Episode 3 · The GaS Digital / Ray Kump Era
Tough Love
Jul 26, 2016 · 1:02:08 · 21 segments, 136 moments indexed
- 1 min
Cold Open: Special Sunday Taping Announcement
#Tim explains this is a special Sunday-recorded episode being released Tuesday because he'll be out of the country, joined by co-host Ray Kump.
2moments
- 0:00Tim opens a special edition of Going To Hell
- 0:51Ray Kump joins as co-host
- 1 min
Tim thanks listeners for the show's positive reception, mentions download numbers around 100-115, and pushes the GaS Digital Network subscription with promo code HELL, name-checking Legion of Skanks, High Society Radio, and Part of the Problem.
4moments
- 1:05Tim Dillon is going to hell — literally, recording an episode today on Sunday for Tuesday release.
- 1:40The show debuted between 100 and 115 iTunes rankings, which he wants to maintain.
- 1:55Subscribe to GAS Digital using promo code 'hell' to access multiple shows for $6 a month.
- 2:20Tim tells people to grow up and get a job if they think $6 a month is too much money.
- 1 min
A Golden Age of Chaos: Race Wars, Coups, and Nazi Salutes
#Tim riffs on how every week now brings new political catastrophe compared to the relatively calm 90s, then introduces Laura Ingraham's controversial hand gesture at the RNC that looked like a Nazi salute.
4moments
- 2:32Tim notes that podcasting now is amazing because every week something significant happens globally—race wars, terrorist attacks, failed coups, Nazi salutes.
- 2:47Podcasts in the 90s would have been dull compared to now, since that era was a time of relative peace and tranquility globally.
- 3:14Tim mentions that a nominee for one of the political parties has made a Nazi salute, then asks about Laura Ingraham's Nazi salute specifically.
- 3:42The Heil Hitler salute can look similar to the Black Power salute if you don't look closely enough.
- 2 min
They break down whether Ingraham's gesture was an awkward save after a Nazi salute, then pivot to WikiLeaks' release of DNC emails showing Debbie Wasserman Schultz and the DNC scheming against Bernie Sanders, including a plan to attack his lack of religion in the South.
4moments
- 4:11Laura Ingraham appeared to do a Nazi salute before waving, raising the question of whether it was an instinctive gesture she tried to cover up.
- 4:44Debbie Wasserman Schultz, head of the DNC, faced accusations of rigging the primary against Bernie Sanders.
- 5:16WikiLeaks released emails showing the DNC planned to attack Sanders based on his religion and atheism.
- 5:42The DNC strategy involved telling Southern voters Sanders was an atheist who believes in nothing, rather than emphasizing his Jewish heritage.
Debbie Wasserman SchultzJulian AssangeHillary ClintonBernie Sanders
- 2 min
Charismatic Fundamentalists: Islamic Preachers, Joel Osteen, and Tent Revival Charm
#Tim describes being surprisingly entertained watching Islamic fundamentalist preachers on YouTube, comparing their charisma to Christian tent preachers and Joel Osteen, and joking he could have been a great tent preacher himself.
4moments
- 6:10Tim watched Islamic fundamentalist preachers on YouTube and found them surprisingly charming and gregarious.
- 6:41One preacher was talking about flying first class, which wasn't the doom-and-gloom content Tim expected.
- 7:00Fundamentalist appeal spans across religions—Christian tent preachers and preachers use the same charismatic playbook.
- 7:18Tim says he would have made a great tent preacher if comedy didn't work out.
Joel OsteenIslamic fundamentalist preachers
- 2 min
Tony Robbins Documentary, Nepotism, and Dynasty-Proof Comedy
#Tim praises the Netflix Tony Robbins documentary and his motivational methods, then gets into a debate about nepotism in music (John Hiatt's daughter) versus comedy being relatively "dynasty-proof," name-dropping Jason Reitman and Rain Pryor.
6moments
- 7:40Tim recommends watching the Tony Robbins documentary on Netflix and says he's always liked Robbins.
- 8:08Tony Robbins as a motivational speaker cuts through bullshit to the heart of people's issues in massive convention settings.
- 8:28Comparing Robbins to comedians who can connect on a huge level and fill theaters—only about 25 stand-up comedians can do this consistently in America.
- 8:43Tim admits he can't fill theaters consistently and jokes that Ray can fill courtrooms consistently.
- 9:05Tim notes that Tony Robbins's son is also a motivational speaker, which makes the whole thing start to look like a racket.
- 9:19Once you see Robbins's origin story and learn his junior got the gift too, it looks suspicious—like nepotism passed down as magic.
- 2 min
Motivational Speaker Dynasties and Broke Life Coaches
#They wonder if any famous preacher's kid became a huge success, question whether motivational speaking is a hereditary racket, and joke about life coaches who are personally broke or getting evicted while still selling success.
5moments
- 9:30Motivational speaker seminars cost around $5,000 and welcome anyone's conception of God—bring your own.
- 9:54Tim hates opening acts at concerts, even when the headliner is John Hyatt, a musician he respects.
- 10:19Nepotism in finance, law, and politics doesn't bother him, but something about a musician's kid opening for the parent bothers him personally.
- 10:40Jason Reitman directing Juno as a successful example of nepotism in film, though the pattern isn't universal.
- 10:56Comedy seems uniquely dynasty-proof because success requires actual work and can't be handed down like other industries.
John HyattJason ReitmanPaulie ShoreRain Pryor
- 1 min
Tony Robbins' Method and the Value of Getting Screamed At
#Tim argues Robbins' aggressive, in-your-face style genuinely helps people because modern relationships (Facebook, Twitter) are shallow, and that being forced to confront your issues in a room full of strangers has real value.
4moments
- 11:10Tim argues that comedians being constantly judged is what he values about the art form.
- 11:22In the arts especially, Tim believes in earning your keep rather than coasting on family connections.
- 11:38Tim acknowledges rich kids do comedy too, but argues against getting unearned stage time just for touring with your dad.
- 11:50Tim prefaces a self-deprecating admission: his father sold office equipment, and he did the same work later in life.
Tony RobinsonJohn Hight
- 4 min
Selling Subprime Mortgages in 2009 with Brian Tracy Tapes
#Tim tells an extended story about working mortgage sales post-crash in 2009, his abrasive boss forcing the team to listen to Brian Tracy and Zig Ziglar sales tapes, and the surreal poverty of the operation including coworker Dan and his mother's complaint letter.
5moments
- 13:31Life coaches exist whose own lives are in complete shambles—getting evicted from apartments while charging people for advice.
- 14:01Tim argues motivational speakers are just skilled manipulators convincing people to do anything, not experts speaking from personal success.
- 14:38Tony Robbins succeeds by making people feel intensely in the moment—yelling in their face, forcing them to confront deep secrets in front of crowds.
- 15:16Tim was in sales in 2009 and his boss forced the team to listen to Brian Tracy tapes constantly.
- 15:37By 2009, nobody was making money or closing deals—the mortgage industry had collapsed and subprime banks were evaporating.
Tony RobbinsBrian TracyAmerican Home MortgagePat Robertson
- 4 min
Accredited Home Lenders Collapses the Day After Cramer's Endorsement
#Tim recounts how Jim Cramer praised Accredited Lending on TV only for it to collapse into hedge fund Loan Star's hands the very next day, ending his sales job and prompting his boss's ironic "good luck" quote of the day.
8moments
- 16:35Tim was on drugs while working as a mortgage salesman but says he was still good at it.
- 16:48His boss hated the sales team—fat guys and a "wany Jew" named Dan—and tried to transform them into alpha males.
- 17:07Dan's mother wrote a letter to the boss because Dan was late one day, when Dan was 26 years old.
- 17:35The boss forced them to listen to motivational tapes from Brian Tracy about sales techniques and overcoming objections.
- 18:30Brian Tracy's pitch: when someone objects on price, ask "compared to what?" to find their frame of reference.
- 19:01The second objection is deeply personal—a fear the client hasn't revealed—and you address it by saying "sir, may I ask what your hesitancy is?"
- 19:21They were sitting in a leaky office with a garbage can catching drips while the company was on the precipice of total disaster.
- 19:32The company got swallowed up in two months, and Tim moved on but remembers the motivational techniques actually worked.
- 4 min
The Drunk Bank Owner Who Slept at His Desk
#Tim describes his next job at a tiny bank run by a perpetually drunk CFO-owner who slept at his desk, made a coworker drive him home nightly, and mumbled about the mortgage collapse while half-conscious.
8moments
- 19:45Tim explains that self-improvement requires a certain type of person who realizes they're not good at something and seeks help on their own, not from a boss.
- 20:15Working in real estate, he encountered both talented salesmen and lucky mediocre ones who somehow survived in the business.
- 20:43In 2009, there was literally no one to hire for sales jobs; nobody thought real estate was a good career path while it was imploding in the news.
- 21:02Tim contrasts what happened to big bank executives after the collapse: they didn't trickle down to strip malls in Melville; they waited it out, day-traded, and eventually got rehired or consulted for side projects.
- 21:55By 2009, Tim's five-man operation had lost everyone—people quit, got fired, or were disillusioned—and the owner kept forcing them to listen to motivational sales tapes.
- 22:18The manager's tape instructed salesmen: if a borrower won't let you in their home, ask if there's a better time, and if they still say no, tell them you're a desperate guy in a strip mall with nothing to lose.
- 22:55Tim and his coworkers would actually call people using this script from Capstar, working for a collapsing subprime bank.
- 23:06The subprime bank they worked for was falling apart as Jim Cramer warned the public about it on television.
Bear StearnsLehman BrothersJim CramerGoldman SachsAccredited
- 8 min
Post-Crash Purgatory and the Obama Help Plan That Didn't Help
#Tim wraps up the mortgage-crash saga describing the impossibility of closing any deals as home values collapsed, the daily forced motivational meetings despite total hopelessness, and reflects on the drunk CFO boss's competence versus his sales failures.
13moments
- 23:23A hedge fund called Loan Star acquired Accredited and shut down all U.S. operations the very next day, after Cramer had just praised the company on air.
- 24:03The regional manager's final quote of the day before everyone got laid off was simply: 'Good luck.'
- 24:47Tim and his colleagues moved to a new small bank whose owner was a chronic drunk who slept at his desk during work hours.
- 25:16The drunk bank owner would answer the phone with instructions: 'If my wife calls, tell her I'm not here—don't tell her I was asleep.'
- 26:08When Tim asked the bank owner Bob to help close a loan, Bob called the buyer's mother in real estate, heard 'no,' and immediately returned to say the deal was dead.
- 27:00Someone at the company had to drive the drunk bank owner home every night, and during one drive he muttered apocalyptically about loans being frozen and trouble coming.
- 28:25Tim and his team were actually trying to do the right thing by getting people out of bad adjustable-rate mortgages into fixed rates, but couldn't because houses had lost 25 to 30 percent of their value.
- 28:51The Obama help plan didn't really help anybody, according to Tim.
- 29:08Management forced the entire staff to sit in a room for an hour every morning listening to motivational talks about starting the day with positive thoughts, while the company was completely dysfunctional.
- 30:05The drunk bank owner was a former CFO of a major mortgage lender on Long Island who had made serious money but was terrible at sales—he'd hang up on prospects calling them idiots.
- 30:39Despite the bank collapse, the former CFO didn't go under because he had 'white privilege,' and he likely ended up as a CFO at another company.
- 30:52The bank owner's doomsday muttering about regulators 'coming for them' turned out to be accurate—he could read the company's balance sheet and knew the collapse was coming.
- 31:08People have been contacting Tim on Twitter about topics discussed on the show.
private equityAccreditedJim CramerLoan StarObama help planHoulihans
- 3 min
Tim and Ray answer a listener question about a man owed money by his estranged sister, joking about baseball bats, banks and toxic assets, and escalating to a bit about picking up her kids for ice cream to send a message.
10moments
- 31:11Tim explains the show's mission: helping people succeed financially and socially, not morally or spiritually.
- 31:52Bilal asks for advice on collecting money his sister owes him after she stopped talking to him.
- 32:06Ray suggests bashing her car windows with an aluminum bat to scare her into paying.
- 32:25Tim's rule: never loan money to family, because you're in a position of power like predatory banks.
- 32:50Tim compares lending to his sister to subprime mortgages, calling her a toxic asset to write off.
- 33:08Ray proposes taking a shit on her lawn as another intimidation tactic.
- 33:19Ray jokes about going after her husband or kid to prove he can hurt her, referencing the show Bloodline.
- 33:40Ray suggests picking the kid up from school before the bus arrives and taking them for ice cream as a threat.
- 34:00Tim points out the contradiction: Ray won't bash her car to avoid jail time but will grab her kid.
- 34:12Tim's final advice: write off the debt and accept it was a bad move lending family money in the first place.
- 1 min
Never Lend Money to Family, Only Give It
#Tim gives his philosophy on family loan requests: stonewall people who ask for loans, and if you help anyone, give money outright rather than lending it.
4moments
- 34:25Tim's advice on refusing loans from family: just don't respond to their calls, texts, or emails.
- 34:40Email Goldman Sachs and see how quickly they get back to you when you need money — nobody helps Tim.
- 35:08Reader Pamela asks how to fit romance and sex into her life without distracting from her goals of revenge and money.
- 35:22Tim's solution: date someone who's already part of your revenge and money goals — specifically, start fucking someone with money.
Goldman SachsPamela
- 3 min
Responding to a tweet from Pamela about balancing romance with her goals of revenge and money, Tim advises dating only people wealthier than yourself and argues sleeping your way up is a legitimate strategy.
8moments
- 35:43Merge romance, revenge, and money into one goal rather than treating them as separate pursuits.
- 35:59Tim's rule: relationships should be with people who are financially secure and have significantly more money than you.
- 36:21If you can use sex to advance yourself financially, do it—it's a weapon like any other.
- 36:56The path to fulfillment is dating or fucking someone with money, which requires identifying and eliminating your red flags.
- 37:22Transcending your social class through hard work is rare, but possible.
- 37:43Most people confuse having a lot of money with being rich; having money means wanting a water slide, which disqualifies you.
- 37:57Being rich is about wanting money for purpose and power, not just accumulation.
- 38:26Staying rich requires a specific lifestyle and continuous effort, not a single windfall followed by a return to potato chips.
- 5 min
What Actually Makes Someone Rich, and the Mystery of Socialites
#Tim distinguishes "having money" from "being rich," describes the total lifestyle commitment required, compares it to Olympic athletes' monastic focus, tells the Lloyd Blankfein South Bronx origin story, and discusses socialite Jayne Wrightsman's cultivated mysteriousness.
9moments
- 39:11Tim defines wealth as a million dollars or more in liquid assets and holdings, excluding real estate.
- 39:50To make serious money, you have to want it badly and surround yourself with wealthy people.
- 40:10Tim notes that some of his happiest friends are people who don't prioritize money at all—gym teachers, comedians who do work they believe in.
- 40:31The major problem with people trying to get rich is they're unwilling to give up their social circle and comfort—the girlfriends who complain, the bar friends.
- 41:11Olympic athletes and musicians are celebrated for monastic devotion to their craft, but singular focus on making money gets you labeled a monster.
- 42:00Lloyd Blankfein, CEO of Goldman Sachs, grew up in the South Bronx projects—his name sounds regal but his origin is humble.
- 42:26If a woman wants to date a rich man and can't hold a conversation beyond movies or constantly reveals everything about herself, she fails to maintain mystery.
- 42:44Great socialites like Jane Reitzman maintain mystery not from nature but from embarrassment about their origins—she married an oilman, became friends with Jacqueline Kennedy, and never needed to constantly discuss her tough upbringing.
- 43:05Jane Reitzman of 820 Fifth Avenue—where apartments average 34 million—understood that her past didn't help her trajectory.
- 6 min
Answering a tweet asking where to vanish and start over with only $3,000, Tim advises picking cities with low cost of living and low unemployment like Houston or Vegas, and riffs on cutting off friends and family entirely to reinvent yourself.
10moments
- 43:57Someone named Crying Costas asks how to drop everyone and disappear overnight with $3000.
- 44:24Tim explains how to actually cut people off: stop talking to them, and they'll get the message within months.
- 45:24Best places to disappear — small cities have too much nosiness, big cities are anonymity but expensive.
- 46:32Tim advocates for reinvention and moving, saying he'd leave New York instantly if he weren't doing comedy.
- 46:51He's pro-grifter and pro-disappearing-to-town-with-three-grand — suggests researching cost of living and employment rates.
- 47:12Specific city recommendations: Vegas off the Strip, Charleston, Houston with its 2-3% unemployment rate and strong economy.
- 48:01Tim suspects Crying Costas may have stolen the three grand from a work credit line to fund the escape.
- 48:24Even if it's a fake Twitter account, the question is legitimate — people should disappear, ditch friends, get themselves together.
- 48:39His final advice: leave everyone, go away, get yourself together, then reach back out when successful or don't.
- 48:57Listener thanks Tim for his podcast and calls him a great philosopher despite his modest demeanor.
Houston, TexasLev PoliakovLas VegasPhoenixCrystal CostasCharleston, South CarolinaMinneapolisCleveland+2 more
- 3 min
Responding to a question about whether Freeport is a sanctuary city, Tim instead describes Freeport's nautical mile bar scene, the Helm's cheeseburger, and riffs on how corner bars and pub culture are dying in America and the UK.
6moments
- 49:30Tim spent years drinking on the Nautical Mile in Freeport, Long Island, a town of old fishermen, clam diggers, bars, and fish markets.
- 49:46The Helm bar had the best cheeseburger he's ever had, cooked on a dirty grill for 30 years.
- 49:57Tim calls certain bars "blood boxes" — places with fights and colorful characters — like Lisa's Lounge in Baldwin.
- 50:48Freeport is not a sanctuary city but a coke-dusted, drug-drenched hellhole.
- 51:36Lisa's Lounge was named after the bar owner's daughter Lisa, whose picture hung on top of the bar.
- 52:02Tim used to hang out at Lisa's Lounge with people named Bobby Haha, Chuck the electrician, Sally, and Frankie Produce.
FreeportLisa's LoungeThe Helmbar cultureblood box
- 5 min
Lisa's Lounge: Illegal Kitchens, Shit Herself Marge, and the Easter Basket Line
#Tim tells a long string of stories about the regulars at Lisa's Lounge, a Long Island dive bar named after the owner's daughter who died in a drunk driving accident, including having his illegal kitchen physically removed by bar friends, old lady Marge soiling herself, bartender Tracy's Easter basket joke, and tragic regulars.
10moments
- 52:44Tim gets reported by a rat on his block for running an illegal kitchen downstairs.
- 52:56Union guys and neighborhood characters from Lisa's Lounge help him move his stove to avoid the fine.
- 53:47Easter at Lisa's Lounge: Tim would hang out, play Tom Petty on loop, and drink with regulars.
- 54:15Marge, a regular who bought rounds for everyone, shit herself in the bar one night.
- 54:58Bartender Tracy forgot to buy Easter baskets for her kids, jokes that's why they live with their father.
- 55:19Settlement winner blew $120,000 on a woman named Carol and ended up living in a car.
- 55:38One regular's grandson shot himself; another guy from AA came to the bar every night because his friends kept him somewhat sober.
- 56:14Giants won Super Bowl in 2007 or 2008 and the whole bar erupted, especially the man whose grandson had died.
- 56:34Tim knew another guy whose friend killed himself earlier that year, but was the happiest person alive when the Giants won.
- 56:57Lisa's Lounge was a crazy, dark bar that meant everything to its people.
- 4 min
Giants Super Bowl Win and the Bar's Darkest Characters
#Tim recalls the euphoric reaction at the bar when the Giants won the Super Bowl, contrasted with the dark backstories of regulars including a grieving grandfather and a wife who drugged her husband's beer nightly to get him home.
8moments
- 57:01Tim describes the bar as a dark place he wouldn't trade for anything in the world.
- 57:20A typical Friday night involved leaving work at five, smoking a joint in the car, grabbing drinks at Lisa's, then going to the helm in Freeport and getting hammered.
- 57:53One of the bartenders named Jack lived on a boat.
- 58:09Tim went to the bar almost every night after work, trying to be home by one or one-thirty.
- 58:44Tim's friends enabled his behavior by suggesting he'd write the great American novel about the place instead of telling him he needed help.
- 59:23Tim notes that not everything is always on his sleeve and his friends couldn't tell him what to do, so they just accepted his presence there without understanding why.
- 59:49Sally's husband Bobby, the glass guy, would never leave the bar, so she'd spit a pill into his beer every night to knock him out and drag him to the car.
- 1:00:17When Bobby almost choked to death one day and recovered, Sally looked more disappointed than he'd ever seen anyone look—like she'd missed an opportunity.
- 2 min
Closing Riff: Sobriety, Dad's Enabling, and Sign-Off
#Tim reflects on being five years sober and how hard it is to describe that bar life now, shares his dad's line that every Dillon has had a dive bar in his life, then closes with plugs for Twitter questions and the GaS Digital subscription.
4moments
- 1:00:45Tim has been sober for five years and finds it strange to talk about his old bar life.
- 1:01:02His dad, an enabler, pointed out that every Dylan in their family had a real bar, citing Uncle Tommy's Buckley's.
- 1:01:15Tim imagines a rich person making that same claim and mocks how different it would sound.
- 1:01:40Tim pitches future episodes analyzing how rich people cut everyone off and isolate to succeed, then maybe help others later.