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My First MillionI Threw A Party With San Diego's Most Interesting Millionaires (#405)
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Founder weekend in San Diego: the setup and the luxury Airbnb playground
Shaan recounts an annual founder-friends weekend trip and explains the format: a small group rents an Airbnb and spends time hanging out. He describes the San Diego house they stayed in, owned by Mark, and the overbuilt “destination” amenities that made it a perfect spot for sports and bonding.
- •The group does a founder/friends hangout trip once or twice a year
- •They rent a San Diego Airbnb owned by Mark, who built a luxury short-term rental portfolio
- •The house is designed as an experience, with extensive backyard sports and leisure amenities
- •The first day is framed as sports-heavy bonding with business talk in between
The invite list comes from a tweet: curating a ‘cool people’ house party
On the second day, Shaan tweets asking who’s in San Diego and Ben curates a list of people to invite over. Shaan frames the experience as unusually social for him, emphasizing how energizing it felt to meet interesting builders in person.
- •Shaan tweets to find locals; Ben curates about 15 invitees
- •Shaan jokes this segment is basically “Shaan leaves the house”
- •The party is positioned as a high-signal room of builders across very different domains
- •The setting enables spontaneous conversations and introductions
Young builders and D2C operators: NFTs, gel blasters, and the mini-katana playbook
Shaan describes the mix of entrepreneurs who show up, including young NFT founders and direct-to-consumer operators. He highlights examples of rapid growth, unusual business constraints, and how creators adapt when traditional advertising channels aren’t available.
- •Two young NFT project owners with major sales attend; one recently revealed his identity
- •A D2C founder built gel blasters into tens of millions in revenue quickly and tells a conflict story with a big toy company
- •Isaac (the mini katana founder) shares how the business grows without paid ads due to platform restrictions
- •Shaan emphasizes how surreal it is for a listener-turned-guest to hear their business discussed on the show
The former CIA operator: rapport-building, charm, and why stories captivate rooms
A former CIA operative attends, and Shaan and Sam discuss what makes him so compelling in person. Shaan shares a conversation about long-term rapport building and how the operative uses information and patience, while Sam notes the person’s charisma and “it factor.”
- •A former CIA operative attends; Sam says they recorded an unreleased interview because of sensitive details
- •Shaan asks how someone builds influence; the operative describes long rapport-building and tracking wants/needs
- •Sam describes the operative as highly likable and captivating as a storyteller
- •Shaan describes repeatedly pulling people over to hear stories and learning how delivery drives attention
Ramon’s citizenship celebration and the best icebreaker: “weirdest way you tried to make a buck”
Ramon arrives with his son, and the group celebrates his U.S. citizenship with a cake and jokes about the message. Shaan explains why typical “what do you do?” talk becomes scripted, and how their chosen icebreaker creates better, less status-driven conversation.
- •Ramon becomes a U.S. citizen; the group buys a cake and celebrates with his family
- •Shaan explains why “what do you do?” makes successful rooms feel performative and one-uppy
- •They use an icebreaker: the weirdest way you tried to make money
- •Shaan describes Ramon as quiet until prompted, then an endless source of surprising stories
Ramon pretends to be an electrician—and learns the real lesson: subcontracting and honesty
Shaan retells Ramon’s story of taking an electrician job without knowing anything about electrical work and showing up in a costume-like outfit. After realizing he can’t do the work, Ramon admits the truth, and the client unexpectedly teaches him to subcontract and keep a margin—leading to a real contracting business.
- •Ramon widens his “painting” offer into a general ‘fix anything’ pitch and gets an electrician request
- •He shows up with a vest and clipboard, pretending to understand technical jargon
- •After failing to decode his notes, he returns and admits he can’t do the job
- •The client respects the honesty and teaches him to subcontract specialists and keep a margin
Resilience and repeated reinvention: from early wins to setbacks and rebuilding
The conversation expands from Ramon’s contractor origin story into a broader theme of bouncing back. Sam and Shaan outline how Ramon has built, lost, and rebuilt multiple times, and Shaan describes challenges in physical-goods economics and a later pivot that restores momentum.
- •Sam says Ramon made substantial money in contracting before immigrating and trying other ventures
- •Shaan describes Ramon’s current business selling pet products and how shipping costs spiked and hurt margins
- •Shaan describes Ramon pivoting from dog products to a cat litter product called Genius Litter
- •Shaan highlights a major distribution win: a nationwide PetSmart deal and Ramon’s persistence
Why storytelling wins in high-achiever rooms—and the self-deprecating rule
Shaan distills a key takeaway: in a room full of impressive people, storytelling separates who becomes memorable and who doesn’t. He contrasts facts-only intros with engaging narratives, and notes that stories centered on self-glorification push people away, while self-aware stories pull them in.
- •Shaan observes that storytelling—not raw achievement—drives connection and follow-up help
- •Facts-only explanations fall flat compared to stories with tension and humor
- •He notices ‘I’m awesome’ stories repel, while self-deprecating stories attract
- •He cites a rule shared at the party: only tell stories where you look like an idiot
Life-phase perception: play in youth, delusion in your 20s, analysis in your 30s, lanes in your 40s, contribution in your 70s
Shaan and Sam compare how different ages approached life and ambition across the weekend’s mix of attendees. They describe how kids optimize for play, twenty-somethings radiate confidence, thirty-somethings weigh opportunity costs, forty-somethings prioritize health and enjoyment, and older adults focus on family, contribution, and liveliness.
- •Kids focus on constant play and curiosity; Shaan notices learning energy as well
- •People in their 20s project ‘this will be massive’ confidence and benefit from constructive delusion
- •People in their 30s have self-belief but feel the high cost of choosing the wrong path and can over-analyze
- •People in their 40s ‘know their lane,’ value compounding, and prioritize health, family, and enjoying the journey
- •A couple in their 70s emphasize philanthropy, family, and appreciating having visitors around
Twice-a-year frame breaks: meeting different operators and seeing a luxury Airbnb as a business
Shaan calls the weekend itself a “frame break” and argues that experiences like this reset assumptions about what’s possible. The house functions as a business as much as a venue, and Shaan suggests that regularly immersing yourself in different life models changes how you think.
- •Shaan says the luxury Airbnb itself is a business and changes how you view opportunity
- •He emphasizes the importance of periodically ‘breaking your frame’ through new environments and people
- •Sam agrees the weekend sounded energizing and suggests doing it regularly
- •They transition from the weekend to a discussion about other frame-breaking experiences
Selling a company and living inside a buyer’s world: speed vs. distribution and why big companies move slowly
Sam asks what it’s like to be a founder whose company is now owned by someone else, and shares lessons from his time at a large organization. Together they discuss why building from scratch is rare, how bureaucracy can create predictability, and why size brings distribution but reduces speed while making mistakes more costly.
- •Sam argues ‘exit plans’ can be valid and building to sell isn’t inherently wrong
- •He says small focused teams can outbuild large teams because internal politics and incentives slow creation
- •Shaan observes progress velocity slows post-acquisition, even if other things improve
- •Sam notes bureaucracy can create redundancy and predictability, lowering anxiety
- •Shaan frames the core trade: big companies have distribution and size, but trade away speed; carefulness becomes a feature because mistakes are expensive
Bad ideas that become great ideas: picking projects, evolving the concept, and the ‘pimply to prize’ analogy
They discuss how many successful projects begin as illogical or unimpressive-sounding ideas because founders can act without needing approval. Shaan shares an older entrepreneur’s analogy about ideas transforming over time, and connects it to how The Hustle evolved from a conference into a newsletter that grew far beyond initial expectations.
- •Sam argues many great products start as ‘stupid’ or illogical experiments enabled by founder freedom
- •Shaan shares an older entrepreneur’s analogy about ideas looking unappealing at first but transforming with iteration
- •Shaan recounts how The Hustle started as a conference, then pivoted into content and a newsletter
- •They note that early perceptions of what can be ‘big’ are often wrong as the concept evolves
What changes after acquisition: hiring up, long-term planning, less panic—and a gym metaphor for poise
Shaan compares his scrappy approach to the post-acquisition approach: more hiring, more growth investment, and calmer decision-making. The conversation closes with a lesson about slowing down under stress—using a weightlifting metaphor—and how that mindset shift carries into business leadership.
- •Shaan notes the new owners added writers/editors and take a longer-term view than the original lean team
- •He describes three differences: more hiring, more money into growth, and less panic
- •Sam reflects on emotional reactivity and reframes calmness as maturity
- •Shaan shares a trainer’s lesson: the hardest reps are where gains happen, and the right response is poise not rushing
- •They frame this as personal growth in how Shaan handles pressure
How to hire a researcher: use paid trial projects and evaluate ‘frame, talking points, take’
Sam asks for help choosing among hundreds of researcher applicants, and Shaan outlines a practical selection process. Instead of interviews, Shaan recommends testing consistency over multiple weeks and judging whether candidates can turn raw nuggets into show-ready segments with a clear frame, supporting bullets, and a takeaway.
- •Shaan recommends selecting via project work rather than interviewing large numbers of candidates
- •He suggests paying for a short trial and testing consistency over multiple weeks, not just a single strong submission
- •He shares a research template: propose a frame, provide supporting talking points, and articulate the takeaway
- •They discuss how even imperfect framing helps because it’s better than starting from a blank page
- •Shaan closes with a ‘tricks of the trade’ anecdote about learning insider techniques from a TV show
