben’s reflections underscore the complexities of launching and sustaining a business podcast. Through his experiences, listeners gain a clear understanding of the dedication required to turn passion into a viable venture. DissedMedia’s journey reminds entrepreneurs that while the road may be tough, adaptability, focus, and commitment are essential for success.