My First Million Podcast Summary

Episode: We react to Bill Ackman's advice to young men
Hosts: Sam Parr & Shaan Puri
Date: November 20, 2025

Episode Overview

In this lively episode, Sam Parr and Shaan Puri kick things off by dissecting Bill Ackman's much-discussed advice to young men about meeting women: simply approaching and asking, “May I meet you?” The conversation spins into personal stories, relationship observations, and a joking brainstorm of formal pick-up lines. The second half explores bold entrepreneurship, the art of noticing opportunity, and lessons from MTV’s meteoric rise, with memorable detours into animation, AI, and how sensitivity drives genius in business and comedy.

Key Discussion Points & Insights

1. Bill Ackman’s “May I Meet You?”

(00:18–06:41)

• Ackman’s Advice: Bill Ackman suggested young men simply approach women and say, “May I meet you?” as a polite way to start a conversation, which he claims was rarely rejected in his youth.
• Hosts’ Reactions:
  • Shaan: Finds the politeness “hilarious,” compares Ackman’s use of Twitter to Magic Johnson’s obvious tweets, and questions if this line actually works.
  • Sam: Shares a much riskier pick-up line he used (“What’s the difference between a chickpea and a lentil? ...I don’t pay $500 to have a lentil on my face”) vs. Ackman’s formality.
    • "I made a joke about peeing on my face and it worked. Thank God I didn't say, 'may I meet you?'" (03:43 – Sam)
• Brainstorm: MFM Formal Pick-Up Lines:
  • “May I take your jacket?” - Generous, but possibly mistaken as staff.
  • “Are you cold?” - Leverages the idea that women are “always cold."
  • “Hey, I'm Bill Ackman. I'm the billionaire founder of Pershing Square. Nice to meet you.” - Could work with pre-work.

Memorable Moment:
Sam: “If a girl will reply to ‘may I meet you?’ I think that she's not someone I want to go out with.” (04:05)

Timestamps:

• Ackman’s Twitter advice: 02:16–03:43
• MFM brainstorm: 06:17–07:57

2. Boldness in Business: Street Interview Content as a “White Belt Business”

(11:09–16:28)

• Josh & Tabs Chocolate: Josh, at 19, began interviewing strangers in NYC parks for viral TikToks, eventually turning it into a $3 million/year business.
• Entrepreneurial “Starter Businesses”: Shaan calls this a “white belt business”—perfect for those starting out: low barrier, high hustle required, widely replicable.
  • “Anyone who's bold enough to go to one of these parks and walk up to someone at the age of 20 and build a company...” (12:51 – Sam)
• Man-on-the-Street Content Trends:
  • Example: "School of Hard Knocks" Instagram page, where mini-podcasting, man-on-the-street style, reaches millions.

Timestamps:

• Josh’s business origin & insight: 11:09–15:35
• Commentary on street-style content: 16:12–16:49

3. Lessons from MTV’s Origin Story & “Planting a Flag” in Business

(17:38–24:45)

• Tom Freston & MTV: The founders successfully bet on being different—hiring creative “misfits,” taking bold stances, and launching iconic shows (SpongeBob, Daily Show, Chappelle Show).
  • “Let's find the type of pot smoking guys in high school who sat in the back ... and have some character living inside their heads ... And we're going to crank these things out.”
    (19:23 – Sam reading Tom Freston quote)
• Takeaways:
  • Success comes from committing to a vision (“planting a flag”), not endlessly pivoting.
  • Personal examples: Calm’s founders focused on meditation through many experiments; The Hustle doubled down on email newsletters despite trend-chasing pressures.

Timestamps:

• MTV’s wild early days: 17:38–20:11
• Business “flag-planting”: 21:26–24:45

4. Underestimating the Upside / Art of the Grand Vision

(24:45–29:11)

• Entrepreneur Mistake: Both hosts discuss underestimating how big their projects could get—Morning Brew, Calm, and Barstool turned into hundred-million-dollar brands.
• Pandora’s Founder Speech: Sam recounts how Tim Westergren motivated his team to work years without pay, invoking purpose (“what we've created... is going to change culture”).
  • “When this thing finally finds its home, it's gonna change culture. How many times in your life can you say that you’ve had a chance to do that? That's what this is about.” (28:30 – Tim Westergren via Sam)
• Elon Musk as a Master of Grand Narrative:
  • Transforms business missions (SpaceX, AI, even personal life events) into civilization-scale stories.

Timestamps:

• The Hustle’s “pirate ship” vision: 24:05–24:45
• Pandora founder story: 26:18–28:30
• Musk’s “grand scale” framing: 28:30–29:11

5. The Art of Taking Ideas Seriously

(31:10–33:27)

• Success often comes from taking a simple idea way more seriously than others—even if the domain seems “silly” or is overlooked (cartoon creation, newsletter writing, hosting cocktail parties).
  • “Everybody who's successful in life has just taken a simple idea very seriously. Way more seriously than you would expect.” (31:10 – Shaan)

6. Creativity, Animation, and New-Gen Storytelling

(35:02–38:42)

• SpongeBob & Modern Animation: Passion projects can become massive; creators like “Amazing Digital Circus” (400M+ YouTube views per episode) thrive using new tools (game engines) and self-directed distribution.
  • “They created this show on YouTube and it gets hundreds of millions of views every episode ... on every single episode!” (36:24 – Shaan)

7. Sensitivity as the Root of Genius (Comedy, Investing, Tech)

(44:46–50:06)

• Ben Horowitz & the Art of Noticing: After a Ben Horowitz interview, hosts discuss how top performers ask first-principles questions others ignore, e.g., “Why did slavery ever end?” and draw insights from history.
• Eddie Murphy’s Sensitivity: Murphy claims top comedians are simply “more sensitive” and notice what other people overlook.
  • “We are just more sensitive to everyone and so our threshold of like something that grabs us is lower.” (47:00 – Sam paraphrasing Murphy)
• Great Investors as Observers:
  • Warren Buffett reads financials to “just notice” what stands out, looking for the unnoticed opportunities others miss.

8. The Noticing Muscle—Business, Comedy, and AI

(51:14–53:48)

• Observational Power:
  • Seinfeld-style “everyday observations” can be a wellspring of opportunity or humor.
  • In AI, “outsiders” noticed breakthroughs that insiders missed—the attention mechanism paper at Google wasn't exploited by Google, but by DeepMind, OpenAI, etc.

Memorable Quote:
“Comedy is the art of noticing.” (48:00 – Shaan)

9. On Proportion and Knowing When to End

(53:48–54:31)

• Jerry Seinfeld’s Wisdom:
  • Quoted by Shaan: “The most important word in art is proportion. ...Getting proportion right is what makes it art or makes it mediocre.”
  • Turned down $110M for one more Seinfeld season because the right amount matters.

Timestamps:

• Seinfeld quote: 53:48–54:31

Notable Quotes & Memorable Moments

• On Ackman’s Line:
  “May I meet you?... I don't know how you say this, but may I meet you? Before engaging further in conversation. I almost never got a no.” (02:45 – Shaan paraphrasing Bill Ackman)
• On Business Boldness:
  “This is one of the best examples of a just get-in-the-game business.” (15:24 – Shaan on street interviews)
• On Planting a Flag:
  “When you use this product, we all know how magical it is. It will find its home.” (28:30 – Tim Westergren, as told by Sam)
• On Sensitivity and Comedy:
  “We are just more sensitive to everyone and so our threshold of like something that grabs us is lower.” (47:00 – from Eddie Murphy via Sam)
• On Taking Ideas Seriously:
  “Everybody who's successful in life has just taken a simple idea very seriously. Way more seriously than you would expect.” (31:10 – Shaan)
• On Art and Proportion:
  “The most important word in art is proportion...Getting proportion right is what makes it art or makes it mediocre.” (54:29 – Jerry Seinfeld, quoted by Shaan)

Topical Timestamps (Quick Reference)

• Bill Ackman/May I Meet You?: 00:18–07:57
• Street Interview Business: 11:09–16:49
• MTV/“Planting Your Flag”: 17:38–24:45
• Undervaluing Your Own Potential: 24:45–29:11
• Animation’s New Wave: 35:02–38:42
• Ben Horowitz & Sensitivity: 39:36–47:00
• The Art of Noticing/Investing/Comedy: 47:00–51:14
• AI & Outsider Insight: 51:14–53:48
• Seinfeld on Proportion: 53:48–54:31

Conclusion

This episode is rich with sharp insights, wry humor, and big-thinking optimism. Parr and Puri move deftly from the comedy of dating advice to profound reflections on entrepreneurship and artistic discipline, always circling back to the same mantra: See what others ignore. Take simple ideas seriously. Stay curious, plant your flag, and above all, know the value of proportion.