Episode 119 · The GaS Digital / Ray Kump Era
Rich Cunt with Hailey Sacks
with Hailey Sacks
Oct 26, 2018 · 1:08:26 · 25 segments, 177 moments indexed
- 1 min
Opening music and show title announcement, no substantive talk yet.
1moment
- 0:02Show intro: Tim Dillon Is Going To Hell with Tim Dillon and Ray Kump
- 1 min
Ray's Leg Infection and Cellulitis Saga
#Tim welcomes Ray Kump back after a flu and introduces a lingering leg infection (cellulitis) Ray developed, with Tim mocking his doctor visits and mobility issues.
4moments
- 0:31Ray had the flu last week and developed a leg infection that he still has.
- 0:50Tim explains the infection is cellulitis on his shin, caused by a weakened immune system from the flu.
- 1:02After six days of antibiotics in a ten-day treatment, the infection wasn't going down, so he went back to the doctor.
- 1:14Ray's shin has become hard and barely mobile, like a shell.
Ray KumpBrendan Dassey
- 2 min
Planning the Halloween Seance with a Witch or Warlock
#Tim discusses next week's planned Halloween seance episode, references returning guest Francis James and his 9/11 nuclear detonation theory, and asks the audience to recommend a real witch or warlock rather than a mentalist.
4moments
- 1:35Tim announces they're planning a Halloween seance for next week, hopefully with Dan St. Germain and Francis James.
- 2:09They need to find a witch or warlock to act as a medium and help contact the dead for the seance.
- 2:30Tim rules out hiring a mentalist—he doesn't want someone who bends spoons or moves metal and impresses no one.
- 2:47What they want is someone genuinely dark who can go into hell and bring back figures like Allen Dulles for an interview.
- 4 min
Haley (Mrs. Dow Jones) is introduced and grilled about her wealthy upbringing — doormen who are ex-military or drug dealers, drug use among rich UES teens, absent jet-setting parents, rehab culture, and a friend who goes to chic rehabs and hangs with Scott Disick.
11moments
- 3:10Tim notes that Haley's brand is built on being wealthy and leaning into it.
- 3:28Upper East Side doormen serve as protection against street violence, and many of them have military backgrounds.
- 3:54Doormen in fancy buildings were hiring ex-military personnel and also dealing drugs on the side.
- 4:08Haley admits she was a drug user in high school, though just weed compared to the pills and cocaine other Upper East Side girls were doing.
- 4:30Tim points out that wealthy girls who do cocaine young will have to give it up later, and asks about drug prevalence in the upper class.
- 4:55Rich girls would get in minivans on Madison Avenue to buy dime bags rather than venture to the Bronx for drugs.
- 5:18Tim observes that wealthy parents are usually absent, though Jewish families are different in that regard.
- 5:51The lifestyles of neglected rich kids either end when money runs out or when they end up in rehab.
- 6:27Haley describes a wealthy friend who cycles through exclusive rehab facilities and sends photos from treatment, with therapy that suggests horseback riding as a cure.
- 6:47Tim notes that rich kids return to New York from celebrity rehab, decide drugs are necessary to avoid boredom, and use again.
- 6:58Tim begins asking about the differences between rich Jewish kids and other wealthy children.
Scott DisickHaley
- 3 min
Discussion of how wealthy kids avoid being bums via fake startups, girlboss brands, or legitimate jobs in finance and PR, plus Haley's insight into high-stakes finance culture and her sister getting shingles from stress at a bank.
9moments
- 7:13The new low thing rich kids do is having a startup, especially girl bosses where you can't tell what the profits actually are.
- 7:26Tim's bit: you come back from Coachella coked out, your dad says you should have a stapler, gets you an office with a COO to actually run it.
- 7:37Rich parents create bullshit jobs to safeguard their own image, but the kids who go into finance and PR aren't actually in bullshit jobs.
- 8:07Instead of being bums, a lot of these people just have sobriety issues and mental illness.
- 8:30Finance is a high-stakes environment where you're playing with people's money and mistakes aren't tolerated, regardless of who your dad is.
- 8:49His sister got shingles from stress working at a major bank because the pressure was so intense.
- 9:21Tim knew guys in the mortgage industry from Orange County making tens of millions, but they were cowboys, not Upper East Side society people.
- 9:57There's total separation in childhood—prep school kids and WASPs existed in a completely different world that he didn't encounter until college.
- 10:09The guest didn't even meet WASPs until college, which people don't understand about class segregation.
startup cultureWeWorkUpper East SidefinanceGoldman SachsOrange County, California
- 3 min
Tim and Ray contrast their working/middle-class Long Island upbringing (no Thai food, no prep school friends) with Haley's rarefied world, including her anorexic mother's eating habits and how rich wives stay thin to keep their husbands.
10moments
- 10:12Tim didn't have Thai or Indian food growing up in his segregated neighborhood.
- 10:23Ray's anorexic mother couldn't eat normal family meals, just unlimited vegetables and a little protein.
- 11:00Tim explains that maintaining extreme thinness is how wealthy Upper East Side women keep their benefactors.
- 11:39If a rich woman gains weight, she's out of the relationship entirely unless she gets sick.
- 11:53Rich people don't like disease and actively hide sick family members away.
- 12:09Tim speculates about the recent trend of female actresses getting diagnosed with serious illnesses.
- 12:21Having a disease is actually smart for a celebrity's career, opening up the charity circuit.
- 12:34Tim argues Charlie Sheen was smart to get AIDS but failed to capitalize on it properly.
- 12:50Charlie Sheen recklessly transmitted HIV to multiple people, unlike other celebrities who've had the disease.
- 13:11Charlie Sheen's HIV narrative is not compelling, though having AIDS is vintage and you don't see it anymore.
Charlie SheenSalma BlairMichael J FoxArthur Ashe
- 2 min
Illness as Social Currency: Salma Blair, Michael J. Fox, Charlie Sheen's AIDS
#The group riffs on how the wealthy view disease as a weakness unless it can be monetized for sympathy, joking about celebrities using illness (MS, Parkinson's, HIV) as a career or social move, with Charlie Sheen's HIV disclosure as the prime example.
6moments
- 13:40Real estate is the obvious way to make wealth, though it can be a productive family enterprise.
- 13:58Tim describes a sector of new girl boss creative brands making successful businesses.
- 14:11Discussion of Dani Beckerman's viral cake-in-a-jar Instagram business model.
- 14:23Tim just wants cake, getting distracted by the jar gimmick itself.
- 14:35Asian viral dessert trends are theatrical and overrated, none of them actually good.
- 14:51Nobody in these business circles ever talks about the Flint water crisis or similar real problems.
Dani Beckerman
- 2 min
Rich Girl Startups and Cake-in-a-Jar Instagram Grifts
#Talk turns to trust-fund entrepreneurs and viral dessert trends like 'cake in a jar' and Asian shaved ice, before Tim needles the group about whether anyone in that world thinks about Flint's water crisis.
5moments
- 15:04Tim questions whether anyone has social conscience, noting everyone voted for Hillary
- 15:27Tim pushes back on the idea that he's a social activist, positioning himself as a man of the people
- 15:52Tim contrasts his own bottled water consumption with working-class drinking habits
- 16:10Rich people have weaponized philanthropy and use charities for personal betterment rather than genuine good
- 16:28The narrative matters in anything, but especially in charity work
- 2 min
Weaponized Philanthropy and the Rich's Selective Charity
#Tim argues rich people's charity work and causes (like Erin Brockovich-style activism) mostly serve their own image, while Haley defends that charity needs a personal narrative; talk of a possible Big Brothers Big Sisters volunteer stunt for the show.
5moments
- 16:50Tim is on a junior board and considering volunteer work like Big Brothers Big Sisters or hospital visits.
- 17:05Rather than actually volunteer, Tim pitches making a TV show about himself doing volunteer work instead.
- 17:18Tim's logic: a successful TV show about volunteering helps more people than actually working with two kids with cancer.
- 17:29Framing the show as a way to teach the world that helping is fun and funny, making it sound like genuine public service.
- 18:00Tim mentions getting back with the Boy Scouts as another giving-back option he's considering.
Shonda RhimesBoy Scouts
- 2 min
Haley describes her actual junior board volunteer work (pumpkin painting with men in foster care) and a joke about painting for the infamous 'that girl' hoax victim, before the group jokingly declares themselves capitalists turning into anarchists.
6moments
- 18:25Tim is volunteering this Sunday to paint pumpkins with underprivileged men in foster care.
- 18:50The program includes teaching participants about the Me Too movement.
- 19:24Tim describes the trajectory: starting as capitalists but ending as members of the Black Block.
- 19:45The real problem isn't that Tim and his guest are capitalists—it's that the people in their circle aren't.
- 20:00They embrace socialism when government bailouts save their companies but oppose it for workers.
- 20:15When countries nationalize resources that Western powers financed colonization to control, capitalists run to the government demanding intervention.
- 3 min
Ray's Anti-Oligarchy Rant: CIA, Federal Reserve, and Regime Change
#Ray delivers an extended political rant about how the wealthy use government and institutions like the CIA and Federal Reserve to enrich themselves while calling foreign nationalization efforts 'communist,' tying it to why migrants flee US-destabilized countries.
8moments
- 20:40CIA overthrows governments in Iran and elsewhere because they don't want to share the oil.
- 21:00Ray's ideal world: the wealthy aren't penalized for success, but can't use government to entrench power.
- 21:39The Federal Reserve functions as a tool wielded by shifting powers to benefit a select group.
- 21:50Tim argues the CIA, formed by lawyers to protect client assets, operates in shadows overthrowing democratically elected governments for multinational corporations.
- 22:25This pattern has happened across Latin America and South America for a very long time.
- 22:45When politicians claim migrant caravan countries are the most violent on earth, they ignore U.S. involvement in destabilizing those regions.
- 22:59Tim distinguishes between entrepreneurial wealth creation like PT Barnum or Steve Jobs versus systemic exploitation through currency manipulation and strip-mining entire countries.
- 23:30The economy is in a big bubble right now, and not everyone has a nest egg to fall back on.
CIASteve KingSteve JobsPT Barnum
- 3 min
Haley talks about running a positive-finance brand amid bubble fears and recession gallows humor, then the group discusses Hillary Clinton's 2016 loss, her reaction to Gaddafi's death, and a wildly wrong claim about 100 million new voters.
8moments
- 23:50Tim asks whether finance content stays fun and flirty if central banks collapse and people are eating each other in the streets.
- 24:32Everyone relies on gallows humor during recessions, Tim says—Morgan Stanley guys and Goldman girls need something to laugh at when things fall apart.
- 25:01Tim was a Hillary Clinton fan, went to a party with custom cookies bearing her face, surrounded by girls and gays ready to celebrate.
- 25:18Hillary Clinton laughed as Muammar Gaddafi was sodomized to death.
- 25:44Tim hasn't voted since casting a ballot for Bush once and Obama once, claiming New York voting doesn't matter anyway.
- 26:00New York's assembly is conservative upstate, but Tim suggests urban votes are functionally irrelevant to state outcomes.
- 26:17The claim of 100 million new voters is mathematically impossible—that's a third of the entire U.S. population.
- 26:37Hillary Clinton's head is just memes going through; she doesn't have thoughts, only memes.
- 4 min
Haley critiques Tim and Ray's fashion sense (button-downs, beards, 'husky guy' body type), riffs on riot-chic handbags and post-apocalyptic fashion trends, and recalls getting punched at the Women's March.
9moments
- 26:55Haley diagnoses Tim and Ray's fashion problem as lack of confidence and discomfort with their own style.
- 27:14Tim jokes that his self-confidence would tank rather than spiral up if he took fashion advice.
- 27:34Haley suggests Tim shave his beard, but he argues it's the only thing providing contour to his face.
- 27:58Ray defends his button-down style while admitting Tim calls him a slob.
- 28:23Haley describes dressing for their body type, referring to them as husky, rugged guys.
- 28:41Fashion is becoming playful and funny rather than serious, Haley explains.
- 29:09Tim calls Haley's pocketbook post-apocalyptic, asking if riots and civil unrest are where fashion is heading.
- 29:33Political influence is showing up in fashion trends, Ray observes.
- 29:50Ray notes the pocketbook is heavy enough to use as a weapon during a riot.
- 4 min
Haley brands Tim as authentic American-royalty Ralph Lauren energy and Ray as a wild, John C. Reilly-esque eccentric character, leading into talk about Will Arnett dates, ideal wealthy first dates at the Four Seasons pool room, and dating across class lines.
9moments
- 30:31Tim's style icon is Ralph Lauren—everything polo, American royalty, patriarchy, authority, and comfort.
- 30:51His Chevy Suburban, though heavily financed and repossessed, epitomizes the brand he's created.
- 31:03Ray's persona compared to late Bobby Fischer—a genius in a park making controversial statements about Israel.
- 31:16The Bobby Fischer type: animals understand him, carries a flip phone instead of an iPhone, defecates in gardens that rich people love.
- 31:55Tim on LA actors: they all suck, they're 45 years old playing in bands and trying stand-up.
- 32:19What makes a perfect date for a wealthy woman—a black car and the Four Seasons pool room, where you have caviar and champagne but don't necessarily eat.
- 32:53Starting a relationship at an upscale venue like the pool room creates anticipation for what comes next; starting at a dive bar leaves nowhere to go.
- 33:33The question of whether a wealthy woman should take a blue-collar guy out and show him experiences, or if class differences make dating impossible.
- 34:07Dan Soder's relationship with a woman of lower financial status didn't work out—wealthy people typically don't date down.
- 4 min
Discussion of how the wealthy marry within their class, prenup dynamics revealing net worth, a friend's mortgage-guy daughter who secretly married a plumber, and a story about student loan debt scaring off suitors.
9moments
- 34:32Tim probes whether someone could date outside their class and watches them initially deflect before admitting the real requirement is wealth, not love.
- 35:15Closed ranks in rich families mean outsiders don't get in; stability and money matter more than following your heart.
- 35:59The hypothetical of bringing someone poor home—doorman calls police, the whole class collision plays out.
- 36:19Rich people don't meet those beneath their station except through dating apps, where relationships fizzle after five months when reality sets in.
- 36:40Wealthy women have to be cold because following your heart can impoverish you, so they guard against it.
- 36:58Most married couples stay within their class; even the rich people he knows who married outside their circle ended up not living rich lives.
- 37:39Tim asks about the prenup on a marriage between a multihundred-millionaire and a plumber—the guy signed but then forgot about it.
- 37:53Walking down the aisle means you know exactly what both people are worth down to the dollar, which shapes the whole dynamic.
- 38:03Student loans function as a dealbreaker in dating; a friend won't marry a woman with 200 grand in debt because he can't take that on while buying a house and raising kids.
- 3 min
Haley praises the show and jokingly pitches herself as a co-host, debates whether Tim is a 'conspiracy theorist,' and they compare the show's Twitter-vs-Insta audience and lack of a housekeeper.
8moments
- 38:27Haley says she's a huge fan of the show and feels like she's inside a dream listening to it.
- 39:06Tim notes that everything Haley says sounds ridiculous until you think about it and realize it's not wrong.
- 39:29Tim insists he's not a conspiracy theorist, rejecting the label as part of his brand.
- 39:45Haley describes Tim's approach to questioning things like asking 'What happened in 2008?' at the dinner table, which gets labeled as conspiracy thinking.
- 40:21Tim explains that wealthy families don't have rabbis who travel with them and give special blessings on lobster to make it kosher.
- 40:44Rich kids get in arguments over the same things as other kids—boys, other typical childhood drama.
- 40:59Haley transferred from Dalton to the Upper West Side partly because having two sisters already in the same high school created too much family overlap.
- 41:30Haley got bullied at Dalton, and Tim responds by noting how great it is when you're rich and bullied—your parents just send you to a different school.
Stanford Business SchoolLloyd BlankfeinDaltonUpper West SideDonald Trump
- 3 min
Haley recounts being bullied at Dalton and transferring schools, contrasted with Tim's working-class inability to simply switch schools, plus a bit about her old bully now succeeding at Goldman and Stanford but still single.
9moments
- 41:49Tim says hitting the bully was justified because the psychological warfare was worse.
- 42:10The bully turned out successful, but her real downfall is that all her friends are married and she isn't.
- 42:22Tim suggests the bully's lack of engagement stems from prioritizing career over love life.
- 42:52Guest claims to be a feminist, comparing herself to Lena Dunham.
- 43:08She still tags the former bully in memes about bullies and meets up with her for financial advice.
- 43:23The bully now works at Goldman and attends Stanford Business School.
- 43:34Tim asks what it takes to succeed at an elite institution like Stanford or Goldman.
- 43:47Guest emphasizes that success isn't about where you come from but where you're going.
- 44:17Tim says Dick Fauld would have loved the guest.
- 5 min
Tim explains his success is driven by addiction rather than ambition, and the group discusses how 'alternative' comedy and culture (Broad City, Echo Park) have actually become mainstream and safe.
10moments
- 45:28Financial success has never motivated Tim in life, or any type of it.
- 45:45Tim attributes his drive to addiction rather than moral choice—he gets addicted to things like drugs and comedy.
- 46:16Tim's brand of comedy is genuinely alternative, but that's why it's not marketable.
- 46:30What people call alternative comedy is actually relatively mainstream now.
- 47:11Urban Outfitters co-opts supposedly alternative things to seem cool and edgy without actually being cool and edgy.
- 47:33Being pro-gay and pro-women are not controversial positions and shouldn't be.
- 47:48Tim and Ray discuss political assassinations, human trafficking, and blackmail—topics nobody really engages with in a meaningful way.
- 48:01To be marketable, Tim would have to dumb down the material and remove nuance.
- 48:21Tim advertises gambling websites and dick pills on his show.
- 48:43Proposal for a conspiracy book marketed for the holidays with Tim's illustration integrated into the design.
- 3 min
Haley pitches merch ideas for the show including a conspiracy-themed holiday book and knife merch, then the conversation drifts into a food tour of fancy NYC restaurants like Felidia, Le Bernardin, and Daniel.
8moments
- 49:01Tim headlines comedy shows but never sells merchandise.
- 49:25Tim imagines what appetizers would be at a restaurant with the hosts.
- 49:50Tim would make spanner capita as a signature dish if he owned a restaurant.
- 50:25Felidia does charred octopus and octopus salami that Tim finds interesting.
- 50:46Tim identifies as a steakhouse guy who prefers shellfish and steak with big tables and martinis.
- 51:03Eighth-grade tasting menu at La Brebe with every course still memorable decades later.
- 51:27Danielle and Oreo, a Charlie Palmer restaurant in a townhouse on the Upper East Side near the museum.
- 51:55Tim used to get high and go to a Mongolian barbecue buffet where you pick meat with tongs and they cook it on stone.
La BrebeFelidiaCharlie PalmerLydia BastianichaDanielle and Oreo
- 5 min
Sushi Omakase, Nazi Fitness Jokes, and Booking Big Business Guests
#The group talks favorite sushi spots and spending habits on omakase, jokes about Nazis all being fit, and laments that real business figures (like a NYC realtor) won't come on the show while Steve Bannon and Ann Coulter would.
9moments
- 52:28Tim explains his obsession with omakase and sushi, planning to go the next day.
- 52:54He recalls going to Walk and Roll, an all-you-can-order sushi spot that deliberately serves rotten fish on the third order to make customers leave.
- 53:12Tim describes eating three or four cloves of garlic while sick with the flu and throwing up in the bathroom.
- 53:33The guest advises Tim that the show's branding could improve with digital content—subtitled clips, weekly visuals—rather than just static logos.
- 54:38Tim says he tried to book big business guests, including realtor Dolly Lenz through her daughter, but they won't come on the show.
- 55:17Mainstream figures like Ann Coulter and Steve Bannon will appear, but establishment media figures from the New York Times refuse, treating podcasting as beneath them.
- 55:59Tim jokes that they can't go Nazi with Fox News, then claims Nazis are all great-looking because they practice Nordic fitness.
- 56:29He notes the show is willing to go hard communist if needed, just trying anything to grow, and considers new advertisers like sex toy companies.
- 56:49The guest notes business people really won't come on the show, which Tim acknowledges is unfortunate.
Steve BannonAnn CoulterDonald TrumpNew York TimesFox NewsMasaHerman GoeringDolly Lens+1 more
- 3 min
Haley admits to a self-described 'fetish' for wanting financial independence despite her wealthy safety net, and the group debates whether $100-380 dinners and omakase splurges are normal for her.
8moments
- 57:25Haley plugs her social media handle, Mrs. Dow Jones, and pitches ideas for a follow-up with Ray and Tim.
- 57:37Tim dismisses the omakase plan by calling everyone involved a psychopath.
- 57:52Conversation shifts to Sushi Saki and the cost of high-end sushi dinners.
- 58:31Tim mentions spending $380 at a steakhouse after going shellfish crazy with crab legs and lobster cocktails.
- 59:03Tim justifies expensive dinners by saying he works hard and deserves to eat well.
- 59:33Haley reveals she gets angry if she spends over $100 on dinner because she's trying to become financially independent.
- 59:45Tim addresses her financial independence fetish and asks why it matters to her.
- 59:58Tim argues that even if she achieves financial independence, she'll never have an interesting story to tell about it.
Sushi SakiMrs. Dow JonesGotham
- 3 min
Haley tells a story about pulling a knife on the nanny as a kid and her father's threat to send her away, leading into talk about Park Avenue real estate, Tribeca vs. Upper East Side status, and boarding school culture including a Brett Kavanaugh aside.
6moments
- 1:00:34Tim argues the only way to feel truly alive as a rich kid is to get your parents to cut you off completely.
- 1:00:58Bringing a crack pipe onto the couch would guarantee parental exile—no accessories needed, just Ray himself walking in the house.
- 1:01:47Guest brandished a knife at his sister during a dinner argument and was threatened with boarding school exile by his father.
- 1:02:25Tim notes that young people repeating the same Park Avenue life cycle across generations, with Tribeca as the hot alternative neighborhood.
- 1:02:54Upper East Side childhood involves a specific luxury routine: body by Simone, lunch at Bubbies, highlights, and inevitably losing an attached nanny to deportation.
- 1:03:10Wealthy WASP families send their children to boarding school at age 14 as a matter of course, with kids knowing early they'll be shipped away.
TribecaBergdorf GoodmanPark AvenueWest VillageAnguillaBrett Kavanaugh
- 2 min
Discussion of casual homosexuality assumptions at elite boarding schools, Haley's Upper West Side upbringing versus the 'cool downtown girl,' and her complicated admiration/fat-shaming take on Lena Dunham.
8moments
- 1:03:35Questions about casual homosexuality at boarding schools and private schools among the wealthy.
- 1:03:51Tim says the gay guy at school always seemed straight and would try to hook up with people.
- 1:04:10Description of the cool downtown girl archetype: adorexic, leather jacket, cigarettes, lived near Sarah Jessica Parker.
- 1:04:27Tim brings up Lena Dunham and Jemima Kirk as examples of that downtown cool world.
- 1:04:38Guest dismisses Lena Dunham as trite, lacking the metal force to be a true superstar.
- 1:04:57Tim mentions dating a girl from Flanders who went to Marymount, an Upper East Side school.
- 1:05:18Tim's observation about chubby girls with hot boyfriends breaking up and wondering if the boyfriend was pursuing a fetish.
- 1:05:30Guest admits to fat shaming and blames it on how she was raised.
Lena DunhamLady GagaSarah Jessica ParkerJemima Kirk
- 2 min
Closing riff on why Tim hasn't been invited into wealthy social circles despite Netflix and Comedy Central specials, and the two paths in (extreme hotness or extreme success) with a joke about marrying for love the second time.
5moments
- 1:05:44Tim thought he'd gain rich friends after Netflix and Comedy Central specials, but it never happened.
- 1:06:00Selling out arenas is the requirement for being invited onto yachts by the wealthy.
- 1:06:11Rich people don't want anyone who needs what they have—they're looking for self-sufficient individuals.
- 1:06:42Different standards apply to women—a hot woman can date a rich man regardless of background, but men need more going on.
- 1:07:08Tim cancels Comedy Cellar dates due to scheduling conflict and directs people to see Bobby Kelly instead.
- 1 min
Tim announces a scheduling conflict causing him to miss a Broward show (recommending Bobby Kelly instead), plugs subscribing and rating on iTunes, upcoming NY Comedy Festival shows, and Haley and Ray plug their socials before signing off.
2moments
- 1:07:26Subscribe to Gas Digital with promo code, and follow Tim on Instagram.
- 1:07:44Live shows sold out for New York Comedy Festival November 7th and 8th.