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My First MillionCan You Get Rich with A Blue Collar Hustle? | My First Million Q&A (#457)
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Rapid-fire Q&A setup and Sam’s college banter
Sam and Shaan open with jokes about Sam’s university and the “last minute” nature of the episode. They explain the Q&A format, how they gathered questions, and the intent to keep answers short (despite teasing that Shaan will run long).
- •Sam riffs on Belmont University and pokes fun at its standards and cost
- •They decide to do a Q&A session with questions pulled from their tweets
- •They set an informal rule to keep each question around three minutes
- •Tone-setting: playful teasing between the hosts as they jump in
Sweaty startups vs internet businesses: choosing the problems you want
Sam and Shaan react to a question about “sweaty startups” (blue-collar or brick-and-mortar cash-flow businesses) versus digital businesses. They argue there are many ways to win, but emphasize choosing the path aligned with your lifestyle and preferred tradeoffs.
- •Sam says any path to making money is valid, but he prefers digital businesses due to lower capital needs and flexibility
- •Sam argues it’s typically harder to make $1M/year in brick-and-mortar than digitally
- •Shaan says the “don’t compete with Stanford grads” framing is a catchy but unimportant idea; attention and demand are the real challenge
- •Shaan contrasts operational headaches (staff call-outs, property issues) with the appeal of pushing a button to send a newsletter
- •They joke about “sweaty startup” influencers making money from digital products too
Great ideas that didn’t take off: a photo-request social app and buying homes online
They share examples of businesses they found compelling that ultimately didn’t work. Shaan describes a social app mechanic he still believes could work, while Sam discusses the persistent challenge of moving major purchases—especially homes—fully online.
- •Shaan describes Povio, where users request a photo and the app takes it immediately, shifting photos from “push” to “pull”
- •Shaan claims successful social networks win via changes in “privacy policy,” not features, and frames Povio as a clever shift
- •The app showed early campus traction but faded; Shaan still likes the underlying mechanic
- •Sam cites Doorsey and his belief that more big purchases will move online, with homes as a major category still unsolved
- •They discuss the idea that some categories are still more difficult to sell online despite broader e-commerce growth
What does “enough” look like? Money targets vs daily freedom
Sam explains why he feels there’s never a final amount of money that eliminates worry, while Shaan reframes “enough” as a lifestyle state. They compare ambition, craft mastery, and freedom from sacrificing today for an imagined tomorrow.
- •Sam says hitting financial milestones didn’t remove worry; the feeling resets over time
- •Shaan says instead of picking a number, he asks what he’d do if he already felt he had enough
- •Shaan quotes Naval’s idea of retirement as stopping sacrifice today for an imagined tomorrow
- •Shaan describes an “enough” day as doing activities where the act itself is rewarding (podcasting, coaching, writer’s room, teaching)
- •Sam reframes “never enough” as continual improvement in a craft, not perpetual dissatisfaction
Redoing college: mine the ‘gold mine’ of people, experiments, and practical basics
They discuss what they’d do differently in college, focusing less on grades and more on people, experimentation, and building skills early. Shaan emphasizes starting projects and leveraging networks; Sam focuses on school choice, exposure, and practical credit-building.
- •Shaan regrets being a “do nothing” student and says college is a gold mine for friends, partners, and customers
- •Shaan says he would have launched businesses on campus and leveraged alumni connections
- •They agree college is more about people and environment than classes and grades; Shaan argues students should “dabble” more
- •Shaan praises studying abroad and shares his time in Australia; Sam calls Sydney the greatest city for a 19-year-old
- •Sam regrets not taking high school seriously enough to attend a more diverse, globally exposed school
- •Sam wishes he built credit starting at 18 and explains how thin credit history affected a home purchase
When deals almost close (or don’t): expectations, retrades, and trust-building disclosure
Sam and Shaan swap hard-won lessons about acquisitions that stall or collapse. They describe how to emotionally detach, why big companies may be less likely to “retrade,” and how proactively surfacing risks early can accelerate trust or end a bad deal sooner.
- •Sam says most deals fall through; he acts like it will close but assumes it won’t to protect his mindset
- •Sam recounts learning in a big-company process that internal approvals create pressure to follow through
- •Shaan repeats the maxim that deals fall through by nature and stresses emotional detachment
- •Shaan claims every deal that closes has “two walkaway moments” before it’s done
- •Shaan shares advice from Balaji: discount offers that are earlier in diligence because closing probability is lower
- •Sam recommends revealing potential deal-killers early (“every reason you should not buy”) to build trust or exit quickly; Shaan says the buyers later praised this approach
Sara’s List update becomes “Sara’s Exodus”: avoiding zombie equity and overvalued unicorns
They explain the concept behind Sara’s List—joining safer, later-stage companies where stock could still meaningfully multiply—then pivot to why the more useful list now might be which companies to avoid. They discuss how 2020–2021-era valuations can trap employees in equity with little upside.
- •Sam defines Sara’s List as companies with safer jobs, strong benefits, and stock with meaningful upside potential
- •Shaan explains the idea via Sara’s experience joining already-large companies that still grew significantly
- •Shaan argues the current environment calls for “Sara’s Exodus”: identifying companies with underwater equity from peak-era fundraising
- •They propose checking which companies became unicorns in the 2020–2021 period and treating them skeptically until proven otherwise
- •Shaan suggests asking leaders about fair market value versus last valuation and how liquidation preferences can leave employees with nothing
- •They riff on tech-company perks and food culture with stories about Airbnb and Zynga cafeterias
Maintaining friendships at a distance: “no new friends” and limited bandwidth
Both admit they’re not great at sustaining friendships during busy life phases. Sam describes a strict prioritization approach, while Shaan explains he’s chosen to focus elsewhere for now and feels guilty about it.
- •Sam summarizes his current approach as “no new friends” and says no to most invites
- •Sam’s framing: if you’re already in, you’re in; otherwise, he’s not expanding the circle
- •Shaan says he’s a “shitty friend” right now and apologizes to friends for it
- •Shaan says limited bandwidth forces tradeoffs; he’s prioritizing being a great dad, making money, and getting in shape
- •They acknowledge the reality of phases of life affecting relationship maintenance
Quirky business ideas: selling status, D2C IQ tests, and a short-lived crystal brand
Shaan shares fascination with novelty businesses that sell symbolic status or identity, like naming stars or buying tiny land plots with titles. He also describes experimenting with an e-commerce crystal brand and why he now believes it was working better than he understood at the time.
- •Shaan cites examples of selling symbolic ownership/status (naming a star, being “knighted” with a land plot)
- •He’s drawn to playful one-off “stupid” business challenges like pet rock-style concepts
- •Shaan proposes a direct-to-consumer IQ test as a paid product people would buy for ego/curiosity
- •He describes launching a crystal e-commerce brand briefly and later realizing the unit economics were actually favorable
- •Sam questions the ethics; Shaan argues belief-driven products are “in the eye of the believer,” and shares celebrity references from magazines as demand signals
Early Hampton ‘big boy moves’: founder-led sales intensity and brand investment
Sam explains the earliest concrete actions that built Hampton, emphasizing speed, direct customer conversations, and closing the first sales. He also describes investing in branding and hiring leadership early once he saw the business could outgrow his personal skill set.
- •Sam bought a simple domain/page, drove signups, and personally interviewed every applicant
- •He says he did 100–200 customer interviews and ran back-to-back calls to close early sales
- •Sam claims he helped drive the first $1M in sales through relentless outbound and selling
- •He hired a CEO early because he believed the business would outgrow his capabilities
- •Shaan credits the name and branding; Sam explains paying for an agency and directing the aesthetic with old Rolex ads and “British racing green”
The three ‘small boy moves’: waiting, worrying, wanting—and locus of control
Shaan defines “small boy stuff” as mental patterns that keep people passive and dissatisfied, summarizing them as the three W’s. Sam adds the concept of internal versus external locus of control, and Shaan expands it with an analogy about a plant growing regardless of conditions.
- •Shaan’s three W’s: waiting to do what you want, worrying about what might happen, and wanting what others have
- •He praises a structured approach to worrying, referencing Sam’s “worry time” framework
- •Sam explains external vs internal locus of control as blaming circumstances versus owning outcomes
- •Shaan uses a plant metaphor to reject blaming soil, seed, sunlight, or competitors—emphasizing personal responsibility
- •They agree the “loser mentality” shows up when people over-index on external explanations
What each host admires about the other: calm positivity vs intensity and a personal code
They answer a listener’s question by naming each other’s best qualities and unpacking what those traits look like in practice. Sam praises Shaan’s steady positivity, while Shaan praises Sam’s ability to dial intensity to the maximum and his strong sense of loyalty and principles.
- •Sam says Shaan is consistently positive and hard to rattle, which contrasts with Sam’s more emotional temperament
- •Shaan credits Sam’s intensity as the common denominator behind fitness, The Hustle, and Hampton progress
- •Shaan describes Sam’s tendency to go “all in” with systems, accountability, and maximum effort
- •Shaan says Sam “has a code” around loyalty and showing up, even if Shaan doesn’t always agree with it
- •They discuss the idea of backing friends publicly even when you disagree privately
Creatorpreneurs worth watching: different play styles, output, and project selection
They define “creatorpreneur” and then name people they pay attention to, explaining what they admire: purpose, intensity, business-building skill, or style. Shaan emphasizes studying creators outside the usual business bubble and highlights the power of choosing the right business aligned with an audience.
- •Sam names creators he likes and explains what impresses him about their mindset, competitiveness, or execution
- •They agree Austin Rief is impressive and discuss how relationships can reshape prior competitive bias
- •Shaan says he studies creators in other categories to avoid becoming a copycat in the business creator bubble
- •He points to Dani Austin as an example of strong alignment between audience story and business choice
- •Shaan names Pomp for output, Tim Ferriss for brand discipline, and Steve Bartlett for style; Sam discusses why style can be hard to imitate
Bad roommates, messy rooms, and who’s having the most fun
They close with lighter personal questions: who they’d least want to live with and who seems to be enjoying life most. Their answers focus on living by your own terms, integrating work with genuine interests, and having fun without waiting for external milestones.
- •Sam says Elon Musk, Gary Vaynerchuk, and MrBeast would all be terrible roommates; Shaan jokes Elon would be best because he’d never be home
- •They talk about how successful people can have chaotic homes; Shaan admits his office is a disaster
- •Shaan asks who’s “having the most fun,” valuing fun over status metrics
- •Sam names Rob Dyrdek and Joe Rogan, praising fun-for-fun’s-sake and living on one’s own terms
- •Shaan adds Joe Rogan, Bill Simmons, and his Uncle Vinnie (“Smiley”) as examples of enjoying life now rather than postponing joy
- •They wrap by noting Q&As are easy and fun, and they should do more of them
Publisher timestamps
- 0:00Intro
- 1:40Sweaty Startup
- 6:34Most interesting startup that never took off
- 11:00What does enough look like?
- 18:30How would you do college differently?
- 23:33How to handle a deal not closing
- 33:07Updates to Sara's List
- 40:22Maintaining Friendships
- 41:16Quirkiest Business Idea
- 45:55First 5 Big Boy Moves at Hampton
- 48:573 Most Common Small Boy Moves
- 53:48Sam and Shaan's Greatest Quality
- 59:19Favorite Creatorpreneuers
- 1:05:30Who would you live with?
- 1:06:56Who is having the most fun?
