We react to Bill Ackman's advice to young men

Published November 20, 2025
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About This Episode

Two co-hosts discuss Bill Ackman's formal pickup line "May I meet you?" and share their own dating and pickup line stories before pivoting into examples of bold young entrepreneurs building "man-on-the-street" content businesses. They then dive into the origin story of MTV and its creative leadership, using it to explore the importance of planting a clear strategic flag, underestimating upside, and taking simple ideas very seriously. The conversation broadens into creative careers in animation, the power of curiosity and observational sensitivity in comedy, investing, and AI, and ends with a Jerry Seinfeld quote on proportion and knowing when to stop.

Topics Covered

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Quick Takeaways

  • Bill Ackman's hyper-formal pickup line "May I meet you?" sparks a broader discussion about what actually works in real-world flirting and the importance of delivery over specific words.
  • A 19-20-year-old college dropout built a multimillion-dollar agency by productizing TikTok-style street interview ads that most founders are too shy or exhausted to film themselves.
  • The founders and programmers behind MTV, Nickelodeon, and Comedy Central deliberately hired unconventional, pot-smoking, back-of-the-class artist types and schooled them into showrunners, yielding iconic series like SpongeBob, South Park, and Chappelle's Show.
  • Planting a clear flag-like betting on email at The Hustle or meditation at Calm-can be more powerful than constantly pivoting, even when early results are lukewarm and investors are skeptical.
  • Founders often drastically underestimate how big their businesses can become and how much a great product can expand the total addressable market over time.
  • Tim Westergren kept Pandora alive by persuading dozens of employees to work without pay for many months, continually framing their work as culture-changing and once-in-a-lifetime.
  • A small Australian animation studio used game engines and YouTube to create an original show with hundreds of millions of views, monetizing primarily through merchandise before streaming platforms came calling.
  • Great investors, entrepreneurs, and comedians share a heightened sensitivity to details others ignore, asking unusual questions-like why slavery ended-that lead to deep insight.
  • Jerry Seinfeld's decision to turn down $110 million for another season of Seinfeld is used to illustrate his belief that proportion-knowing how much is enough-is crucial to making art great rather than mediocre.

Podcast Notes

Opening banter and Bill Ackman "May I meet you" discussion

Setup of the "May I meet you" meme

One host excitedly announces he has the "best opener" and asks to "meet" Sam, leading into a discussion of the "May I meet you" phrase[0:00]
They reference seeing the "May I meet you" quote online connected to Bill Ackman and note they will do a deep dive on it as the first topic[0:20]

Bill Ackman and Magic Johnson's Twitter styles

They describe Bill Ackman as "the great Bill Ackman," a prolific billionaire activist investor who runs Pershing Square Management[1:22]
Ackman is said to buy stakes in companies he thinks are undervalued and to short companies where he believes there is wrongdoing or malfeasance, speaking out publicly about them
They mention his high-profile short campaign against Herbalife, which one host says "burned" him, as an example of his activist style
Magic Johnson is used as a comparison for "using Twitter wrong" by posting extremely obvious sports observations like "whoever scores more points" will win[0:46]

Reading and reacting to Bill Ackman's tweet about meeting women

Ackman tweets that many young men find it difficult to meet young women in public settings because online culture has eroded their ability to spontaneously meet strangers[2:21]
One host reads this part and agrees, nodding along and saying he is glad Ackman is speaking on the issue
Ackman says he wants to share words he used in his youth and then reveals his line: "I would ask, may I meet you?" before further conversation[2:39]
He claims he "almost never got a no" and that this polite, grammatically correct question opened the way for further conversation and meeting interesting people
Ackman attributes the line's effectiveness to "proper grammar and politeness" and says it can work for women seeking men and same-sex interactions
The hosts react with disbelief and humor, one repeatedly saying "Oh my God" at the formality of the line[2:58]

Hosts compare "May I meet you" to their own real-life pickup experiences

One host says when he met his wife in real life he used a crude joke comparing chickpeas and lentils and implying paying to have a lentil on his face, and it worked[3:44]
He notes he made a joke about someone peeing on his face, is relieved it worked, and contrasts that with the extreme politeness of "May I meet you"
One host jokes that if a woman responds positively to "May I meet you" she might not be someone he wants to go out with, then softens it by saying he is joking somewhat[4:35]
They both agree that straightforward, casual approaches like "what's going on, do you want to hang out sometime?" can be effective, but "May I meet you" feels off[4:19]
One host states his belief that in flirting, as long as the girl laughs you can say almost anything, so delivery and tone matter more than the exact words

The viral spread and parody of "May I meet you"

They mention Tinder putting up a "May I meet you" billboard and people making videos walking up to attractive women saying the line[4:25]
One host observes people are "going crazy" with the meme and says it made him think about whether the line might actually work and about making their own top formal pickup lines[4:53]

Hosts invent their own humorous pickup lines and discuss dating dynamics

Brainstorming alternative formal pickup lines

One host offers to write some of their own pickup lines for young men, questioning why Ackman should be the only one giving such advice[6:19]
He proposes "May I take your jacket?" as a "close cousin" to "May I meet you"[6:48]
He jokes this opener gets her undressing, involves a generous act, and is likely to elicit a "yes," starting what he calls in sales a "yes ladder"
Another host points out she might just think he works there as staff, and he would then need to bridge that gap
Second suggested line: "Are you cold?" based on the observation that women tend to be cold and might feel seen and understood by that question[7:16]
They joke about using a jacket from a previous girl to warm the next girl approached, highlighting the absurdity
Third suggested line is simply pretending to be Bill Ackman: "Hey, I'm Bill Ackman. I'm the billionaire founder of Pershing Square. Nice to meet you."[8:47]
They agree this would work but requires significant "pre-work" such as actually being tall, rich, and successful like Ackman

Bill Ackman's advantages and cultural references

One host says he is pretty sure Ackman was worth $10 million at age 27 and notes Ackman is about 6'3", making him a handsome, tall, rich man giving dating advice[8:56]
They argue Ackman may have inadvertently tapped into a desire stoked by shows like Bridgerton for formality and princess-like treatment[9:27]
Another host says that when he tried to be proper as a kid he just looked like Napoleon Dynamite, especially with braces and an afro, and that "nothing really worked" for him romantically then[9:34]

Hampton, office dynamics, and women dating uglier men

One host notes his company Hampton has around 20-25 employees, of which about 20 are women, joking that "men are getting left behind"[7:57]
He shares that he overhears his female employees bragging about having boyfriends uglier than they are, as they want to be the hot one in the relationship[8:17]
Both hosts say they had never heard this before but feel it explains a lot in hindsight

Street interview content business and "white belt" entrepreneurship

Origin story of the 203 Media street-interview agency

They describe a style of TikTok video where a young person interviews attractive strangers in parks like Washington Square about products such as deodorant or chocolate[11:19]
A young entrepreneur named Oliver from Tabs Chocolate hired another young man, Josh, then about 19, to film testimonial-style street interviews in Washington Square Park[11:40]
The videos were meant to look organic, function as testimonials for TikTok, and are said to have worked well, helping Tabs Chocolate become popular
After initial success, Josh realized he could offer this service to other brands, dropped out of Syracuse University around age 19-20, and started an agency[12:01]
They say Josh's company is now making about $300,000 a month in revenue with roughly 46 employees, many being freelancers, filming in parks in New York, Los Angeles, and Miami[12:05]
Josh tells the Wall Street Journal he relentlessly DMed founders on Twitter, offered free work to build a legit-looking portfolio, and hustled to grow the business

Why the street-interview format works and the role of boldness

One host compares Josh's work to missionary or door-to-door work, saying it's exhausting and exposes you to rejection and humiliation, which most founders want to avoid[13:19]
They highlight that Josh productized a specific ad format (street interviews) that performs well on social, doing something most founders are too embarrassed or busy to do themselves[13:51]
They note Josh sometimes walks 30,000-50,000 steps a day, about 10 miles, while filming, underscoring the physical hustle involved[13:39]
One host suggests Josh alone could likely have made around $300,000 a year personally doing this before scaling with more people[14:01]
They frame the key skill as boldness and willingness to "get after it" by approaching strangers on camera, more than any special technical expertise[14:36]

High-cost agency work and founders' fear of street outreach

They share that their friend Ramon paid Josh "tens of thousands of dollars" to produce these videos, highlighting how much people are willing to pay to avoid doing the awkward work themselves[14:33]
One host DMed and then called Josh after seeing his Twitter feed, joking that he opened with "May I meet you, sir?" and says Josh is "a real hustler" who listens to the podcast[14:40]

"White belt business" concept and call to action for young listeners

One host introduces the term "white belt business" to describe a good first business where you're at your worst as an entrepreneur and still building skills, network, and capital[15:06]
He says your first business is likely to be one of your worst but is still valuable because it gets you into the game
They argue Josh's street-interview agency is an excellent example of a white belt business, accessible to anyone willing to work hard and be bold[15:47]
One host directly challenges 18-25-year-old listeners who claim they want success badly: if they hear this and don't try something similar, he says he is "calling their bluff"
They add that this model can work in big cities or even suburbs, with a possible shtick of interviewing everyday people in places like Costco[16:06]

School of Hard Knocks short-form interview content

They mention a creator with a page called "School of Hard Knocks" who started with man-on-the-street Instagram shorts and now gets far more views than their own show[16:11]
The hosts describe his format as very short interviews where he holds a mic, asks a quick question to successful people, and compiles one-minute clips[17:08]
They note that although it feels like bumping into celebrities like Shaq or Tom Cruise, these interactions are now often pre-arranged because those figures see his content and agree to meet
One host comments on the creator's youth, noting his "broccoli haircut" and guessing he must be under 27, and praises the effectiveness of the short compilation format[17:01]

MTV, Nickelodeon, and planting a strategic creative flag

Tom Freston and the birth of MTV and related networks

They discuss a Wall Street Journal article about Tom Freston, who led programming at MTV and later oversaw Nickelodeon and Comedy Central properties[18:09]
MTV started in 1981 as a music video channel created by Warner, with a small leadership group of "punk rock/hippie" types tasked with figuring it out[18:01]
One quoted anecdote says the receptionist sold cocaine and the only office clothing rule was "no frontal nudity," illustrating the wild early culture
They list shows that came out of this ecosystem: Blue's Clues, Beavis and Butt-Head, SpongeBob, Daria, The Daily Show, Jackass, South Park, Crank Yankers, Fairly OddParents, Chappelle's Show, Avatar: The Last Airbender, Colbert Report, Ren & Stimpy, The Real World, Dora the Explorer, and Rugrats[18:59]
One host jokes he's going to have a "nostalgia seizure" hearing all these titles, underscoring their cultural impact on their generation

Freston's hiring philosophy: pot-smoking back-row artists

They quote Freston saying MTV should find "pot smoking guys" from the back of the class who could draw and had characters living in their heads, like the creator of SpongeBob[19:53]
Freston wanted to recruit people who knew nothing about making TV shows, school them, and rapidly produce series with them
The hosts see this as both silly and "brilliant," admiring the romanticism of betting on unconventional, uncredentialed talent[20:07]

Planting a flag vs. endless iteration in business

One host contrasts Freston's strong stance with a common startup pattern where founders constantly iterate toward ideas instead of making a clear bet about "what we are"[20:42]
They cite Barstool as a company that planted a flag around a specific attitude and voice, and Vice as a company that defined itself as youth culture and sent inexperienced reporters to extreme locations[20:57]
Pixar is mentioned as another example, betting that computer animation could tell stories as well as or better than live-action film[21:04]
They argue that having a clearly articulated bet, even an unusual one like giving creative control to potheads, can be more powerful than directionless iteration[21:44]

Examples of planting a flag: Calm and The Hustle

One host praises Alex Tew and Michael Acton Smith from Calm for staying committed to meditation as their core mission, despite lukewarm early results and investor disinterest[21:37]
Calm tried many different products around the same theme-like "Do Nothing for Two Minutes" and an app called Checky that counted how many times you checked your phone-before sleep stories finally drove major growth
The other host credits Sam for planting a flag with The Hustle by committing to email and independence instead of chasing Facebook video or Snapchat trends[23:46]
He recalls Sam calling The Hustle a "pirate ship" and saying every email subscriber was more wind in his sails, and even getting a pirate ship tattoo despite the company being "just a newsletter" on the surface

Underestimating upside and the Pandora story

Regrets about underestimating The Hustle's potential

Sam admits his mistakes included not sticking with the same plan through pushback and underestimating how big The Hustle could become[24:41]
He recalls The Hustle doing $12 million in revenue the year they sold and thinking it might reach $50-70 million, which he now considers a foolish underestimate[25:25]
He notes Morning Brew, a competitor that only sold part of its business, reached $90 million in revenue, and says other similar companies are doing hundreds of millions
They argue founders forget that once a product is really cool, the total addressable market can expand significantly beyond what early numbers suggest[25:48]
One summarizes a rule of thumb: everything takes longer than you expect, but can become bigger than you expect, even if you think you are already being ambitious[25:57]

Tim Westergren and Pandora's early struggles

Sam recounts hosting Tim Westergren, founder of Pandora, at an event and later writing The Hustle's first viral article about him: "Here's how Pandora's founder convinced 50 early employees to work for two years without pay"[26:54]
Pandora began as the Music Genome Project, raising $5 million and hiring 50-100 struggling musicians to tag songs with about 50 musical attributes in a spreadsheet to build a large database
They explain that the initial product iteration, using the database in Best Buy to suggest CDs similar to a sampled song, did not find product-market fit, and the money ran out[27:25]
Despite running out of money, Westergren felt the technology was "magical" and convinced employees to work for roughly 18 months without pay while they searched for the right product application[27:44]
Sam shares Westergren's speech to employees emphasizing that they had created something unique solving a gigantic problem, that everyone loves music, that millions of musicians and listeners can't find each other, and that when their product found its home it would change culture[28:15]
Westergren framed working at Pandora as a once-in-a-lifetime chance to change culture, asking how many times in life one can say they had that opportunity
One host says this kind of grand, elevated framing is almost its own skill, and compares it to how Elon Musk describes SpaceX as making humans multi-planetary to save consciousness[28:52]

Elevating seemingly mundane products: Dyson and cocktails

They discuss Dyson, noting it mainly makes vacuums, hand dryers, and blow dryers, but has become a "cool" company because its CEO frames it as the standard of excellence rather than as a simple appliance maker[30:14]
They argue that with more than about 15 employees, a leader's job is significantly about creating this kind of compelling narrative and sense of mission[30:11]
They mention Nick Gray, who took the simple idea of hosting two-hour cocktail parties, treated it as a serious art and science, wrote a book about it, and saw it open many doors[31:09]
One host concludes that many successful people have simply taken a simple idea extremely seriously, to a degree others would not expect or consider necessary[31:09]

Creative careers in animation and YouTube originals

SpongeBob creator's path and the appeal of animation

They mention Sean's book series project at onehourbooks.co and suggest he research MTV, Comedy Central, Nickelodeon, and especially the creator of SpongeBob for creativity insights[33:40]
Sam summarizes the SpongeBob creator Steve's path: first a grade school teacher in San Francisco, then a marine biologist, then at about age 28-29 he went to school for animation because he loved drawing comics[34:04]
Steve eventually worked his way into Nickelodeon, worked on Rocko's Modern Life, then pitched SpongeBob, drawing on his passion for marine biology
They recall SpongeBob feeling "silly" and slightly suspect to parents, but not inappropriate, and Sam finds it beautiful that adult passions (like marine biology) can lead to iconic children's content[34:24]
Sam laments that on modern YouTube there is not much fiction-style or animation content akin to what he loved as a kid and says he would love to see more of it[34:37]

The Amazing Digital Circus and indie animation success

They recall meeting brothers from Australia who created "The Amazing Digital Circus" and posting a pilot on YouTube that reached about 398 million views[35:07]
The brothers used a game engine like Unreal or Unity to produce an animated show with dark humor, similar to anime but tailored to Western audiences
Sean notes that MrBeast (Jimmy) invited this creator as one of the few people he wanted at an event, even saying this guy might be better than him, which impressed the hosts[36:45]
Initially, the Australian team decided they were unlikely to land Netflix or Hollywood deals, so they focused on just making something great for YouTube instead[37:07]
They report the business model was largely merchandise, with the creators making tens of millions from fan merch tied to their original IP[37:07]
Later, a major streaming platform like Amazon Prime or Netflix cut a deal for the show, and the creators negotiated to keep the content on YouTube to maintain their fandom there[37:17]
Sam reflects that when he met the creator he was just one of 20 interesting people, but in hindsight he finds the story romantic and badass, wishing he had appreciated it more in the moment[38:36]

Curiosity, observation, and unusual questions in comedy, investing, and AI

Ben Horowitz, Toussaint, and asking non-obvious questions

They mention having Ben Horowitz on their show and ranking him in the top 10 of about 750 guests in terms of wisdom[39:17]
One host describes Ben as a surprisingly well-balanced, normal-seeming "great hang" compared to some extreme, sharp-edged outliers in tech[40:10]
By contrast, they describe his partner Marc as obviously extremely intelligent, with a physically larger head like LeBron's height being a visible difference[40:45]
Ben had read about Toussaint Louverture, a slave who became leader of a 500,000-person army in Haiti and led a rare successful slave revolt that ended slavery there[41:57]
After the podcast, Ben explained he got interested because he was thinking about why slavery, which had been a core economic model for thousands of years across civilizations, ever ended[41:57]
He noted that aqueducts in Rome and pyramids were built by slaves and that slavery emerged independently in many places as the "functioning economic model" of the time
The hosts emphasize that Ben did not mean slavery was good, but that he was approaching it from first principles: if it was entrenched and economically central, it's interesting to ask what forces led to its end[42:59]
One host says he realized this revealed Ben's "special sauce": he asks questions others would never think to ask, rather than accepting things at face value[43:33]

Sensitivity and observation in comedy and parenting

Sam references an Eddie Murphy Netflix documentary where Murphy describes comedians as more sensitive than others, noticing tiny details like a scratch on a new car or a faint smell in a room before anyone else[44:46]
Murphy says comedians are artists who use comedy as their medium and are the first to comment on such details, turning them into bits[44:46]
Sam notes Murphy became famous extremely young, was on SNL at 18 and the star of a major movie in his early 20s, and remained sober while many of his peers died from drugs[45:11]
They connect Murphy's notion of sensitivity to Ben's curiosity, suggesting that insightful people fixate on specific lines or facts others skip past[45:35]
One host says having kids reveals how shallow adult knowledge can be, as children ask basic questions like how buildings are built or why boys can show nipples and girls cannot, which adults often cannot answer[46:39]
He criticizes how many things people accept without examination, and says great thinkers pick up "things on the floor"-overlooked questions-and explore them

Observation in investing and Seinfield-style comedy

They say great investors like Warren Buffett also just notice mispricings others ignore, reading dense manuals like Moody's front to back to find anomalies that spark curiosity[47:27]
Sean keeps a running document called "Seinfeld premises" to label everyday observations that could be the basis of Jerry Seinfeld-style observational jokes[48:04]
They recount Seinfeld's bit about people apologizing for dropped calls and saying "I don't know what happened," when in reality no one knows how phones work well enough to know what happened, highlighting its absurdity[48:34]
Sean shares an example from his list: airlines letting soldiers board only slightly earlier than regular passengers, which he finds an absurdly small "perk" given the sacrifices involved[49:16]
He says soldiers still go through TSA, even though they are "security," and jokes that the reward should be far more extravagant than boarding 30 seconds earlier
He also compares military medals to participation medals from children's soccer, noting the mismatch between sacrifice and token reward[50:00]

AI breakthroughs and who really noticed the shift

They note that AI and neural networks have been studied for decades, yet the leaders of current AI companies were not usually the original academic experts[50:36]
Sean highlights the Google paper "Attention Is All You Need," written by a small group of researchers, as the key breakthrough showing attention-based models could dramatically change outputs[51:22]
He points out the irony that Google, which had poured billions into machine learning, published the paper but did not act on it aggressively, leaving others to recognize its significance[51:06]
He describes DeepMind as among the first to notice the potential, leading Google to acquire it, and then Elon Musk noticing that DeepMind's progress represented the AI people had been talking about for 40 years[51:58]
Musk worried that Google had a monopoly on AI talent and that Larry Page did not prioritize AI safety, viewing AI as an inevitable next evolutionary step for humans[52:58]
To counterbalance Google's dominance, Musk helped create OpenAI to open-source AI research and spread talent and capabilities more widely[53:33]
Sean likens Google to a treasure hunter whose metal detector beeps but who keeps walking down the beach instead of stopping to dig, emphasizing how even experts can miss paradigm shifts[53:33]

Jerry Seinfeld on proportion and knowing when to stop

Seinfeld turning down $110 million and the idea of proportion

They mention a quote from Sean's "Five Tweet Tuesday" email about Jerry Seinfeld turning down $110 million for one more season of Seinfeld, the largest TV offer at the time[53:57]
When asked why he declined, Seinfeld said the most important word in art is "proportion"-how much, how many words, how many minutes[54:14]
Seinfeld argued that too much of anything, like too much cake, changes the entire feeling, and that getting proportion right is what makes work art instead of mediocre[54:21]
The hosts react by calling the quote "so good" and choose to end the substantive conversation there, treating it as a fitting closing note[54:25]

Lessons Learned

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

1

Picking a simple idea and taking it extremely seriously over a long period often matters more than picking a novel idea; many successful founders and creators win by planting a clear flag and refusing to drift, even when early responses are lukewarm.

Reflection Questions:

  • What is one deceptively simple idea in my work or life that I could commit to taking far more seriously than I have so far?
  • How might my results change if, instead of constantly pivoting, I planted a flag around a specific mission and stayed with it for the next 2-3 years?
  • What concrete decision can I make this month to signal-to myself and others-that I am fully committed to a chosen direction?
2

Boldness in doing uncomfortable, high-friction work-like approaching strangers on camera or selling door-to-door-can create opportunities others are literally paying to avoid, making it a powerful competitive edge for young or under-resourced entrepreneurs.

Reflection Questions:

  • Which tasks or outreach activities do I currently avoid because they feel embarrassing, scary, or beneath me, but could actually move my goals forward?
  • How would my trajectory change if I treated discomfort and social risk as signals that I'm working on things others will shy away from?
  • What is one specific uncomfortable action (a call, a pitch, a public experiment) I can schedule and execute within the next seven days?
3

We routinely underestimate how large a genuinely compelling product or media property can become and how much the market can expand once people truly care, so short-term numbers should not be the sole guide to long-term ambition.

Reflection Questions:

  • Where might I be using current metrics or early traction as an excuse to think small about something that users clearly love?
  • How would I plan differently if I assumed my best project could be 5-10 times bigger than I currently believe, provided I stick with it?
  • What experiments or investments am I avoiding because I'm unconsciously capping the potential upside in my mind?
4

Crafting a compelling narrative about your work-framing it as culture-changing, excellence-driven, or uniquely meaningful-helps attract and retain talent, sustain morale through hard times, and differentiate even mundane products.

Reflection Questions:

  • If I had to explain my current project as something that could genuinely change a small corner of culture, what story would I tell?
  • How might reframing my team's day-to-day tasks in terms of a larger mission affect their motivation and persistence during setbacks?
  • What specific language or metaphors could I start using in meetings, emails, or pitches to better capture the deeper purpose of what we're building?
5

Cultivating heightened observation and curiosity-asking the questions others skip over and noticing small absurdities or patterns-is a transferable superpower across comedy, investing, company-building, and scientific research.

Reflection Questions:

  • What recurring situations in my life or industry do I accept as "just the way things are" that might actually deserve deeper questioning?
  • How could I build a simple habit (like a daily notes file) to capture odd, interesting, or funny observations before I forget them?
  • In which current problem or decision could I deliberately pause and ask, "What's the question here that nobody else seems to be asking?"
6

Knowing when to stop-respecting proportion and resisting the temptation to overextend a successful run-can be as important as getting started, preserving quality and legacy instead of diluting them.

Reflection Questions:

  • Where in my work or personal life am I continuing something mainly because it's working or paying well, even though the quality or joy is declining?
  • How might my long-term reputation or satisfaction improve if I chose to end or scale back a project at its peak rather than riding it into mediocrity?
  • What criteria could I define now (metrics, feelings, milestones) that would tell me it's time to gracefully exit or conclude a current endeavor?

Episode Summary - Notes by Hayden

We react to Bill Ackman's advice to young men
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