The Rise and Fall of Digital Media Startups: The Case of Cheddar and the Changing Landscape
Hatched by Christian Riedi
Oct 20, 2025
3 min read
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The Rise and Fall of Digital Media Startups: The Case of Cheddar and the Changing Landscape
In recent years, the media landscape has witnessed a significant transformation, largely driven by the rise of digital platforms and the insatiable demand for on-the-go content. One of the most notable companies in this space was Cheddar, often dubbed the "CNBC for Millennials." Founded by Jon Steinberg, a former executive at BuzzFeed, Cheddar aimed to revolutionize how financial news was delivered, making it accessible, engaging, and tailored for a younger audience. However, the ambitious vision of Cheddar came with its challenges, eventually leading to a period of furloughs and restructuring. This narrative reflects broader trends within the digital media landscape that warrant exploration.
Cheddar launched with a clear mission: to provide financial news in a format that resonates with a younger demographic. Its programming spanned various engaging formats, including "Stretching Your Dollar," a daily live show from the New York Stock Exchange, and "Ready 4 Work," a docuseries that chronicled the journeys of job seekers navigating an ever-changing economy. This innovative approach was designed to capture a generation that consumes information differently, often preferring bite-sized, visually appealing content over traditional news formats.
One of Cheddar's most significant achievements came in 2018 when it reported on AT&T's acquisition of the online advertising company AppNexus for approximately $2 billion. This scoop not only cemented Cheddar’s reputation as a credible news source but also showcased the potential of digital media companies to break significant stories traditionally dominated by legacy news outlets. The acquisition of Cheddar by Altice USA for around $200 million in 2019 was a testament to the value that these innovative media startups could offer.
However, the narrative of Cheddar is not unique. It reflects a broader trend of digital media companies grappling with sustainability in an ever-competitive environment. As advertising revenues fluctuate and subscription models face challenges, many startups have struggled to find their footing. The notion that digital media could disrupt traditional outlets has been met with the harsh reality of economic pressures, shifting audience preferences, and the challenge of monetizing digital content effectively.
As the digital media landscape continues to evolve, several actionable strategies can be considered for startups looking to thrive in this competitive space:
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Diversify Revenue Streams: Relying solely on advertising can be risky. Startups should explore various monetization strategies, such as subscription models, sponsored content, and partnerships, to create a more resilient business model.
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Focus on Audience Engagement: Understanding the audience is crucial. Startups should invest in analytics to gather insights on viewer preferences and behavior, allowing them to tailor content that resonates and fosters loyalty.
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Embrace Agility in Content Creation: The ability to pivot and adapt to changing trends is essential. Startups should remain flexible in their content strategies, experimenting with different formats and platforms to stay relevant and capture audience attention.
In conclusion, Cheddar's journey underscores the complexities of navigating the digital media landscape. While it achieved remarkable milestones, it also faced significant challenges that many startups encounter. As the industry continues to evolve, those who can adapt to changing market dynamics, understand audience needs, and innovate in their approaches will be better positioned to succeed in the competitive arena of digital media.
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