On May 5, 2025, Skype’s once-dominant video messaging service went dark after more than two decades – although it is still accessible for business users via Microsoft Teams.
For this week’s “Eye on Small – and not so small – Business,” the Westfair Business Journal checked in with Jason Kocina, president of the digital marketing and design company Checkerboard. In a blog he called “The Cautionary Tale of Skype’s Rise and Fall,” and originally published a week after Skype’s demise, Kocina reflected on the ultimate failure of a company that had not only become a household name but was also enshrined – temporarily – in the language as an English verb, giving his advice on how businesses can avoid going down the same path.
In the blog, which he gave us permission to quote, Kocina – who is based in Minnesota but whose message is valuable for businesses everywhere, and nowhere more so than business-orientated Westchester and Fairfield counties – emphasized the importance of maintaining brand visibility in an ever-evolving marketplace.
Sharing a series of strategic recommendations designed to help businesses stay afloat and flourish, Kocina first advised companies to ensure they are present wherever their customers seek information or recommendations.
“The way to avoid Skype’s fate is to proactively maintain a strong presence wherever your customers are searching.
Many businesses react to uncertain times by playing it safe and cutting back on marketing. But Kocina cautioned: “That only makes them less visible. Competitors who boldly remain present will capture all the interest.”
Indeed, research shows companies that keep up their marketing during economic downturns often emerge stronger and more competitive. The proof? Despite a challenging economy, the world’s 500 most valuable brands grew their value by 10% in 2024, according to a report by the California-based CMO Council.

Moreover, Kocina stressed the necessity of going beyond mere search engine optimization (SEO), which has become a touchstone for so many businesses, large and small, but is not the be-all-and-end-all of successful online trading.
“It’s not sufficient to just focus on SEO and an optimized website. SEO must be paired with steady, high-quality content and outreach. (And) being findable on Google and AI is an essential piece of the puzzle.”
Building a multichannel presence is another critical strategy that Kocina highlighted. He said he encourages brands to cultivate familiarity and trust by being consistently visible across various platforms.
These include earned media, namely positive press coverage and expert interviews, both of which can keep a brand top of mind and enhance its credibility. Another is owned content, in which brands can give followers a reason to stay engaged by sharing industry insights, success stories and valuable tips on their websites and social media. And a third is direct communication, such as email marketing, which Kocina said remains a powerful tool for maintaining a direct line with customers. He also noted that regular newsletters are effective in nurturing relationships and driving repeat engagement.
Consistency is key, according to Kocina, who added that it is not enough to implement a few strategies sporadically.
“Presenting a unified message everywhere will encourage people to recognize and trust you, making your brand familiar and credible.”
In closing, Kocina warned against complacency and urged businesses to act decisively.
“You have an opportunity right now to ensure your company’s story is one of success, not a cautionary tale. Tell your story while people are listening and looking for solutions, and before it’s too late to make an impact.
“Be the brand that thrives on this change – not one that fades away. Now is the time to step up, stand out and let your story shine.”












