Overview of How Long Gone — Episode 870: Tom Freston
Chris Black and Jason Stewart host a wide-ranging conversation with Tom Freston (former MTV Networks CEO, media executive and author), mixing casual opening banter (LA weather, GQ event, table reads, masks at shows, restaurants) with a long-form interview about his life, career, media history and current projects. The episode centers on Freston’s new memoir (out Nov 18), his experiences building MTV, international work (notably Afghanistan), the rise and fall of media business models, and reflections on creativity vs. metrics in today’s entertainment landscape.
Key topics discussed
- Tom Freston’s current work: promoting his book and his ongoing board role with the One Campaign (anti-poverty advocacy focused on Africa).
- Early travel and business origins: long-term travels in the 1970s (Afghanistan, India), running apparel trade in South Asia, building a life abroad.
- Afghanistan media project: building commercial and educational TV after the Taliban’s fall; challenges with advertising revenue and programming.
- Rise of MTV and the cable era (1980s–1990s): creative-first approach, MTV News, Unplugged and Real World as cultural touchstones.
- Digital disruption: YouTube, social media, fragmentation and the decline of cable ad economics.
- Vice, HBO and media fumbles: early promise, scale problems, private-equity constraints and wiped-out options.
- Anecdotes: lunch with Fidel Castro (and ensuing U.S. fines), early hashish culture in Afghanistan, dealings with Rupert Murdoch and international media partners.
- Industry trends & challenges: Nielsen ratings accuracy, streaming fragmentation, the overabundance of data, creative risk vs. corporate/financial discipline.
- Personal life: New York/LA preferences, habits (home office), cannabis use, favorite NYC restaurants, and dislikes about hospitality modernization.
Notable insights & quotes
- On work and routine: “Work will expand to fit the amount of time you have.” Freston frames himself as a worker bee who always finds things to do.
- On technology and cultural change: “YouTube was really the game changer.” He credits user-uploaded video and social sharing as transformational for media distribution and discovery.
- On leadership philosophy at MTV: “We weren’t looking so much for the financial results. We were looking for creative results.” He explains staffing networks with creative people to signal priorities.
- On media consolidation and creativity: consolidation reduced the number of bold, tastemaking executives and tightened the margin for risk-taking.
- On modern recommendation algorithms: warns that AI-driven silos could prevent serendipitous discovery — we need randomness (shuffle) to bump into unfamiliar things.
Background & memorable anecdotes
- 1970s travels: Freston hitchhiked the Silk Road, spent time in Afghanistan and India, and developed an entrepreneurial trading life (design and sell garments across regions).
- Afghanistan: early TV work intended to build tolerance and education; later pivoted to NGO-funded educational programs for women (e.g., Malala/Gates-funded content) after ad markets collapsed.
- Hashish culture: recalls Afghanistan’s hashish being widely available and culturally embedded in the 1970s.
- Lunch with Fidel Castro: invited to Cuba for cultural work and music exploration; later fined by the U.S. Treasury for travel violations (about $55,000 fines reported — journalists had exemptions).
- MTV beginnings: launched where cable initially existed (many rural/Midwest cable systems), which explains MTV’s early foothold away from NYC/LA.
Media industry analysis (short)
- Golden era: 1980s–1990s cable expansion created a monoculture, lots of ad money, and room for creative experimentation and big personalities.
- Disruption path: 2000s onward — YouTube (2005), Facebook — shifted attention to the internet; streaming fragmentation followed, making measurement and monetization harder.
- Measurement problem: Nielsen and legacy metrics struggled to adapt to device and platform fragmentation; modern services provide more data, but Freston suggests it can be “too much data” without a single health metric.
- Business model idea: Freston suggests packaging/aggregation (a la old cable bundles) would help consumers, but warns against algorithmic siloing that limits discovery.
- Creative vs. efficiency: consolidation and private-equity pressures compress tolerance for failure; independent companies (A24, etc.) still show creative-first models can work.
Practical takeaways / recommendations
- If you want to understand the pre-digital media mindset, read Freston’s memoir (released Nov 18) — he positions it as an “adventure story with a business story wrapped inside.”
- For music-culture nostalgia or research: MTV Unplugged and the MTV News/Real World archive remain culturally significant; many Unplugged episodes are available on Paramount+.
- For creators/publishers: guard serendipity. Relying purely on algorithmic curation risks losing discovery for both audiences and creators.
- For media consumers: bundles or federated search/aggregators could make streaming simpler and more approachable (and reduce churn).
Who should listen / read this episode
- Media professionals and students studying media history, distribution and business strategy.
- Music industry people and cultural historians interested in MTV’s role in late 20th-century pop culture.
- Entrepreneurs and product people curious about platform shifts (cable → internet → streaming).
- General listeners who enjoy insider stories about television, music, travel and prominent media figures.
Quick TL;DR
- Tom Freston recounts globe-trotting origins, building MTV into a cultural force, the shift from cable-era abundance to streaming fragmentation, and his continuing work in philanthropy and international media (notably Afghanistan).
- He defends a creative-first ethos, warns about over-optimization and algorithmic silos, and shares vivid anecdotes (hashish culture, dinner with Fidel, vice/venture disappointments).
- His memoir is out Nov 18 — pitched as part business memoir, part adventure.
Sponsors mentioned on the episode (brief)
- Squarespace (website builder)
- Skims (men’s line)
- DripDrop (hydration)
- BetterHelp (online therapy)
Action items (from the episode)
- Book: pick up Tom Freston’s memoir (released Nov 18).
- Watch: selected MTV Unplugged episodes and Storytellers / behind-the-music archives (Paramount+ and other services).
- For creators/podcasters: consider measuring core success with a single simple metric (Freston’s comments on “one number” insight).