Episode 324 · Post-Ben
Two Greatest Minds of The Century (Gary Vaynerchuk) | The Tim Dillon Show #324
with Gary Vaynerchuk
Nov 20, 2022 · 1:07:43 · 463,000 views · 24 segments, 149 moments indexed
Tim Dillon sits down with Gary Vaynerchuk aka (Gary Vee) to talk about topics such as FTX, a possible rebrand for Poland, how the Weinstein Company could make a comeback, Vee Friends, and some talk about The Crypto Winter.
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- 1 min
Tim opens by thanking Gary for having a sense of humor about being mocked, and Gary explains growing up in Jersey being roasted constantly and how he genuinely loves comedy and views mockery as flattering.
5moments
- Gary Vaynerchuk thanks Tim for having a sense of humor about the water bottle joke.
- Tim asks why Gary doesn't get mad when people make fun of him, while most people get viciously angry.
- Tim explains comedians make fun of themselves and everyone else as part of the job, including roasting Joe Rogan with a terrible high-pitched imitation.
- Gary says he doesn't get upset because he's flattered to be known enough that comedians joke about him.
- Growing up in Jersey in the 80s and 90s meant being surrounded by friends making fun of each other constantly.
- 3 min
They discuss whether Elon Musk's purchase of Twitter was a mistake, with Gary arguing Twitter could become a subscription-based Netflix/Amazon Prime competitor and that Musk's operational track record makes him likely to succeed.
4moments
- Tim transitions to Elon Musk buying Twitter, calling it a big mistake or maybe not.
- Twitter hasn't really evolved much from 2007 to today, which Elon will likely try to fix.
- Tim believes Twitter could be a major challenger to Netflix and Amazon Prime as a streaming platform.
- The platform works as an over-the-top streaming service if Elon figures out the subscription model.
- 2 min
Tim jokingly presses Gary to remain a 'believer' in Sam Bankman-Fried and FTX despite the collapse, riffing on getting him to Dubai and comparing him to Bill Clinton-style donations.
5moments
- Guys who actually built real companies are less likely to fail than those who are all sizzle and no substance.
- In comedy, Tim knows people with more raw talent who never made it because they wouldn't put in the work.
- Everyone gets exposed in the end if they can't actually operate and do the work.
- People are jumping ship on FTX when they should be showing support, especially since Bankman-Fried is giving money to Bill Clinton and Democrats.
- Tim asks how to help Bankman-Fried, wondering if they should get him to Dubai or on a podcast.
- 3 min
Gary argues the FTX collapse doesn't kill crypto, distinguishing decentralized believers from people like Gisele Bundchen who parked money in unregulated exchanges, comparing it to the dot-com bust and pets.com era.
8moments
- People educated in crypto didn't keep money in exchanges because that's not decentralized.
- These crypto setbacks mirror the pets.com era around 2001 when people got hyped about dumb stuff they didn't understand.
- Centralized exchanges are dangerous—unregulated platforms where Sam Bankman-Fried pulled off exactly what people should fear.
- Crypto in general isn't well understood by the public, which creates vulnerability.
- Bitcoin has real enthusiasm because hardcore technologists actually wanted decentralization, not like the NFT hype.
- Sam Bankman-Fried's damage came from people's lack of knowledge, not from his blockchain expertise.
- The crypto boom differs from the dot-com bubble because back then people didn't have personal money in public stocks like pets.com.
- Today's young people think they're investors and throw around money like crazy in a way 1995 internet investors didn't.
- 4 min
Gary explains his long-standing take that NFTs are exciting technology even though 99% of projects will go to zero, and Tim brings up a friend's absurdly profitable snail NFT as a symbol of economic madness.
8moments
- Tim attended Art Basel where everyone was talking about NFTs.
- 99% of NFT projects are going to zero, yet the excitement lives on anyway.
- Internet hysteria in 1996 looked identical—everyone said everything would be online in 24 months, but nobody over 40 even knew how to get online.
- Amazon was four dollars a share in 1999; one percent of the noise will turn out to be special, but people get too greedy too fast.
- A buddy bought an NFT of a snail with a cigar up its ass for 80 bucks and it became worth 44,000—a perfect statement of the economy.
- Tim worked in subprime mortgages and believes speculation can be beautiful; people should be allowed to take financial chances.
- There will be a Jackson Pollock and an Andy Warhol of the NFT generation—three to four artists whose work people will collect vigorously in 25 years.
- That real talent represents point zero one percent of all the artists making NFTs.
NFTsAmazonAndy WarholJackson PollockArt Basel
- 2 min
Gary compares the NFT collectible boom to 1980s cartoon IP creation like Transformers and Care Bears, predicting a few NFT projects will become legendary collectibles decades from now.
4moments
- 80s cartoons like Transformers, GI Joe, and My Little Pony were built by real creative people developing intellectual properties.
- Tim argues those surviving cartoons will become important art and collectibles, unlike NFTs.
- The conversation turns to whether being proactive is hustle culture, with Tim defending proactivity.
- Tim questions whether this piranha NFT character is meant to teach children about NFTs.
GI JoeMy Little PonyTransformersCare BearsGhostbusters
- 2 min
Tim mocks Gary's VeeFriends characters like the Proactive Piranha and Accountable Ant, joking about hustle culture and grooming kids into blockchain talk, while an Athletic Greens ad plays mid-riff.
3moments
- Trans teachers grooming kids into being trans is what VeeFriends is actually about.
- Tim pitches Athletic Greens as a way to groom kids into becoming entrepreneurs and robbing their families.
- Getting kids to talk about NFTs and blockchain at the dinner table and school lunch as a recruitment strategy.
- 1 min
Gary explains VeeFriends is meant to educate kids toward a 'purple' middle-ground worldview rather than red/blue extremes, with plans to develop the character universe like Marvel over decades.
3moments
- Tim's purple philosophy: in a world of red and blue, all the answers are purple, which is why VeeFriends aims to educate people to play in the middle.
- Accountable Ant is a character Tim wants to build—an ant that gets called out for saying something wrong and understands that most people blame somebody else instead of themselves.
- Tim plans to build these characters over the next 50 years, like Marvel, scaling from young cartoons and toys to content for ages 1 to 99.
- 4 min
They discuss the growing chasm between the ultra-wealthy and the disenfranchised, with Gary saying he believes in merit but is troubled by people who avoid taxes and by systemic inequality, invoking his communist-born parents' immigrant story.
8moments
- Tim describes the vast chasm of wealth inequality between people at the top and bottom of society.
- We're probably going to live to see trillionaires while large swaths of the country lack clean water.
- Tim says he struggles with suppressing merit because it doesn't feel right to the human spirit.
- The thought of people making hundreds of millions a year not paying taxes or contributing feels wrong.
- His message is about sharing things he observes that might help people, though it doesn't work for everyone.
- Tim's friends who are entrepreneurs and capitalists want merit to actually matter in the system.
- The FTX and Bernie Madoff cases show how easily the system can be gamed despite talk of merit.
- Humans are flawed—fraud happens, and there are bigger problems like people killing each other for no financial benefit.
wealth inequalityFTXBernie Madoffmarketing gurus
- 1 min
Tim uses a toy rattlesnake as a prop to get Gary's read on the irrationality of the Russia-Ukraine war, including a riff on a missile hitting Poland as a 'rebrand opportunity.'
4moments
- Tim asks if there's an animal that can explain the Ukraine war
- Tim notes Zelinski seems to be doing a good job, but a missile just hit Poland
- Poland has nothing going on and needs a rebrand opportunity after being hit by a stray missile
- Tim suggests Poland should march in and own the missile hit as a branding strategy
- 3 min
Gary praises Tim's comedy as necessary escapism, then reflects on real economic hardship (a mother with cancer and no healthcare) versus hustle culture messaging, before telling stories about his strict immigrant Belarusian upbringing.
6moments
- Tim explains why escapism and comedy matter: people need both genuine escapism and passion for actionable change when things get tense.
- Wealth separation has been Tim's primary topic with friends for 25 years—the root cause of good places deteriorating.
- Real-world example: someone wants to hustle and succeed, but their mother has cancer and no health insurance, unable to afford medication despite years of work.
- Tim's parents each lost a parent young and lived in the USSR; his mother came to America in 1978, giving him firsthand perspective on actual communism.
- His father gets frustrated when Americans call the country socialist, breaking into his accent to tell them they have no idea what communism actually was.
- Growing up Russian, Tim's mother was tough about pain and sickness—if he broke his arm, she'd tell him to go to sleep rather than get medicine.
separation of wealthUSSRChris Rock
- 3 min
They debate a spate of articles claiming people are sick of social media, with Gary saying he'd be thrilled if platforms disappeared since he only cares about following audience attention wherever it goes.
8moments
- Tim agrees social media engagement is down based on recent articles.
- People are sick of social media and realize how toxic it is, potentially unplugging from it entirely.
- The internet may no longer be the sole driver of culture, replaced by Netflix, podcasts, or other platforms.
- Tim would be pumped if social media disappeared since he only cares about following where attention goes.
- Social media's toxicity comes from people themselves being toxic, and the platform allows them to express it.
- People approach Tim at the airport asking about Instagram, which he describes as just people drinking drinks out of hot dogs.
- Social media is a portal to Hell that people have collectively opened.
- Tim jokes that if he ends up in hell, he'll colonize it quickly and dominate it.
- 3 min
Gary argues fame has been commoditized, plugs his employee Sean as a future comedy star, jokes about predicting his rise for selfish reasons, and gives mock advice for Sam Bankman-Fried to get therapy for 'fraudsville.'
7moments
- Tim argues that nobody deserves fame less than anyone else—if a girl eats different sausages on Instagram, she deserves to be famous.
- Fame has been commoditized and now everybody has some sort of audience, which Tim thinks is awesome.
- Gary Vee predicts Sean will be as big as Tim in three years, describing him as a future comedic superstar at his media platform.
- Tim admits his prediction about Sean was purely selfish—he said it so he could claim credit in four years.
- Everything I say publicly, I want to be right about, which is why I'm petrified to be wrong—authenticity matters.
- Sam Bankman-Fried should get therapy to understand how he ended up in fraudsville, according to Tim's advice.
- Better Help online therapy will help Sam Bankman-Fried deal with his fraud situation, Tim suggests.
- 6 min
Gary explains VaynerMedia is Mad Men for the social era serving companies not individuals, they riff on Cold Stone Creamery marketing to 'fat and sad' people, discuss admired entrepreneurs like Evan Williams, Sarah Blakely, and Mr Beast, and the segment drifts into an ExpressVPN sponsor read.
10moments
- People don't understand what VaynerMedia does—Tim compares it to Mad Men, a large advertising firm that helps companies connect with audiences on social media.
- Companies are the clients, not people—Gary and Tim discuss targeting Cold Stone Creamery customers and the markets built on people doing their own thing.
- Fortune 500 companies waste enormous amounts of money on traditional TV commercials and banner ads instead of smarter marketing strategies.
- Gary Vaynerchuk's favorite entrepreneurs: Evan Williams, who co-founded Twitter and understood consumer needs better than most.
- Sarah Blakely and Spanx represent what excites him—people who recognize what the masses actually want before the market exists.
- Someone convinced the world to buy bottled water when it was free—an example of entrepreneurship that fascinates Tim.
- Modern celebrity spirits like Ryan Reynolds' gin and Clooney's tequila succeed because they're actually good products, not novelty cash grabs like 80s endorsements.
- MrBeast and creators like him will build multi-billion-dollar companies by understanding their audience and playing the long game with patience.
- ExpressVPN ad: a virtual private network that stops companies from stealing your data, mining information, and selling it to the government and advertisers.
- Using ExpressVPN anonymizes your identity through encrypted secure servers so ISPs cannot track your online activity across all your devices.
Evan WilliamsMrBeastExpressVPNJack DorseySarah BlakelySpanxRyan ReynoldsBeast Burger+7 more
- 3 min
They riff on whether a scandal-plagued company like Weinstein's can rebuild by 'just making great movies,' spinning into a bit about Skechers making a Nazi boot, and Gary's philosophy that the business world is abundant and no one is stealing your fans.
7moments
- Tim discusses how the Weinstein Company could make a comeback by going back to basics and making great movies.
- Adidas and BMW were Nazi-driven companies, so Tim proposes Skechers could do a Nazi boot as a business strategy.
- Tim believes a Nazi boot is genuinely in Skechers' best business interest to revive the brand.
- The world is fundamentally abundant and there's nobody taking fans or success from you in entertainment.
- Joe Rogan showed that by sharing and collaborating, creators actually help each other succeed.
- Tim explains his competitive nature using the Jets as an example—he hates when players give love to opponents after losing.
- In real business pitches, Tim doesn't get angry when losing because he doesn't believe anyone's taking anything from him.
- 2 min
Gary says he never cared about buying things, only experiences like family vacations, and that his real driving curiosity is finding out how great an entrepreneur he actually is.
4moments
- Guest bought custom Jets jerseys of random players nobody knew when he first started making money.
- Tim asks what he buys now; guest says he doesn't like stuff, prefers vacations and experiences with family.
- Guest wants to know how great of an entrepreneur he is before he dies.
- Tim notes guest loves the game so much he wants to give back to it.
JoeLogan Roy
- 4 min
Gary talks about loving to give love to up-and-comers like OGs do for young comics, then has employees Dustin and Sean tell their own hiring stories live on the mic.
8moments
- Tim describes his fascination with established comedians giving encouragement to up-and-coming performers at clubs.
- Gary talks about mentoring people in his businesses and wanting to leave a legacy that provides value to others.
- Tim asks how Gary spots talent, bringing up the idea of discovering exceptional waiters or bartenders and hiring them directly.
- Gary describes the intense hunger he sees in people he hires, noting they have a certain terrifying look in their eyes.
- Dustin explains he applied twice to Vayner Media, got rejected both times, then was contacted four months later by a director.
- Sean applied twice without hearing back, then started gaining traction on TikTok before someone reached out offering work editing Gary's content.
- Sean describes being depressed during COVID, bombing a bank interview, discovering Gary's blog post about the creative industry and applying online.
- Gary says he doesn't intimidate people in interviews, only with his direct reports and C-suite conversations.
Laugh FactoryVaynerGaryDustin
- 4 min
Gary admits hiring is largely intuition and guesswork, then pivots into advising Tim to post more on LinkedIn and explains 'contextual creative' — tailoring content differently for each platform and city, just like a comedian adjusts jokes by room.
7moments
- Tim argues that hiring is fundamentally guessing, though experience makes you better at it.
- He describes mishiring people constantly and laughing at how bad recent hires have turned out.
- The key to good employees at his company: avoiding cynicism and not being afraid, since the doors are open and communication is unlimited.
- Tim suggests doing more content on LinkedIn, since his thoughtful comedy would work well there clipped and properly framed.
- Every platform requires different creative strategy—TikTok, YouTube Shorts, and Twitter each demand their own approach.
- Comedy changes city to city and country to country; Tim tailors his sets with location-specific jokes like Josh Allen references in Buffalo or footy jokes in Australia.
- Understanding contextual creative—tailoring content to each platform where you're actually distributing it—is the single most important thing that can advance a career or business.
LinkedInTikTokYouTubeTwitterCooper's beerJosh Allen
- 2 min
Gary predicts every business will eventually have an NFT strategy the way every business has an app, and speculates that in 16 years Tim will do 200 VR shows a year without traveling, living in a floating pod.
6moments
- Tim explains crypto winter is when B-players get smoked out after C and D players are already dead.
- NFTs like CryptoPunks have collapsed in value, dropping from their peaks to around 80k.
- Every business is going to eventually have an NFT strategy, inevitable within the next decade or two.
- The technology will work for every business, but not every project becomes Bored Ape—it's about the tech, not collectibility.
- Tim says he's actually excited about doing virtual events in 15 years when VR is at full scale.
- His prediction: in 16 years with full VR, he'll live somewhere and do 200 shows a year without traveling.
cryptocurrencyNFTsCryptoPunksmetaverse
- 4 min
They riff on Austin's barbecue-and-lesbians reputation versus New York, Gary's refusal to ever live there or in L.A./Miami/Detroit/Florida, comparing New York loyalty to Jets fandom, and Tim tells a story about a delusional double-decker tour guide named Bernie loyal to the Bronx and Yankees.
7moments
- Everyone's saying Austin is the next thing, but Tim argues it's actually a dump and the people moving there are insane.
- Tim declares he will never live in Austin, LA, Detroit, or Florida—he's staying in New York.
- The deciding factor for staying in New York: the Jets.
- Tim recalls a tour guide named Bernie in the Bronx who refused to move despite being broke, staying only for the Yankees.
- New York has everything—it's crowded, full of people, and there's nothing Austin has that the city doesn't already offer.
- Tim moved to LA because you have to get close to the devil in the entertainment business before he eats your soul.
- As a kid, Tim was drawn to cynical, sarcastic adults who smoked outside and said rude things—he wanted to do that for a living.
New YorkAustinNew York JetsYankeesLos Angeles
- 4 min
Tim describes being drawn as a kid to cynical, sarcastic adults smoking cigarettes and being 'total pieces of shit,' framing his worldview around finding humor in darkness, and Gary claims a kinship with that framework, joking about a 'Racist Rhino' VeeFriend.
8moments
- Tim explains how framing horror and sadness in a funny way becomes a survival mechanism and perspective shift.
- He draws a kinship between himself and Sam Bankman-Fried based on their shared framework of finding humor in heavy situations.
- Tim pitches a concept: a racist rhino character from 1957 who isn't malicious, just a product of his ignorant time.
- Hitler's hypothetical presence on Twitter today would likely be prevented by the speed of information flow, not content moderation.
- Tim argues that asking tech companies to make subjective moderation calls is practically impossible and fundamentally a government regulation question.
- Satire and sarcasm suffer on social media because tone of voice and live performance context disappear in text.
- He contends most people actually do understand intent, but cancel culture practitioners are tone-deaf to it.
- Removing intent and context from conversation is what creates genuine cultural challenges.
- 2 min
They discuss how social media strips away tone and intent making satire hard to parse, and debate whether government should be forcing tech companies to make subjective moderation calls.
5moments
- Tim describes himself as simple, high-energy and pumped, but argues none of this stuff actually matters.
- The real reason people get upset is because they think there's somebody important behind the outrage.
- Prince's death culturally meant something, but a week later the world moves on and everyone's walking around offended as if they matter.
- Asked what advice he'd give the Trump brand to turn things around, Tim says it's complicated.
- Tim's opening question to every client is what they'd like to accomplish—but for Trump, that ship has sailed.
Donald TrumpPrince
- 3 min
Gary gives mock PR advice for the Trump brand, argues algorithms just serve ads rather than conspiring against people, and pivots to blaming bad parenting rather than platforms, praising the Kardashian/Jenner family's business success and closeness.
8moments
- The algorithm responds to what you want to see—it's just selling ads, no different than how Seinfeld made NBC money.
- Tim argues we should have a more modern conversation about parenting instead of blaming platforms for what kids see online.
- Chris and Caitlin turned their family into a multi-billion-dollar business that cheapened and destroyed Earth.
- It's insane how much the Kardashian siblings love each other—if his siblings were billionaires, he'd love them even more.
- Tim thinks she should be the governor of California because she's a hard worker.
- Tim considers running for office somewhere, saying it would be no different than showing up when a friend asks.
- Kansas is rough but you could do what you want there; it's the place to run for governor or make big moves.
- Miami is warm, has the Coke Paradise vibe, and is becoming the crypto hub and future of something big.
- 3 min
Gary mocks New York friends who fled to Miami during COVID and quietly moved back, reaffirms New York's supremacy over Austin/Miami/L.A., discusses his easy sleep, and closes with advice about timing and humility aimed directly at Sam Bankman-Fried.
6moments
- Tim's New York friends moved to Miami post-COVID claiming they'd stay, but they all came back; he won side bets on their delusion.
- Miami, Austin, and other cities are great to visit, but compared to New York they don't exist—New York is the greatest city in the world.
- Tim sleeps like a light, straight through seven to eight hours without waking up or needing to piss, no stress.
- Advice for people with an idea that hasn't worked: timing might be off, or you might need to bring in a partner rather than going solo.
- Fifty percent of something meaningful is better than a hundred percent of nothing; humility is a huge factor in success.
- Sam Bankman-Fried, if you're listening, look in the mirror and be honest about whether you can execute your idea or need help.