#2383 - Ian Edwards

with Ian Edwards

Published September 24, 2025
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About This Episode

Joe Rogan and Ian Edwards reflect on three decades in stand-up comedy, from New York and Boston club days to the current Austin and Kill Tony scene, breaking down how comics develop, sustain, or lose their edge. They also dive into boxing and MMA, brain damage and fighter longevity, historical boxing greats like Muhammad Ali, and broader issues of war, government deception, corporate greed, social media control, and how individuals can maintain independence and purpose in a corrupt system.

Topics Covered

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Quick Takeaways

  • Decades in stand-up reveal that massive stage time, honest peer feedback, and continued risk-taking are essential to reach a true flow state on stage.
  • Many comics with talent never make it due to bitterness, lack of persistence, or life distractions, while others reinvent themselves through new platforms like Kill Tony and social media.
  • Combat sports careers often end in physical and cognitive decline, highlighting the importance of financial planning, defensive styles, and knowing when to quit.
  • Historical and modern wars are often tied to resources and profit, with intelligence agencies and political actors manipulating public narratives for strategic and financial gain.
  • Owning your work, from social media accounts to intellectual property, is increasingly crucial as labels, networks, and platforms try to capture artists' leverage.
  • Major institutions-from news media to pharmaceutical companies-regularly mislead the public, making skepticism and independent thinking a survival skill.
  • Bad relationships, addictions, and depression can quietly derail otherwise talented people from their creative or professional paths.
  • Living slightly outside cultural epicenters can offer the balance and mental space needed to think clearly and do better work.

Podcast Notes

Opening, studio talk, and long friendship

New studio design and fake brick walls

Joe explains the old studio used thin slices of real brick on mesh, which bothered him because it wasn't a true brick wall[0:41]
He contrasts it with places that use outright plastic brick walls, which he finds especially disappointing and inauthentic
They joke about comedy venues using printed brick sheets as backdrops and how odd it is that brick walls became the standard comedy-club look[1:51]
Joe speculates it might have started with the TV show "Evening at the Improv" having a brick wall, and everyone copied it

Length of friendship and early Boston days

Ian and Joe realize they've known each other around 30 years and started together as "babies" at the Boston Comedy Club[3:01]
They marvel that when they started, they had no idea how the business worked or where their careers would end up

Ian's beginnings: Long Island, Jamaica, and TV as a roadmap

Realization that TV exposure matters

Ian talks about starting out on Long Island, seeing comics there who were funny but never appeared on TV[4:07]
He noticed that the comics who were on television were based in Manhattan, so he decided he had to get to Manhattan to progress
Joe relates from Boston: local comics could kill but without TV credits they couldn't draw paying crowds nationwide[4:22]
They note that being on TV allowed comics to tour anywhere-Kansas, Miami, etc.-because audiences had a reference point

Moving from Jamaica and early American TV

Ian came to America from Jamaica at 17; in Jamaica he grew up with only one TV channel and didn't know any American TV personalities[5:27]
Once in the U.S., he watched "Saturday Night Live" because Eddie Murphy was on it and that was a requirement culturally
Joe jokingly uses Eddie Murphy's SNL years to try to deduce Ian's age, as Ian avoids saying how old he is[5:56]

Modern SNL and movie stardom pipeline

Will SNL launch another movie star?

Joe says Cam Patterson might be the first SNL cast member in a long time with a real shot at becoming a movie star[6:47]
He contrasts this with earlier eras when Mike Myers, Phil Hartman, Adam Sandler, David Spade and others routinely transitioned from SNL to movie careers
Joe argues that SNL "did it to themselves" with overly woke content that hurt comedy movies and narrowed who they hire[7:11]

Ian's first impressions of Cam Patterson

Ian recalls bringing Cam up on stage at the Vulcan in Austin and immediately seeing how talented he was[7:44]
He even held back a helpful tag because he "didn't want to make him better" than himself, joking about simultaneous love and jealousy
Later Ian discovers that his own manager is also managing Cam, confirming his sense that Cam would be advanced quickly[8:50]

Kill Tony, Austin scene, and work ethic

One-minute sets and hard work

Joe praises Cam and others who regularly do a new one-minute set on Kill Tony, emphasizing how hard it is to generate strong new material weekly[12:00]
He lists Ari, Matty, Hans Kim, William Montgomery and others as examples of comics who grind out those minutes and work constantly
They note William Montgomery is such a wild character that he can get a minute of comedy out of almost any mundane situation[12:18]

Innate comedic presence vs pure writing

Comics whose personality is the joke

Ian describes performers like Cat Williams as having a natural "comedy cheat"-they're funny as soon as they talk because their voice and presence are inherently comedic[13:02]
He admits envy toward comics with that built-in charisma, because if they also add solid writing it's very hard to compete with them
Joe calls Joey Diaz the ultimate embodiment of this, saying Joey is funny the moment he grabs the mic purely from his look, voice and fearlessness[13:09]
They mention Theo Von and Brody Stevens as comics whose offbeat, stream-of-consciousness personas make almost anything they say funny[14:01]
Brody's repetitive catchphrases like "818 till I die" and celebrating mediocre places like Reseda became infectious among comics and crowds

The precarious middle of a comedy career

Early stage between open mics and steady work

Joe recalls when he and Ian had just moved beyond open mics and were starting to get real stage time, with no idea who would make it[15:00]
He notes several comics from that era were very good but eventually vanished, quitting to take regular jobs and later becoming bitter

Bitterness and aging out of the scene

Ian recounts a story of a veteran comic at the Comedy Store in La Jolla who reacted badly when Ian was booked as headliner and he was set to feature[16:09]
The older comic put his stuff in the headliner bedroom and then insisted he was the headliner when he arrived at the club, forcing the club to adjust payouts while Ian graciously agreed to feature
Joe and Ian see this as an example of bitterness and inability to accept a changing place in the hierarchy, something Ian is determined to avoid by staying sharp[17:33]
They note some older comics come from an era that didn't prioritize writing new material and often had other problems like heavy drug use, which can erode skills[17:54]

New York vs road work and the value of the hang

City spots, colleges, and missing the hang

Ian says once he got into New York City clubs he mostly wanted to stay there, doing sets at places like Caroline's, Stand Up New York, the Cellar, and Boston Comedy Club[21:49]
He would sometimes resent taking higher-paying college gigs because it meant missing the nightly hang with other comics in the city
Joe agrees the camaraderie and late-night parking-lot laughs were the best part of the scene and that going on the road alone feels isolating[23:04]
They describe the harshness of road work in unknown towns where middle acts would steal premises and step on headliners' material to try to outshine them[23:45]

Getting into the Cellar and New York bluntness

Ian explains he first got on at the Comedy Cellar when a comic who barked for the Boston Comedy Club noticed a no-show and asked if he wanted to go up[24:08]
SD, the booker, saw him and started giving him regular spots after that initial set
He remembers New York comics' brutal honesty-friends telling Patrice when some of his post-special material felt hacky and calling Ian out for having too many black-vs-white jokes[24:57]
On a van ride back from an out-of-town gig, fellow black comics listed all his black/white contrast jokes until he realized how many he had and adjusted

Developing material: from five minutes to universality

Expanding sets and regional limitations

They dissect the progression from getting a tight five minutes, then stretching to ten and fifteen, often diluting the initial strong chunk in the process[26:10]
Joe describes bringing someone on the road who kept repeating "one thing I love about being Mexican" because he was used to short sets and didn't know how to structure a longer one
Ian tells a story about bombing in front of about 2,000 people at Temple University because his opener, middle, and closer were all Jamaican jokes that didn't translate outside New York/DC/Florida[27:10]
The crowd booed, and he spent the night in the hotel watching "Dumb and Dumber" after deciding not to go to the after-party with comics who had all killed
He learned from that night that he needed universal truths in his act, not just regionally specific material[29:15]

International comedy, festivals, and retiring hours

Touring Europe and audience differences

Joe recalls taking Tony Hinchcliffe to Stockholm, where Tony felt like he was bombing because the big crowd's laughter pattern was different and English wasn't their first language[32:32]
Joe points out that European audiences may take a moment to process jokes in English, and that the venue size and crowd expectations also affect rhythm

Festival circuits in Australia and the UK

They discuss James McCann, an Australian comic Shane Gillis discovered and encouraged to move to America; McCann had considered quitting due to limited opportunities[32:11]
Joe explains many comics in the UK and Australia build festival hours each year around themes (trauma, politics, identity) and then retire those hours without recording them
Ian says he has asked festival comics whether they recorded those hours so they could later post them online, but many had not, missing a chance to build an audience[32:52]
They note that Edinburgh-style one-person shows often have long storytelling gaps between punchlines, which works there but would likely get steamrolled in American club environments[32:56]

Risk-taking on stage and offensive jokes

Using comedy for fun vs didactic storytelling

Joe contrasts stand-up that is about fun, silly, sometimes outrageous statements with shows that are journeys through trauma, identity, or personal evolution[34:21]
He likes saying things he doesn't believe just because they are hilariously wrong and signal that the show is play, not a sermon

Ian's self-perceived limitations and LA influence

Ian admits he holds back on saying truly wild things on stage even though he talks that way with friends, wondering if he needs to step onto that "plank" to reach his full potential[35:04]
Joe tells him he can get there and suggests it's about intention plus massive stage time-numbers matter for developing timing and fearlessness

Phones, yonder bags, and experimentation

Joe explains why his club locks up phones: it lets comics experiment with edgy premises without worrying about out-of-context clips leading to public outrage[35:28]
He notes that when trying new bits, the first wording often comes out clunky and can tighten the crowd, so he needs room to feel that, adjust, and find softer or smarter phrasing
They quote Patrice O'Neal's idea that both bad offensive jokes and great jokes come from the same place: trying to make people laugh, not to harm them[36:30]

Pursuing the flow state and "passenger ride"

Ian describes one early set where everything hit from start to finish and he felt like he was watching himself from outside his body[40:41]
That out-of-body, high-on-stage experience made him addicted to stand-up in a way he likens to drugs he hadn't even tried yet
Joe calls this the "passenger ride"-when a calmer part of you takes over, and you feel like you're sitting back watching yourself work, instead of overthinking like a backseat driver[40:31]
He compares the internal critic to a nervous passenger shouting driving instructions, and says real mastery is learning to quiet that voice

Recording sets and creating an informal curriculum

Importance of taping and reviewing sets

Joe credits Boston comic Mike Donovan for instilling the habit of recording every set, because off-the-cuff tags can become the best punchlines and are easily forgotten[42:57]
Ian now records his sets and finds lines during playback that he doesn't remember saying but that become among his best
They acknowledge it's unpleasant to listen to your own voice after a show, but see it as necessary extra work to refine bits[44:18]

Mothership structure as a training ground

Joe outlines how his Austin club offers open mic nights, door-person spots for real comics, and exposure to top acts like Colin Quinn, Shane Gillis, Jimmy Carr, and Ian himself[47:01]
He frames it as an unprecedented education in stand-up: comics can watch greats, ask questions, and see how the art form is really practiced
He calls Kill Tony the number one breakout platform for new comics in America, where one killer minute can change someone's entire life trajectory[47:26]
They imagine a comic scraping together money, driving to Austin, failing to get up for weeks, then finally crushing their minute and going from anonymous to professional touring comic
Joe notes some people have literally done stand-up for the first time in their life at a sold-out Kill Tony in a massive venue, which he likens to fighting a prime Mike Tyson in your first boxing match[49:23]

Combat sports, brain damage, and emotional toll

Watching friends fight and fear of damage

Joe describes how emotionally hard it is to watch friends like Daniel Cormier or Brendan Schaub get beaten up or knocked out, knowing the long-term physical costs[51:06]
He explains Schaub had taken many concussions in sparring with heavy punchers like Shane Carwin, sometimes days before big fights, which shaped Joe's strong advice that he retire

Boxers and lifelong damage

They discuss Peter McNeely, who rushed Mike Tyson in Tyson's comeback fight, and Joe questions what one knockout like that does to the rest of your life[53:30]
Joe references Jerry Quarry, an Irish heavyweight known for wars with big punchers, who later suffered severe CTE and dementia, as did his brother with far fewer pro fights[54:00]
Ian notes that besides documented ring wars, fighters like Quarry may have had countless unrecorded bar fights that added to the overall damage

Muhammad Ali: prime vs post-layoff

Joe contrasts Ali's performance vs Jerry Quarry after his three-year forced layoff with his earlier, nearly untouchable version against Cleveland "Big Cat" Williams[56:01]
He highlights Ali's footwork and head movement in the Williams fight as something never seen before in the heavyweight division, like a middleweight among heavyweights
They discuss how Ali lost three prime years (ages roughly mid-20s to late-20s) due to refusal to serve in Vietnam, and speculate that Frazier and Foreman might not have beaten the pre-layoff Ali[56:01]
Joe acknowledges that the forced break might have postponed brain damage but also meant Ali had to rely more on his chin later, taking more clean shots

Ali's charisma and political impact

Ian says Ali was so entertaining he can just watch compilations of Ali talking, not even fighting, because he was stand-up-comedy-level funny[59:18]
Joe recalls Ali boasting he'll turn off the light and be in bed before the room gets dark, and notes no one before him had combined that movement and trash talk
They emphasize Ali's symbolic role as a voice for the anti-war and civil rights generation, initially vilified as a traitor but later recognized as being on the right side of history[1:00:26]

War, drugs, and distrust of government narratives

Vietnam, Afghanistan, and opium

Joe says he believes the Vietnam War was partly about controlling the opium trade and draws a parallel to Afghanistan, where heroin production increased after U.S. involvement[1:02:41]
He mentions footage of U.S. troops guarding poppy fields and a TV segment where a soldier rationalizes it as protecting farmers from enemies, which Joe sees as gaslighting
Ian brings up Rambo III thanking anti-Soviet fighters in Afghanistan in its credits, pointing out that at one time the U.S. funded groups later labeled as enemies[1:03:50]

Proxy wars and Ukraine

They frame the Ukraine conflict as another proxy war, where NATO and the U.S. fund one side while Russia reacts to perceived encroachment, and Joe sees both sides' arguments[1:05:44]
Joe notes Ukraine's enormous rare earth mineral and natural gas resources and mentions concerns about U.S.-connected energy ventures there

Freeway Ricky Ross and Iran-Contra

Joe references interviews with Freeway Ricky Ross, who moved huge amounts of cocaine in Los Angeles without realizing he was indirectly working for the U.S. government funding foreign conflicts[1:09:05]
They mention the Iran-Contra era as one where war games, covert funding, and drug trafficking were intertwined without public oversight

Nixon, JFK, Watergate, and institutional deceit

Nixon, drug laws, and psychedelics

Joe argues Nixon's sweeping criminalization of psychedelics was aimed at anti-war and civil rights movements, changing the direction of culture by jailing activists[1:11:33]
He wonders how society might look today if psychedelics had remained legal from 1970 onward

Bob Woodward, Belushi book, and Watergate skepticism

Joe recounts Bill Murray saying that after reading a few pages of Bob Woodward's book on John Belushi and seeing distortions, he thought, "Oh my God, they framed Nixon"[1:13:30]
This made Murray retroactively question Woodward's reporting on Nixon, seeing how a narrative could be shaped around someone he knew personally
Joe questions whether Watergate, while illegal, warranted its historical weight compared to the constant large-scale surveillance and hacking that likely occurs today[1:13:01]

Smedley Butler and "War is a Racket"

They discuss Major General Smedley Butler, who wrote "War is a Racket" in 1933 and later testified about a business plot to use him in a coup against FDR[1:15:06]
Joe notes that congressional findings acknowledged such a plot was discussed and planned, but no one was prosecuted, reinforcing his view that elites have been "dirty" from the beginning

Money, corporations, and wealth transfers

2008 crash, COVID, and who benefits

Ian asks where the money went in the 2008 financial crisis, pointing out that lost wealth didn't vanish-it must have gone to someone[1:18:07]
Joe describes COVID as the biggest transfer of wealth in modern history, with small businesses shuttered while large chains and platforms captured their customers[1:18:47]
He notes that restaurants in places like Los Angeles were closed en masse while big box stores and fast-food chains stayed open, and that large corporations received significant stimulus money

Corporate logic and sociopathy

Joe says corporations, by design, always want more money and will often choose profits over people, justifying harm through legal teams and PR[1:21:29]
Ian wonders why companies spend so much money lying and fighting lawsuits instead of investing that money in making healthier, safer products from the start
Joe differentiates between builders like Elon Musk, who make tangible products, and financial actors whose sole goal is multiplying numbers, often at others' expense[1:22:33]

Record labels, streaming, and ownership

Modern music deals and artificial virality

They discuss how streaming platforms changed artist revenue streams and how labels can manufacture "viral" hits by juicing promotion and algorithms[1:27:12]
Ian questions whether anything is organically viral anymore or mostly artificially boosted by corporate interests
They highlight that labels now often take a cut of touring, which used to be where artists made real money to compensate for bad record deals[1:27:55]

Social media control and contract traps

Joe recounts that some TV networks tried to require artists to hand over control of their social media accounts as part of show deals, including the right to post on their behalf and plug other shows[1:29:56]
He refused such a deal, insisting that anything posted under his name must come from him, and notes several friends had already signed away that control
They mention a case where a host of a talk show lost access to social media accounts built over years when the show ended, showing how contracts can strip artists of their own audiences[1:30:36]

Aliens, surveillance, and changing public skepticism

From ostracizing UFO talk to mainstream doubt

Ian says he believes in aliens partly because of the intensity of official denials, noting that in the past people who believed in UFOs were socially ostracized[1:36:26]
They compare this to shifts in trust toward law enforcement and government; things many black Americans distrusted for decades are now widely questioned by others too[1:36:41]

Mass surveillance and intelligence agencies

Joe references Edward Snowden's revelations about large-scale NSA surveillance, saying what Nixon did with Watergate is now done digitally to everyone with smartphones[1:39:07]
He jokes that anyone who knows him likely has a "bugged" phone, and that all their explicit photos and data exist somewhere in "the ether"
They note that intelligence work likely involves newer, little-known agencies beyond the CIA and NSA, and that black-budget operations make oversight difficult[1:40:18]

Growing up, school, and choosing comedy over convention

School as factory training and immigrant pressure

Ian observes that school routines-bells, moving class to class-train people to be worker drones, reinforcing a factory model of life[1:42:15]
He shares that as an immigrant kid he felt pressure from his family to work hard and make their sacrifices worthwhile, so he followed the academic blueprint through high school and into college[1:42:51]
College is where things started to feel "wonky" for him, as the prospect of a conventional career clashed with his interest in comedy

The switch that couldn't turn off

Ian describes the moment he decided to do comedy as flipping a switch that then broke in the "on" position; after that, there was no real risk calculation-this was simply his life path[1:45:06]
Joe notes that some people reach similar decision points but can't beat their demons-depression, addiction, or toxic relationships-and drift away from their creative calling[1:44:52]
He emphasizes that many talented people get stuck in bad relationship dynamics that function as massive distractions from their goals

Lifestyle choices: LA vs outskirts, New York geography, and downtime

Living outside the Hollywood chaos

Joe explains he intentionally chose to live 30 miles outside Los Angeles rather than in Hollywood because he needs quiet, nature, and downtime to think clearly[1:48:12]
He describes wanting to wake up, drink coffee on the porch, hear birds, and watch deer instead of being surrounded by constant urban noise
Ian, by contrast, lived in Hollywood "in the cut" near the hills, liking the proximity to the scene while still having a relatively quiet spot off the flats[1:49:16]

Borough pride and Long Island chip-on-shoulder

They talk about how Long Island, not being one of the five NYC boroughs, always had to "go hard" to get respect compared to places like Brooklyn or the Bronx[1:51:24]
Joe compares this to people from outside Boston claiming they're from Boston for credibility, while locals will press them on what specific neighborhood they're really from

Fighting careers, age limits, and financial planning

Journeymen fighters vs champions

Joe says fighters either chase being world champions or accept becoming journeymen who fight for paychecks, a brutal way to live with no long-term guarantee[1:54:11]
He notes that some fighters make real money without belts-citing examples like popular veterans-and emphasizes the importance of saving, as one champion publicly mentioned having millions saved[1:54:06]

Bernard Hopkins' defensive philosophy

Ian admires Bernard Hopkins for prioritizing self-preservation in the ring, tying up opponents and limiting clean shots as a deliberate strategy to avoid CTE[1:55:35]
They recount how Hopkins fought effectively into his late 40s but also note the disturbing image of his final fight where he was knocked out of the ring and landed on his head at age 50

Comedy mindset: turning pain into material

Every bad event as potential material

Ian says he never sees a bad date as a total loss; if it goes well, it's enjoyable, and if it goes badly, it's good material for the stage[1:57:54]
He admits that even during heartbreak, a part of him is thinking ahead to how he'll eventually talk about it on stage once the emotional cloud lifts[1:58:54]
He even views car accidents or other mishaps as potential stories, highlighting how deeply the comic lens is embedded in his thinking

Lessons Learned

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

1

Long-term excellence in any craft demands massive, consistent reps and honest feedback, not just early talent or occasional inspiration.

Reflection Questions:

  • Where in your current work or hobbies are you relying on talent instead of deliberately accumulating high-quality repetitions?
  • How could you create a structure-like regular reviews or feedback from peers-that forces you to confront what is and isn't working?
  • What is one skill you say you care about that you could commit to practicing on a fixed schedule for the next 90 days?
2

Bitterness and comparison are corrosive; focusing on your own growth and adapting to changing conditions is the only sustainable path.

Reflection Questions:

  • In what situations do you find yourself resenting others' success instead of analyzing what you can learn from them?
  • How might your behavior or choices look different if you assumed your best years are still ahead of you rather than behind you?
  • What is one area where you need to update your approach instead of clinging to an old identity or way of doing things?
3

Owning your platforms and intellectual property-whether it's your social media, email list, or creations-protects your leverage in a system that often exploits creators.

Reflection Questions:

  • Which parts of your work or audience do you currently depend on third parties for, and how vulnerable would you be if those were taken away tomorrow?
  • How could you start building a direct relationship with the people who value your work, instead of routing everything through intermediaries?
  • What contracts, terms of service, or deals have you agreed to that you should revisit with a more critical eye?
4

Mainstream narratives about war, politics, and institutions are frequently shaped by hidden incentives, so skepticism and independent research are essential.

Reflection Questions:

  • Which major historical or current events have you mostly understood through headlines rather than primary sources or long-form investigations?
  • How could you build a habit of cross-checking stories you hear with at least one source that has no obvious financial or political stake?
  • What is one belief you hold strongly about geopolitics or government that you could deliberately interrogate from the opposite perspective?
5

Bad relationships, addictions, and unmanaged mental health issues can quietly derail even the most talented people from ever realizing their potential.

Reflection Questions:

  • Where in your life do you sense a recurring pattern of chaos or drama that consistently pulls your attention away from meaningful work?
  • How might your trajectory change if you put as much structure into protecting your mental and emotional bandwidth as you do into your tasks and goals?
  • What is one concrete boundary you could set this month to reduce a known source of distraction or toxicity in your environment?
6

Finding your personal "flow state" requires both technical preparation and deliberately creating conditions-like rest, physical health, and reduced self-criticism-that let you get out of your own way.

Reflection Questions:

  • When was the last time you felt like a "passenger" in your own performance or work, and what conditions preceded that state?
  • How could you adjust your daily routine-sleep, exercise, warm-up rituals-to make that kind of flow more likely to occur?
  • What specific form does your inner backseat driver take, and what experiment could you run to quiet it during your next high-stakes situation?
7

Comfort with calculated risk and the willingness to occasionally offend or fail publicly are prerequisites for creative breakthroughs.

Reflection Questions:

  • What topics, ideas, or experiments do you avoid in your work because you fear how others might react?
  • How could you create a safer "sandbox" environment-like a small test audience or private draft-where you can explore edgier or more experimental ideas?
  • What is one small public risk you could take this week that would stretch your comfort zone without jeopardizing your integrity?
8

Deliberately choosing where and how you live can support clearer thinking and better work by giving you the right mix of stimulation and solitude.

Reflection Questions:

  • Does your current physical environment energize you, drain you, or simply distract you-and how do you know?
  • How might your creative output or decision-making improve if you had more intentional downtime away from constant noise and social pressure?
  • What is one realistic change you could make to your living or working space in the next three months to better support focus and recovery?

Episode Summary - Notes by Kai

#2383 - Ian Edwards
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