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SmartLess

"Tom Freston"

with Tom Freston

Published November 10, 2025
View Show Notes

About This Episode

The hosts talk with media executive Tom Freston about his unconventional path from advertising into years of travel across North Africa and Asia, building a clothing business in India and Afghanistan, and eventually helping launch MTV and other major cable brands. Freston recounts the creation and impact of MTV, the birth of Comedy Central, his tumultuous years leading Viacom under Sumner Redstone, early views on platforms like YouTube and MySpace, and his later work in philanthropy and Afghan media. The conversation also explores his philosophy on travel, risk-taking, and using media for social change, plus colorful anecdotes involving Jimmy Buffett, Bangkok sex clubs, and a desert music festival near Timbuktu.

Topics Covered

Television history Music industry and record labels Entrepreneurship Extended travel Travel and tourism Streaming media industry Leadership and management Nonprofit organizations Philanthropic funding War and empire

Disclaimer: We provide independent summaries of podcasts and are not affiliated with or endorsed in any way by any podcast or creator. All podcast names and content are the property of their respective owners. The views and opinions expressed within the podcasts belong solely to the original hosts and guests and do not reflect the views or positions of Summapod.

Quick Takeaways

  • Tom Freston left a conventional advertising career in his mid-20s to travel for years, eventually building a clothing business in India and Afghanistan before returning to the U.S. media world.
  • He was part of the small founding team that launched MTV, helping pioneer the music video format and later expanding Viacom's cable portfolio with Nickelodeon, VH1, and Comedy Central.
  • Freston describes how a defensive move against HBO led to the creation of Comedy Central and how figures like Jon Stewart transformed it into a powerhouse of political satire.
  • His tenure as Viacom CEO under Sumner Redstone ended in a holiday-weekend firing partly tied to not buying MySpace, even though the deal later proved disastrous for News Corp.
  • In later life, Freston shifted focus to global philanthropy, especially through Bono's One Campaign, the RED initiative, and building an Afghan TV network that continues to educate women under Taliban rule.
  • He argues that extended travel when young is a powerful education, critiques today's rush into careers, and remains cautiously curious about AI and the future of media.

Podcast Notes

Host banter and setup before introducing the guest

Headphones, aging, and small physical quirks

Hosts joke about new headphones and seeking compliments[2:33]
• Sean has new headphones and teases the others into complimenting him on how they look
• Will jokingly accuses him of setting up the whole conversation just to get praise for the headphones
Running gag about making a noise when getting in and out of cars[3:25]
• They reference Jason Bateman having normalized the habit of grunting or making a noise when getting out of a car
• Jason notes he has been doing this since his mid-30s and realizes it's an "old man" behavior

Technical competence among the three hosts

Discussion about who has the most tech problems[4:11]
• Sean admits Scotty bails him out of tech issues, which may enable him
• They agree Will has the least technical problems because of his podcasting experience and familiarity with audio gear
Joke about Will being an original Geek Squad guy[4:48]
• Will jokes that he still owns the name and did all the art, clearly in jest

Sports outing story and social awkwardness

Jason and Sean at Dodgers and USC football games[4:59]
• Sean recounts going with Jason to a Dodgers game and a USC football game, noting how much junk food Jason bought
• Sean describes himself holding multiple concessions, looking like he is at a state fair with armfuls of food and drinks
Awkward encounter with people sitting in their seats[5:45]
• They arrive late, find people in their seats, and feel the whole stadium judging them as entitled actors kicking out a family
• Because tickets are now on phones, they have to pass a phone down the row rather than paper tickets, which Jason dislikes
• The family in their seats refuses to move, claims an usher placed them there, and insists the hosts find the usher to relocate them
• Jason and Sean end up sitting on the stairs with the food until ushers move the family; then they sit with extra empty seats and feel like "super assholes"
• Sean spills his cheese dipping sauce on the stairs, which becomes a subject of crude jokes

Introduction of guest Tom Freston and overview of his career

Will's elaborate introduction of Tom Freston

Sketching Tom as an adventurous, worldly figure[7:13]
• Will calls Tom "the pride of Connecticut, sort of" and describes him as the kind of guy you'd find on a night boat to Tangier
• He notes that Tom ran a clothing company out of Afghanistan and India in the early 1970s, when almost no one was going there
• Will says Tom ran clothing illegally across the St. Lawrence River into upstate New York to avoid tariffs
Listing Tom's media and philanthropic accomplishments[7:58]
• Will credits Tom with creating MTV and changing how people saw music, fashion, and culture on a global scale
• He mentions Tom running networks like Nickelodeon, VH1, and Comedy Central and becoming CEO of Viacom
• Will notes that Tom is now chair of the One Campaign, fighting poverty, and calls him the coolest guy and a friend

Tom joins and initial rapport with hosts

Tom jokes about calling the show "Shameless"[8:33]
• He says he often refers to Smartless as "shameless", clearly as a tongue-in-cheek compliment
How Will and Tom met through Jimmy Buffett[8:52]
• Tom says they met just hanging around New York and Long Island
• Will explains they were introduced years ago by Jimmy and Jane Buffett
• They briefly acknowledge Jimmy Buffett's passing and his talent for introducing people and bringing friends together

Tom's early years: meeting Jimmy Buffett and pre-MTV life

Tom meets Jimmy Buffett in 1970s Manhattan

Description of JP's bar and music-industry nightlife[9:33]
• Tom met Jimmy Buffett in the basement of a bar called JP's in Manhattan in 1977, a music-industry hangout that would spill into daylight at 5 or 8 a.m.
• He recalls traveling with Jimmy frequently, especially after Jimmy bought a jet, and notes Buffett was serious about flying seaplanes and larger aircraft
Buffett's plane crashes and training flights[10:02]
• Tom confirms Jimmy crashed a seaplane in Nantucket, flipping it over, and had other incidents he calls "malfeasance"
• Will tells a story about Jimmy inviting him on takeoff-and-landing practice flights, and Jimmy's wife Jane warning Will that Jimmy had crashed planes and he should not go

Leaving advertising for travel and starting a clothing business in India and Afghanistan

From ad agency work to crossing the Sahara

Tom's dissatisfaction with mainstream advertising jobs[11:25]
• Tom worked at an ad agency in New York on accounts like Charmin toilet paper, dealing with Mr. Whipple, which he calls a tough account
• Before Charmin he was on the G.I. Joe account, which he characterizes as the war toy of the military-industrial complex
Impulsive decision to travel and cross the Sahara[11:41]
• His former girlfriend called from Paris urging him to quit and join her to cross the Sahara Desert
• He quit his job and within a week was on a plane; they traveled together, then she left and he kept traveling for about a year

Discovering India and Afghanistan and deciding to stay

Being lured to India as "the greatest show on Earth"[11:58]
• A woman he met told him he had to go to India because it was the greatest show on Earth, which led him to travel there
• He fell in love with both India and Afghanistan, describing them as feeling like another planet at that time
Staying from 1972 to 1979 and building businesses[12:15]
• Tom dates his long stay as 1972 through 1979
• He started a couple of businesses, designing and making higher-quality clothes to sell to U.S. retailers like Bloomingdale's
• He describes having a house in Delhi, being able to travel widely, and "living like a pasha"

Tariff shock, embargo, and smuggling clothing into the U.S.

Jimmy Carter embargo ends his import business[12:41]
• Tom says Jimmy Carter imposed an embargo banning clothing imports from India, similar to modern tariff disputes
• He already had significant production underway and calls it a nightmare to work there at that time, so the embargo left him exposed with lots of inventory
Smuggling three tons of goods via Canada[13:00]
• Because imports to Canada were still allowed, he decided to smuggle about three tons of clothing from Canada into the U.S.
• He notes that during his years abroad, he met many smugglers who explained how easy it was to move contraband into the U.S., influencing his decision
• He tapped a Canadian acquaintance whose father had been a rum-runner; that man was eager for another cross-border run
• They drove through the Thousand Islands area where borders are indistinct and many boats are on the water, and he remarks that immigration enforcement like ICE did not exist then
• Tom states it felt foolish in retrospect, but at the time he did not feel like he was truly committing a crime and was trying to recoup losses from what felt like government betrayal with no prior notice
Afghan business collapse due to communist coup[14:08]
• He notes that his Afghan business also "vaporized" after a communist coup in Afghanistan, ending that enterprise as well

Motivations for dropping out, travel culture of the 60s and 70s, and effects on his worldview

Why Tom rejected a mainstream life despite an MBA

Alienation and desire for freedom in the 1960s[15:18]
• Tom describes the 1960s as a time of widespread alienation when freedom looked very attractive compared to corporate life
• He says he decided early he did not want a mainstream life and had spent about 18 years in school, which left him feeling ready to break out
Using graduate school to avoid the draft[15:32]
• Tom confirms he earned an MBA and explicitly says this was a way to stay out of the draft at the time
Advertising work was unfulfilling[15:09]
• He bluntly says his mainstream advertising job "wasn't fun" and references selling toilet paper as emblematic of that dissatisfaction
• He notes many people were quitting jobs to go do their own thing, and he saw leaving as a way to stretch himself beyond an 18-year school-to-office pipeline

Hippie trail, long-term travel, and impact on youth

The European "hippie trail" phenomenon[17:21]
• Tom explains that in Europe, dropouts often headed south along the so-called hippie trail to Morocco, India, and Lebanon, rather than communes in cold northern regions like U.S. dropouts
• He says many people tried to see how long they could travel, and he met people who had been on the road for years
Arguing that more travel and "dropping out" would benefit today's youth[18:10]
• Tom believes the world could use more of that long-term travel mindset today, as many kids are anxious and experience panic attacks around school and career pressure
• He describes meeting recent graduates who say they are starting their career the Monday after graduation, and contrasts that with taking time off to let the world educate you

Influence of travel on his children

Encouraging sons to travel and be self-sufficient[18:37]
• Tom says he has encouraged his sons to travel and is proud that they are comfortable going anywhere and making their own plans
• He notes they have not done multi-year trips as he did, but do take substantial trips despite being caught up in modern pressures

Language skills and transition back into U.S. media via MTV

Language learning in India and Afghanistan

Using English and local languages[19:51]
• Tom notes that in India, English is widely spoken due to British colonization, which made it easier to get by, though he could operate somewhat in Hindi
• In Afghanistan he learned enough Dari (a dialect of Farsi) to manage in bazaars, order food, and take taxis, though he says he retains little now

Choosing music and MTV after losing his businesses

Deciding what he loved after being "wiped out"[21:05]
• When his life overseas collapsed, he asked himself what else he truly loved and identified rock music as his major passion
Finding opportunity in cable and music videos[21:14]
• He read in Billboard about a plan to start a video music channel as part of the emerging cable "TV revolution"; the parent company already had Nickelodeon and The Movie Channel
• Through a connection of his brother, he got an interview at Warner Amex Satellite Entertainment, a joint venture of Warner and American Express
Hired onto the initial MTV launch team[21:25]
• Tom interviewed with Bob Pittman, a 26-year-old radio programming star nicknamed "the long-haired, one-eyed hippie", who had worked with Don Imus
• The company said they wanted people with no television experience, which Tom used to his advantage, saying there was no TV where he had been for eight years and emphasizing his music fanaticism and business background
• Pittman teased him about being a hashish smuggler, inferred guilt from Tom's "not really" answer, and then hired him onto the founding MTV team
• The initial MTV team was small, including Bob Pittman, Tom, John Sykes, Steve Casey, Carolyn Baker, Sue Steinberg, and Fred Seibert as key creative, tasked with getting MTV on air by August 1 within about eight months

Creating MTV, the rise of music videos, and cultural impact

Early state of music videos and inspiration from Europe

Music videos existed mainly in Europe before MTV[26:54]
• Tom explains that in Europe, regulated radio stations played little music, so record companies made videos shown in record stores and on shows like Top of the Pops
• In the U.S., there was minimal awareness of music videos when MTV started
• He recalls spending a summer in Berlin watching videos all day in his girlfriend's record store, thinking it was a "video wonderland" and that people would love the format

First videos and branding MTV with NASA footage

Video Killed the Radio Star and early iconic videos[27:56]
• Tom confirms that "Video Killed the Radio Star" was the first video MTV aired
• He agrees Dire Straits had early videos, and later notes their song "Money for Nothing" became pivotal for MTV's identity
Using NASA footage and a cheap logo to launch the brand[28:18]
• With little money, MTV used public-domain NASA footage of rocket launches and moon landings, effectively "ripping off" humanity's greatest moment to brand their channel
• They bought the now-iconic MTV logo from designers in Tribeca for about $1,000

Dire Straits, "Money for Nothing," and the "I want my MTV" campaign

"Money for Nothing" as critique and gift[28:42]
• Tom says "Money for Nothing" portrayed MTV as vapid and critiqued the corporatization of music videos, yet the repeated line "I want my MTV" became a massive gift
• They had Sting sing the "I want my MTV" line, and that song's global reach meant people around the world knew MTV partly through it
Grassroots pressure on cable companies through viewer demand[28:10]
• Cable operators, typically older men, disliked MTV, did not understand it, and saw it as a margin threat, so they resisted carrying the channel
• For the first years MTV was largely in Midwest towns like Tulsa, where viewers loved it, but not in New York or Los Angeles where media lived
• MTV devised the "I want my MTV" campaign to get fans to call their cable companies and demand carriage, which Tom says worked very well

Cultural peak: Thriller and Live Aid

Michael Jackson's Thriller and big-budget videos[28:40]
• Tom marks the release of Michael Jackson's "Thriller" and "Beat It" videos as a breakthrough when major artists started creating high-production videos that were irresistible
Live Aid cementing MTV's legitimacy[28:55]
• Bob Geldof approached ABC about Live Aid and they agreed to air only three hours of highlights, whereas MTV offered to run the full 16 hours because they "had nothing else to do"
• The Live Aid broadcast became MTV's biggest show ever and powerfully legitimized the channel

Role of music videos and directors, and MTV's evolution'

Impact of videos and their continuing life online[30:01]
• Tom notes that music videos are still made in large numbers, often more economically, but are now mainly consumed via on-demand platforms like YouTube and Vevo rather than MTV
Directors get credit and careers via MTV[31:26]
• After a few years, directors demanded on-screen credit; MTV added their names at the end, helping launch careers of filmmakers like David Fincher, Spike Jonze, Russell Mulcahy, and others
MTV as a revolutionary visual language that later became outdated[30:56]
• Tom says people forget that, for its day, MTV was revolutionary and created a new visual language, even though media has since advanced far beyond that point
MTV's decline as a music-video channel[30:30]
• He clarifies that recent shutdown announcements were about UK channels that still played videos; the main MTV channel in the U.S. runs reality shows, which he says bothers him but continues to exist
• He argues the linear video-channel business model had to die once all videos were freely available online with no exclusivity, making growth impossible
• Tom believes the new Paramount ownership might reimagine MTV digitally to be more interesting than today's siloed, algorithm-driven media offerings

Creating Comedy Central and expanding Viacom's cable networks

Responding to HBO's planned comedy channel

Immediate counter-announcement strategy[32:26]
• Tom recalls being in a staff meeting when someone slipped him a note that HBO had announced a new comedy channel called The Comedy Channel
• He responded by deciding they would announce their own comedy channel the same day so every story about HBO's plan would also reference them as a competitor
• At that moment they had no name or concept, only the idea that they could build something similar to their late-night "Nick at Night" repackaging of old shows
Guerrilla competition with HBO and eventual merger[32:54]
• They engaged in a multi-year battle with HBO's channel, with Viacom executive Frank Biondi fully backing an aggressive counter-attack due to his own fraught history with HBO's Michael Fuchs
• Tom characterizes their strategy as a "guerrilla operation" fighting against a richer rival, and says HBO was surprised they did as well as they did with what was largely smoke and mirrors
• The two channels eventually merged, forming Comedy Central as a joint entity

Naming and early programming of Ha! and Comedy Central

Launching Ha! The TV Comedy Channel[33:50]
• A couple of days after their counter-announcement, they named their channel Ha! The TV Comedy Channel, with an exclamation point and a logo Tom liked
• He notes HBO's Comedy Channel plan largely involved repurposing funny scenes from TV and movies with stand-up segments and VJ-style hosts, which they had tried before and doubted would work
• Their counter-approach was to air full comedy shows, and they sought headlines by hiring Fred Silverman, doing deals with Brian Grazer, and licensing material from Norman Lear
• They acquired the original five years of Saturday Night Live (1975-1980), using such acquisitions to build a credible lineup
Choosing the name Comedy Central after merger[33:34]
• After the merger of Viacom's Ha! and HBO's The Comedy Channel, the combined team from both companies settled on the name Comedy Central

Jon Stewart, The Daily Show, and political satire roster

Jon Stewart's path to The Daily Show[33:40]
• Tom explains that Jon Stewart had earlier hosted The Jon Stewart Show on MTV in the late 80s and early 90s, so he was already in their talent stable
• The first host of The Daily Show was Craig Kilborn; later they replaced him with Jon Stewart
Reframing The Daily Show as news satire[33:40]
• Stewart proposed that instead of just doing pop culture, they should satirize the news and he would play a fake newsman
• Tom remarks that Stewart found his voice this way and kept improving, and he still watches him on Monday nights and calls him brilliant, even saying he should run for president
Comedy Central as launchpad for major comedic voices[34:20]
• Tom lists Jon Stewart, Stephen Colbert, John Oliver, Samantha Bee, Bill Maher, and Dave Chappelle as talents that emerged from Comedy Central programming
• He notes Politically Incorrect with Bill Maher began on their channel before ABC picked it up, later fired Maher, and he moved to HBO
• He also cites Jimmy Kimmel's The Man Show and Steve Carell as Comedy Central alumni, and calls the channel a good launching place for young talent
• Tom observes that many frontline "resistance" voices in U.S. politics are now comedians like Colbert, Kimmel, and Maher, many of whom trace roots to Comedy Central

Leading Viacom, MySpace, YouTube, Vice, and reflections on media industry changes

Serving under Sumner Redstone and getting fired

Pattern of CEOs being fired on holiday weekends[35:36]
• Tom explains that Sumner Redstone fired every CEO, including him, often on holiday weekends like the 4th of July, Memorial Day, and Labor Day
• He quips that being hired as CEO by Sumner essentially meant your days were numbered, and if you survived the summer holiday season you probably had another year

MySpace non-deal and being blamed for it

News Corp buys MySpace and Sumner's anger[35:56]
• Tom says Sumner had never heard of MySpace until he saw Rupert Murdoch buy it and be celebrated as a new media visionary on trade magazine covers
• Viacom had kicked the tires on MySpace but never bid; Sumner became annoyed that Rupert got the visionary credit and that Viacom had not bought it
• He notes Murdoch paid about $560 million for MySpace and later sold it for around $30 million, joking he is still waiting for a thank-you note because this decision was cited in his firing

Early appreciation of YouTube and missed acquisition

What YouTube was at inception[36:36]
• Tom describes YouTube circa 2005 as a free destination for user-generated video where anyone could upload anything, others could comment, and people could send clips to one another
• He characterizes it as a new kind of social media, with person-to-person communication outside traditional gatekeepers
• Media companies started using YouTube as a promotional vehicle, such as Saturday Night Live posting Andy Samberg clips
Why Viacom did not buy YouTube[37:06]
• Tom and his team believed they needed to own a digital platform and wanted to bid on YouTube, recognizing its revolutionary nature and threat to MTV's role
• Google ultimately bought YouTube for about $1.6 billion, which Tom now calls the deal of the century given YouTube's approximate $600 billion valuation
• Viacom's board considered YouTube a copyright-infringement machine that would expose them to lawsuits; after Tom left, Viacom sued YouTube for $1 billion and lost roughly a decade later

Work with Vice Media and its rise and fall

Vice's HBO era and partial collapse[37:50]
• Tom says he worked with Vice for several years, calling it a wild and fun ride that could be its own book
• Vice had a strong run with its HBO series and a suite of YouTube channels, but later imploded and now survives as a smaller studio operation

Losing interest in day-to-day media work

Perception that fun and money have been drained from media[38:02]
• Tom says he is content not to be in media today, feeling that much of the fun and money have been taken out, and many companies are stripped down and forced to consolidate
• He contrasts this with his earlier career, when the business felt more optimistic and ascendant

AI, the future of media, and hypothetical career choices today

Reflections on AI's potential and risks

Conflicting narratives about AI[38:35]
• Tom summarizes current AI discourse as ranging from doomsday predictions of machines killing us to utopian visions of a great new world with 20% unemployment, reflecting uncertainty
• He notes enormous investment sums and says he is curious and watching developments, while acknowledging many brilliant technologists are steering things from "up north" (Silicon Valley)

Would 26-year-old Tom enter media again today?

Choosing sectors that are ascendant[39:52]
• Asked what he would do today as a 26-year-old, Tom says he would aim to work in something he really liked, probably gravitating to entertainment or media again
• He emphasizes aligning with an ascendant business so that joining at the right place and time creates upward mobility
• He expresses confidence that the industry will find ways to integrate AI without putting everyone in entertainment out of work
Example of AI newscasters in the UK[40:35]
• Tom mentions Channel 4 in the UK using AI-generated newscasters that look exactly like real people, illustrating AI's encroachment into media roles

Philanthropy, One Campaign, RED, and Afghan media work

Working with Bono and the One Campaign

Shift into nonprofit work focusing on poverty and disease[41:14]
• Tom says he is in a life chapter centered on not-for-profit work, and has worked with Bono for about 18 years
• He served as board chair of the One Campaign, which focuses on extreme poverty and infectious disease in Africa
• He mentions RED, associated with consumer products like Apple devices, as another initiative tied to funding global health, allowing him to stay connected to the private sector
• Tom says this work lets him explore Africa more and that he finds it satisfying, not merely "giving back" but something he enjoys

Founding and evolving a TV network in Afghanistan

Returning to Afghanistan to build a TV station[42:26]
• Tom never lost his fascination with Afghanistan and returned for about 10 years to build a TV network there, until the Taliban returned to power
• He saw TV as a tool to change society, connect Afghans to each other and to the outside world, and especially to help liberate women
• He notes that simply having male and female newscasters side-by-side sends a profound social signal, and they reintroduced music and the arts that had been banned by the Taliban
Impact of Taliban return, funding shift, and educational programming[43:01]
• Before the recent Taliban takeover, the network had around 250 advertisers, which has shrunk to about one (an energy drink brand) due to conditions and bans on alcohol
• They pivoted from commercial broadcasting to producing educational programming for women, focusing on non-ideological subjects like mathematics and physics
• Funding now comes from foundations such as the Gates Foundation and the Malala Fund, and content is produced in Afghanistan with curriculum help from Afghan educators in the diaspora
• Tom says women have been effectively erased from public spaces in Afghanistan and are often not allowed to speak publicly, leaving many highly educated women stuck at home and extremely depressed
• The educational programming keeps about 500 people employed and provides some avenue of learning for women and girls despite severe restrictions

Colorful anecdotes: Bangkok sex club with Sumner Redstone and Timbuktu music festival with Jimmy Buffett

Taking Sumner Redstone to sex clubs in Bangkok

Sumner requests a trip to Bangkok and sex clubs[44:19]
• Tom repeatedly urged Sumner to visit Asia to see MTV's growth in countries like India, China, Taiwan, and Indonesia
• Sumner eventually agreed but specified he wanted to go to Bangkok, a market where Viacom had minimal business at the time
• In private, Sumner told Tom he wanted to visit sex clubs, so Tom had to do advance scouting of Bangkok's red-light districts despite not being experienced in that scene
Witnessing extreme performances and local indifference[44:56]
• Tom describes one club full of regular Thai patrons where a couple, naked and greased up, descended slowly on a small Harley-like motorcycle from the ceiling while having sex as the man revved the engine
• He notes that locals quickly stopped paying attention and went back to their drinks while people had sex two feet above, illustrating how normalized it was
• Tom says he shepherded Sumner through multiple clubs as a loyal employee, and jokingly contrasts this with simply watching MTV instead of flying halfway around the world

Desert music festival near Timbuktu with Jimmy Buffett

Traveling by private jet to Timbuktu for a festival[45:24]
• Tom recounts flying with Jimmy Buffett, Chris Blackwell, Bill Flanagan, and others to Bamako, Mali, then taking Jimmy's jet to Timbuktu for a desert music festival featuring Tuareg people
• At the remote Timbuktu airport, their plane was the only one and locals rushed the aircraft trying to sell daggers, underscoring their isolation
Near-misdirection to an Al-Qaeda camp and rescue by a hitchhiker[45:45]
• They drove for hours through sandy terrain with a local guide, until their security man realized they were headed the wrong way and toward an Al-Qaeda camp known for kidnapping tourists
• The security guard pulled the local into a headlock, put a gun to his head, and threatened to kill him, leaving Tom horrified at the prospect of witnessing a murder in the desert while wearing a turban
• At Jimmy's urging they spared the guide and left him in the desert, then picked up a hitchhiker whose Bob Marley ringtone and claimed knowledge of the route convinced them to let him navigate to the festival

Hosts' closing reflections on Tom's life and the value of travel

Admiration and envy of Tom's adventurous life

Feeling uplifted and depressed by comparison[46:35]
• After Tom signs off, Jason says he feels both uplifted and depressed listening to Tom's life, envying the scope of his experiences
• He recalls a time in his mid-20s, during a dry spell in his career, when he considered going to the international terminal at LAX, picking a destination at random, and starting over

Discussion about timing of travel and its impact

Wondering if travel later in life changes you as much[46:48]
• Jason questions whether traveling extensively at age 60 would be as meaningful or mind-changing as doing it at 25, or whether by then one is too set in their ways
• Will and Sean suggest the only way to know is to do it, and Will says Tom's story makes him want to tell young people to put their phones down and get out into the world
Recognizing how Tom brought travel-derived perspective back into media[47:26]
• Will observes that Tom not only traveled but then brought that broadened worldview into corporate media, which set him apart and fueled ideas like MTV, Comedy Central, and interest in YouTube
• They highlight Tom's ongoing curiosity as a key trait, noting he still travels to places like Albania, meets prime ministers, and stays engaged with global issues

Closing gratitude and humor

Praising Tom's book and life as inspiration[47:34]
• Will references Tom's book title as "An unplugged adventures from MTV to Timbuktu" and reiterates how much he enjoyed it, describing devouring it and urging listeners to read it
Final joke about staying curious and having fun[48:12]
• They conclude that Tom's story underlines the importance of staying curious and interested, and Will signs off with a light, self-referential joke about having had a good time together

Lessons Learned

Actionable insights and wisdom you can apply to your business, career, and personal life.

1

Stepping outside the mainstream early in life, especially through extended travel, can radically expand your perspective and provide raw material for later creative and professional breakthroughs.

Reflection Questions:

  • • What obligations or fears are currently keeping you from taking a significant break or journey that might broaden your worldview?
  • • How might spending even a few weeks immersed in a completely different culture change the way you see your current career or life path?
  • • What concrete step could you take in the next 6-12 months to create space for a meaningful period of exploration or travel?
2

In fast-moving industries, seizing the narrative quickly-even before every detail is figured out-can neutralize larger competitors and create strategic breathing room.

Reflection Questions:

  • • Where in your work or business are you waiting for perfect information instead of staking out a position early like Tom did with the comedy channel announcement?
  • • How could a bold public commitment or preemptive move shift the balance of power with your current competitors or stakeholders?
  • • What is one initiative you could announce or pilot in the next quarter that would force you and your team to commit and then figure out the details?
3

Staying attuned to new platforms and user behaviors, and being willing to pivot away from legacy models, is essential to avoiding obsolescence in any field.

Reflection Questions:

  • • Which emerging tools, platforms, or behaviors in your industry are you currently underestimating or dismissing the way many dismissed early YouTube?
  • • How could you carve out regular time to experiment with new technologies without immediately needing them to generate revenue?
  • • What is one small, low-risk experiment you could run this month to test a new channel, format, or audience you are curious about?
4

Media and storytelling can be powerful levers for social impact when intentionally directed toward issues like poverty, health, and education.

Reflection Questions:

  • • What social or global issue genuinely moves you that could benefit from better storytelling or visibility?
  • • How might you repurpose your existing skills (communication, design, management, etc.) to support a cause in a way similar to Tom's work with One, RED, or Afghan TV?
  • • What is one concrete collaboration, volunteer role, or project you could pursue in the next year to align your work more directly with a social impact objective?
5

You can reinvent your career in distinct chapters, moving from building companies to leading corporations to focusing on philanthropy, as long as you keep your curiosity and willingness to start new things.

Reflection Questions:

  • • If you divided your life into chapters like Tom does, what would the current chapter be titled and what would you want the next one to be about?
  • • How could you begin transitioning some of your time and energy toward the kind of work you imagine for your next chapter without abruptly abandoning the current one?
  • • What skill, relationship, or habit should you start cultivating now to make a future reinvention smoother and more intentional?
6

Gatekeepers eventually lose their exclusive power as technology enables more direct, decentralized participation, so clinging to control is less effective than learning to collaborate with new ecosystems.

Reflection Questions:

  • • In what areas of your work are you still thinking like a gatekeeper instead of designing for open participation and user contribution?
  • • How might your strategy change if you assumed that your audience, customers, or users will increasingly expect to create, remix, or directly interact with your product or content?
  • • What partnership, platform, or community could you engage with this year to better position yourself within an evolving, more decentralized landscape instead of against it?

Episode Summary - Notes by Sawyer

"Tom Freston"
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