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My First MillionI spent a week meeting NYC's elite. Here's 5 lessons they taught me.
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Five lessons from a week with NYC’s business and creator scene
Shaan returns from New York City energized, calling it one of his most fun business trips, and tees up five “key phrases” he wants to unpack. Sam frames NYC as an exciting place to live and takes pride in showing it off as they decide where to start.
- •Shaan shares he hadn’t been to New York in about 10 years and just spent a week there
- •They set up five themes to discuss: trust, marketing, proximity, city brands, and “what does it really mean?”
- •Sam describes wanting to be a “steward” for NYC—showing it can be awesome without performing NYC identity
- •They choose to begin with the lesson on proximity
Lesson: Proximity — Hasan Minhaj’s office and the “covalent bond” of working close
Shaan recounts visiting Hasan Minhaj’s office and observing how a top creative runs a tight, work-focused environment. Hasan argues that fancy offices miss the point; the real work is the legal pad, sticky notes, and people being physically near each other.
- •Hasan dismisses glossy office signals and points to handwritten scripting and wall planning as “the work”
- •He describes proximity as a “covalent bond,” emphasizing atoms “bumping into each other” to create good outcomes
- •He invites people to use the space for work, meetings, or production needs to increase productive collisions
- •Shaan contrasts the density of NYC with his more dispersed work life and says he misses high proximity
Stacking meetings vs quiet time — maker/manager schedules and the Dunkin’ writer’s room
The conversation pivots from the benefits of proximity to the need for deep, uninterrupted work time. Shaan shares Hasan’s approach: stack intense in-person days and protect multiple days for solitary creative output.
- •Hasan’s team is still working late at night; Shaan arrives around 9:30–10:00 PM and they work for hours
- •Hasan ‘stacks’ meeting days back-to-back to preserve several quiet days afterward
- •He uses a minimal writing room above a Dunkin’ Donuts for focused, offline writing
- •They discuss maker time vs manager time and the need for long blocks to reach flow state
Sam’s proximity habits — “managing by wandering” and a barbell approach to work
Sam explains how he designs his office life to benefit from proximity while still protecting concentration. He describes walking around to observe and learn, then returning to quiet work—mirroring Shaan’s “barbell” framing.
- •Sam uses a recording light to prevent interruptions and keeps it on often to protect focus
- •He repeatedly walks the office to listen in on conversations and occasionally drops into meetings silently
- •He references “managing by wandering” as a way to stay grounded in what’s really happening
- •Shaan describes the ideal as extremes: high-contact proximity plus isolated deep work, avoiding the ‘weak middle’ of shallow Zoom/Slack work
Lesson: “What does it really mean?” — extracting the real lesson instead of the easy one
Shaan argues that repeated insights matter because they often still haven’t been fully understood. He tells a dinner story where someone claimed they “learned so much” from failure but couldn’t articulate the true lesson, reinforcing the importance of pressing for meaning.
- •Shaan values recurring lessons and believes repetition signals high importance
- •He retells a dinner moment where a failed entrepreneur couldn’t explain what they actually learned
- •Chris (from Tiny) challenges people to name the real takeaway, not a superficial detail
- •Shaan frames “what does it really mean?” as a question people don’t sit with enough
Inside Gary Vee’s orbit — Nick Dio and the craft of “social slack”
Shaan describes meeting Nick Dio, portrayed as Gary Vee’s right-hand man who hosts and connects people even when Gary isn’t present. Nick explains his real job as spotting the room’s “social slack” and elevating the experience by making subtle, high-leverage interventions.
- •Nick describes being seen as someone who just parties, then clarifies what he actually does
- •He claims every social room has “slack” (temperature, music, awkward gaps, unconnected groups) that can be improved
- •His goal is to make the room better in ways people may not consciously notice
- •Examples include relationship-building that influences where celebrations happen and meeting many people in emerging areas with no agenda
Sam’s update about Ben Wilson’s cancer and how listeners can help
Sam pauses the episode to share that former producer Ben Wilson has publicly announced he’s battling cancer and set up a GoFundMe. He encourages listeners to look Ben up, watch his video about the diagnosis, and support or help if they can.
- •Sam explains Ben Wilson is a former early producer and hosts his own podcast
- •He shares Ben’s cancer diagnosis details as Ben described them publicly
- •Sam directs people to Ben’s Twitter for the GoFundMe and additional information
- •He highlights a line from Ben about living and encourages support and awareness
Trust as a service — creators, food recommendations, and the coming “peak fakeness”
Shaan explains why trust stood out during NYC’s constant “hottest restaurant” recommendations and uses creator Jack’s Dining Room as a case study. He argues that as content becomes easier to fake, trusted curators become more valuable, and he pitches turning that trust into a scalable product.
- •Shaan meets Jack (Jack’s Dining Room / Yes Chef) and describes his hook: showcasing ‘the best’ food in places
- •He argues trust will become scarcer as ads, deepfakes, and AI-generated influencers proliferate
- •He compares a trusted creator’s recommendations with Yelp, saying Yelp is the default but not deeply loved or trusted
- •Shaan pitches building a ‘Jack’s List’ app—minimal, curated top picks per city and category—and offers to build it if they’ll lend name/face
AI in everyday life — Sam’s Suno songs, ‘Noah Flan,’ and explicit teaching for kids
Sam shares how he uses AI music generation to create custom songs for parenting, including a potty-training anthem. The hosts riff on prompts, saved AI “characters,” and how direct language can help kids learn—even if it feels uncomfortable to adults.
- •Sam describes subscribing to Suno and creating a folk-style potty-training song parodying ‘Let It Go’
- •He plays part of the song and explains how it helps his daughter use the potty
- •Shaan suggests using “Americana” in prompts to shape the musical style
- •Sam notes kids’ books and learning often require explicit detail that adults might avoid
A personal aside — Shaan praises Sam’s parenting and their ‘talk to them like adults’ approach
Shaan shares he was impressed seeing Sam as a dad during the NYC trip and calls him a great father. They discuss treating kids like adults at meals, including skipping the typical ‘kid menu’ mentality.
- •Shaan compliments Sam’s parenting and says he was touched observing it firsthand
- •Sam says he works hard at being a good dad and describes it as a mission
- •They reference advice Sam attributes to his mom: talk to kids like adults and feed them like adults
- •Shaan recounts being surprised by Sam’s daughter confidently asking for food at dinner
Lesson: Marketing — ‘steak so soft you can eat it with a spoon’ and other memorable one-liners
Shaan shares marketing lines he collected in NYC, especially from restaurants, and why concise phrases can do what long explanations can’t. Sam adds how these story-driven details create brand value that pure numbers-focused thinking can miss.
- •A steakhouse uses theatrical storytelling and a ‘treasure chest’ presentation to sell the experience
- •Shaan highlights the line: the steak will be so soft ‘you can eat it with a spoon’ as a ‘marketing kill shot’
- •Another restaurant’s proof point: ‘Taylor came here two nights in a row’
- •Sam’s spontaneous denim line ‘history you can wear’ becomes an example of strong positioning language
Branding as a moat — owning a word, positioning, and why it’s hard to do well
They broaden from anecdotes into how branding works: associating with a single idea or word over time. Sam references business reading and conversations that reinforced the importance of positioning, while Shaan emphasizes distillation and the difficulty of executing consistently.
- •Sam recounts learning from Peter Thiel’s view that branding can be a moat, even if he didn’t know how to do it
- •Sam cites Aaron Levie recommending ‘Positioning’ and related marketing books as core business reading
- •Shaan discusses distilling what something ‘really is’ (e.g., a brand owning a simple association)
- •They debate books vs studying real-world examples; Shaan says frameworks help but ground-truth swipes matter
‘Make chicken great again’ — reframing an Indian sauce brand through positioning and customer reality
Shaan tells a dinner story about an Indian restaurant group expanding into sauces and how a single positioning insight changed the perceived market. The reframing shifts from ‘cooking Indian food at home’ to making everyday chicken taste great, with implications for distribution and messaging.
- •Shaan explains why he initially doubted the sauce idea: he wasn’t sure how often people cook Indian food at home
- •He recounts how Rohan Oza helped reposition the product toward improving everyday chicken meals
- •They discuss how positioning is strategy that affects everything, including which supermarket aisle you belong in
- •Sam connects the concept to copywriting: specificity and empathy make messaging resonate
Quiet thoughts said out loud — decluttering, hidden anxieties, and making ideas stick
They explore why certain messages instantly change behavior by naming private feelings people don’t articulate. Shaan shares how decluttering creators shifted his wife’s mindset by speaking to shame and panic triggers, while Sam connects it to consumerism, visualizing waste, and how sticky ideas work.
- •Shaan describes his family’s decluttering struggle and how his wife changed her feed to follow decluttering coaches
- •A creator’s framing—panic about guests coming over and constant mental load—triggered a mindset shift
- •Sam relates, shares his own clutter frustrations, and notes how easy online buying fuels accumulation
- •Sam recommends ‘Made to Stick’ for frameworks; Shaan says books can be dated and advocates building a personal swipe file from real examples
