Sam Yagan, a renowned serial entrepreneur known for co-founding SparkNotes, OkCupid, and Corazon Capital, commenced his enterprise journey in the 1990s with partners Max Krohn, Chris Coyne, and Eli Bolotin.
Yagan’s first venture, SparkNotes, became a popular study guide source for students, was later acquired by Barnes & Noble. His next project, OkCupid, revolutionized the online dating sector. His venture capital firm, Corazon Capital, assists early-stage tech start-ups through investments.
The team recognized the untapped potential for digitalizing traditional Cliff Notes. The concept swiftly gained traction leading to acquisition offers within a mere seven months. This success, however, was short-lived due to their parent company’s plummeting stock price, and they found themselves back on the selling block.
Despite enjoying the perks of being a millionaire during the dot-com bubble, Yagan experienced firsthand the turbulence of the tech industry. The drastic swings in fortune highlighted the unstable nature of this sector.
Fast forward to present day, Yagan who is a Chicago based venture capitalist, reveals regret over selling SparkNotes. He remembers the eagerness to sell SparkNotes to iTurf, an on-the-verge-of-bankruptcy internet company, for $30 million. When iTurf collapsed, the remaining debt fell on Yagan solidifying his remorse over the sale.
Years later, Yagan looks back at this episode as a valuable lesson in business judgement. He now ensures that the companies he invests in have a sustainable vision and plan.
Yagan admits that during the stock market crash, he failed to recognize the lasting impact of the internet. He ruminates that if they had retained SparkNotes, it could have served as an introduction to OkCupid for countless users, possibly even launching a new service named SparkMatch.
Today, Yagan advises other entrepreneurs, emphasizing the importance of adhering to core values and not overly succumbing to market trends. His advice stems from his personal experiences and a belief in the strength of established business principles regardless of fluctuating market dynamics.
