What Color Is Your Parachute?

In the early 1970s, Tom Freston wasn't dreaming of media domination; he was just a guy who couldn't stomach selling Charmin toilet paper. After quitting his advertising job in a fit of existential dread, Freston embarked on a journey across the Sahara Desert that eventually led him to India and Afghanistan. By his mid-twenties, he had built a clothing import business that generated millions on paper, making him a young success in a world far removed from Manhattan boardrooms. However, the volatility of global politics and a trade embargo by Jimmy%20Carter brought the house down. At 33, Freston found himself back in New York, bankrupt and deep in debt, clutching a copy of What%20Color%20Is%20Your%20Parachute? that would pivot his life toward a nascent technology: cable television. The narrowcast revolution and the birth of MTV When MTV launched in 1981, the broadcast giants—ABC, NBC, and CBS—held a 95% market share. They viewed the startup as a joke, but Freston and a small team of seven others, backed by a joint venture between American%20Express and Warner%20Communications, were betting on a concept called "narrowcasting." Instead of being everything to everyone, they would be one thing to one specific person: the music-obsessed youth. They weren't building a channel of shows; they were building a "place" where the brand itself was the star. The business model was a triple threat: subscriber fees from cable operators, advertising revenue, and eventually, a massive consumer products engine fueled by intellectual property. This wasn't an easy win. In the beginning, the team struggled with cable operators who thought rock and roll was the work of the devil. Freston, leveraging his marketing background, had to prove demand in microcosms like Tulsa, Oklahoma, where residents went wild for 24-hour music videos. At its launch, the network only had 160 videos, mostly from the UK because American labels hadn't yet realized that visual storytelling could move LPs. But as artists like Madonna and Bruce%20Springsteen embraced the medium, the high-margin money machine began to hum, eventually scaling to $9 billion in revenue. Hiring aberrant talent to capture the cultural zeitgeist Freston’s secret sauce for disruption wasn't just the technology; it was a radical approach to talent. He consciously built an eccentric culture with a dress code famously described as "no frontal nudity." To stay ahead of the curve, he avoided hiring traditional media executives, instead filling the ranks with young, "aberrant" people—the ones who sat in the back of the class and had zero respect for the system. This strategy led to the discovery of creators like Mike%20Judge, whose short film "Frog Baseball" was greenlit in a minute and evolved into the phenomenon of Beavis%20and%20Butt-Head. Freston realized that to capture a 24-year-old audience, he needed to empower 24-year-olds to make the decisions. This philosophy extended to Nickelodeon, which became the most profitable arm of the business. Unlike Disney, which focused on "toyability," Freston’s team focused on character and irreverence. Shows like SpongeBob%20SquarePants and Rugrats weren't designed to be consumer product bonanzas from day one; they were simply shows the team loved. By putting creative people in charge of the networks and shielding them from the corporate "synergy" demands of parent company Viacom, Freston created a talent magnet that dominated the cultural landscape for decades. The billion dollar Facebook bid and the MySpace disaster By 2005, the digital revolution was beginning to erode the cable monopoly. Freston, then leading MTV%20Networks, recognized the paradigm shift toward social media. He orchestrated a meeting in Times Square with a 21-year-old Mark%20Zuckerberg, who arrived in a hoodie and flip-flops in the middle of February. Freston recognized the potential and put a $1.7 billion bid on the table—roughly $900 million in cash and the rest in an earn-out—to acquire Facebook. Zuckerberg turned him down, choosing to remain a "true believer" in his own vision, a decision that eventually made him one of the wealthiest individuals on the planet. This missed opportunity became a weapon for Freston's rival moguls. When Rupert%20Murdoch acquired MySpace for $560 million over a single weekend with zero due diligence, the pressure on Sumner%20Redstone, the volatile chairman of Viacom, reached a breaking point. Redstone, obsessed with Murdoch’s perceived "savant" move into digital, fired Freston, claiming he had let the prize slip away. History, of course, proved Freston right; MySpace eventually dissolved and was sold for pennies years later, while the cable model Freston perfected began its long, slow decline in the face of the creator economy. Leading through disruption in a post-monoculture world Freston’s departure marked the end of an era, but his influence remained. He was immediately contacted by figures ranging from Rupert%20Murdoch to Steve%20Jobs. Eventually, he found himself in a remote jungle in Burma, receiving a message that Oprah%20Winfrey wanted him to consult on her new network, OWN. Freston’s reflection on this career arc highlights a fundamental shift: we have moved from a "monoculture" controlled by editors and gatekeepers to an infinite landscape where everyone is their own broadcaster. His advice for the new generation of entrepreneurs is to find the same alignment he did back in 1980—identify an ascendant industry, match it with personal passion, and build an enterprise that powers creative people. Whether through Substack, Patreon, or the next social platform, the core principles of disruption remain the same: take calculated risks, embrace the aberrant, and never be afraid to chicken-fight at the office holiday party. Success isn't about following a playbook; it’s about having the guts to build the place where the most interesting people want to work.