By playing, you agree to uListen's Terms and Privacy Policy and YouTube's Terms of Service.
My First MillionThe 12 Awards Of 2023: No.1 Unsexy Business, Wildest Predictions & More
Summaries, chapters, transcripts, and FAQs on this page are made by uListen, not YouTube.
Great conversations run long. Their best ideas don't have to.
uListen is free on iPhone, iPad, Android, Chrome, and Claude.
See howCHAPTERS
Jump to publisher timestampsChapter summaries
Part 2 setup: categories, “delusional” and unsexy businesses
Shaan tees up part two of the Milly Awards and previews the mix of categories they’ll run through. He frames the tone: a blend of funny superlatives, investing lessons, and under-the-radar business ideas.
- •Part two of the Milly Awards kicks off with multiple categories
- •“Most delusional person” and “Unsexy Business of the Year” are highlighted as favorites
- •They’ll also cover best content, predictions, coolest moment, and breakout of the year
Most delusional person: Elon/Zuck moment and Sam’s pick, Val
Sam opens with the easy “delusional” pick (Elon Musk) but chooses Val instead, describing him as unusually calm while doing aggressive, high-output business building. Sam is struck by Val’s scale, risk tolerance, and unconventional work schedule.
- •Sam recalls the Elon vs. Zuck near-fight as a funny “delusional” moment
- •Sam chooses Val as his real pick, describing his immigrant background and multiple businesses
- •Val’s calm logic and comfort with risk stand out to Sam
- •Sam shares Val’s extreme schedule and mentions he has five kids
“Sanest billionaire” inversion: meeting Michael Dell and the unexpected sports team story
A speaker can’t settle on a “crazy” person and flips the category to the most boring/sane person: Michael Dell. They recount meeting Dell, being surprised by how steady and unflashy he seemed, and share an anecdote about him ending up owning a pro sports team after a borrower defaulted.
- •A speaker names Brian Johnson as “crazy,” then inverts to “sanest” person: Michael Dell
- •They describe Dell as extremely calm and low-drama despite massive wealth
- •Dell claims limited extravagance (a few houses and a plane)
- •Anecdote: private credit lending led to Dell owning a professional sports team after a default
- •Sam and Shaan debate whether Dell’s calm persona can be fully trusted
Shaan’s “delusional” pick: AI-grown food + a plan to bring 10,000 engineers/lawyers to the US
Shaan describes a call with a highly energetic founder who wants to use AI to grow more mineral-rich food and also build a visa pipeline to bring large numbers of Turkish engineers and lawyers to America. Shaan is impressed by the ambition, the detailed plan, and the unusual combination of projects.
- •Shaan recounts meeting a founder introduced by Ben and being drawn in immediately
- •Founder claims American food quality is poor and wants to use AI/ML to improve crops
- •He describes training a GPT-like model on scientific papers to improve mineral content
- •Shaan raves about mineral-rich dried berries the founder sends (kids love them)
- •Founder outlines a systematic visa + income-share model to bring thousands of Turkish professionals to the US
Crazy ambition in one text: “a trillion dollars to ship 10 billion robots”
Sam reads a message from Brett Adcock that crystallizes the “crazy people think bigger” theme. The exchange contrasts Sam’s bootstrap framing with Brett’s gigantic scale assumptions.
- •Sam shares his ongoing fascination with Brett Adcock and his robot company
- •Sam asks if the business can work without raising much money
- •Brett responds that shipping 10 billion robots will cost just under a trillion dollars
- •Sam jokes about how small his thinking feels by comparison
- •Shaan riffs that Sam basically asked for a “newsletter version” of building robots
Best & worst investments: buying Letterboxd and the “money bonfire” podcast app
A speaker shares a best investment: buying a majority stake in Letterboxd after an informal coffee meeting in New Zealand. For worst investment, he describes buying a podcast app without a plan, struggling to staff it, and letting steady losses snowball for years.
- •A speaker meets Letterboxd founder Matt Buchanan in Auckland and ends up buying ~60%
- •He cites rapid growth to 10 million registered users and a ~$60M valuation
- •He compares owning social networks to owning “airports” that can monetize captive communities
- •Worst: buying the Castro podcast player without a clear operating plan
- •Founder departure, inability to find the right operator, and ongoing losses become a multi-year “money bonfire”
Sam’s investing wrap: a tiny project that pays his expenses and frustration with angel timelines
Sam names his best “investment” as a weekend-built copywriting product (copythat.com) that now covers his living expenses and serves as a creative playground. His worst is the experience of angel investing: lots of paper gains but no cash returns yet, plus limited control and patience required.
- •Sam built copythat.com as a small experiment; it ended up paying his living expenses
- •He likes having a playground project separate from partner/customer constraints
- •Sam has invested about $1M via angel investing since 2016 with no liquidity back yet
- •He dislikes the patience and lack of involvement despite markups on paper
- •A speaker shares an anecdote about early wins teaching the wrong lesson in angel investing
Shaan’s best deal: Shepherd—leveraging audience as an “unfair advantage,” plus deal structure lessons
Shaan picks Shepherd as his best investment and explains why: buying into a working business with tailwinds and then driving major lead flow through his audience. He also emphasizes how acquisition deal structure can drastically change outcomes, including a surprising financing detail in this deal.
- •Shaan explains his strategy shift: buy working businesses with tailwinds rather than inventing new ones
- •Shepherd benefited from remote work and later profitability pressures pushing offshore hiring
- •Shaan says their channels drove a huge portion of leads and the business tripled in 6–9 months
- •He frames the influencer + product combo as powerful when the underlying product is solid
- •Shaan describes a striking structure: he put little money down and the company effectively lent money for the stake
- •He contrasts venture’s standard terms with acquisition deals where structure can make or break returns
Biggest Ls: Shaan’s crypto tax timing + missed angel wins; Andrew’s dream house loss and public ticker pain
Shaan’s worst includes selling crypto for tax losses and delaying re-entry as prices rebounded, plus missing allocations in Whatnot and Shuffle. A speaker shares a major personal investing lesson from building a dream house that became exhausting and costly, then adds the emotional whiplash of seeing net worth swing daily via a public stock ticker.
- •Shaan regrets delaying re-buying Bitcoin after tax-loss selling as it rebounded
- •He says the real pain in angel investing is missing potential grand slams
- •He recounts wanting into Whatnot but not pushing hard enough; later it became very valuable
- •He also missed investing in Shuffle due to fund/legal constraints and describes it as high-variance upside
- •A speaker describes overbuilding a “forever home,” decision fatigue, and later selling at a 30% loss
- •He notes how public stock tickers make net worth swings visible and emotionally intense
- •He uses a Buffett “farm” metaphor to ignore noisy price signals
Managing a CEO: Sam’s Hampton learning curve and “non-fatal vs. fatal errors”
Sam describes his biggest operational challenge: learning how to work with a CEO day-to-day, especially when the business is tied to his reputation and he’s product-involved. A speaker responds with a framework: allow non-fatal mistakes to prevent resentment, and intervene only when errors become existential.
- •Sam says hiring a CEO isn’t the full solution; managing the relationship is hard
- •He describes slipping into bypassing chain of command when he wants to move fast
- •A speaker compares it to delegation: correcting everything undermines learning and ownership
- •They discuss allowing “non-fatal” mistakes but stepping in for “fatal” risks to the business or reputation
- •Sam frames the challenge as emotional as much as tactical
Unsexy Business of the Year: HVAC scaling and Pantone’s recurring revenue from color standards
Sam spotlights an HVAC company run by someone he knows from high school, describing rapid growth and operational innovations shared publicly. Another speaker picks Pantone, emphasizing how a boring standard can become a durable, high-revenue business through licensing and forced refresh cycles.
- •Sam highlights Hoffman Bros Heating and Cooling growth from $13M to ~$140M revenue (as shared in the thread)
- •He mentions cultural/operational moves like added holidays and “Hoffman University” training
- •A speaker chooses Pantone, describing standardized color books used across fashion and design
- •Pantone’s model includes trademarking/licensing colors and reselling books annually due to fading
- •They discuss Pantone also doing forecasting/trend work and how companies use these signals
Content of the Year: The Bear’s standout episode, speaking craft, hardship stories, and AI anxiety counterbalances
They each share their best content consumption: Shaan praises a specific episode of The Bear and recommends a speaking/presence book. Sam explains his theme of reading about hardship and charisma, highlighting a WWII documentary. Another speaker pairs an AI-focused book that argues for containment with a book about what stays constant over time, and they discuss why “survival” content can be oddly relaxing.
- •Shaan picks The Bear (Season 2, Episode 7) as a top TV moment and explains why it landed
- •Shaan recommends Talk Like Churchill, Stand Like Lincoln for speaking and presentation
- •Sam describes reading hardship narratives (including The Wager) for perspective and gratitude
- •Sam recommends Netflix’s World War II From the Frontlines, focusing on hardship and charisma/propaganda
- •A speaker recommends The Coming Wave alongside Morgan Housel’s Same as Ever to balance anxiety and perspective
- •They discuss watching Survivorman as a calming reminder of modern comforts
Wildest predictions: AI assistants reshaping admin work + revisiting last year’s calls
A speaker predicts assistant/admin work will be radically disrupted by AI systems tightly integrated with email, calendars, and documents. They review last year’s predictions, with some hits on the proliferation of GPT competitors, and Sam extends his Elon/Twitter prediction into the next year.
- •A speaker predicts AI will handle a large portion of assistant/admin tasks soon
- •They revisit prior predictions and note the rise of competing AI models and big-platform involvement
- •Sam revisits his Elon/Twitter expectations and extends the prediction forward
- •They mention Sam’s testing of Twitter ads and belief the experiment changes hands or ends under Elon
Coolest moment of the year: helping a friend buy a business, new parenthood, and a sold-out live show
Shaan’s coolest moment is helping his college friend Dan buy a business and seeing early success and renewed excitement. Sam names having a kid as his peak moment and describes how it changed his emotional baseline and relationship. A speaker picks the first live MFM event in Vancouver—nerves, a packed theater, and the feeling that “the nerds won.”
- •Shaan recounts guilt about leaving a friend behind earlier in life and later helping him buy a business
- •He describes Dan buying a bag-sales business serving major retailers and seeing strong early profit after debt payments
- •Sam says becoming a parent was the year’s coolest moment and describes the daily emotional impact
- •A speaker describes organizing the Vancouver live show, worrying about filling the venue, and seeing it sell out
- •They joke about refunding tickets to attendees and realize they could have charged
Breakout of the year: Ozempic/GLP-1, plus a favorite podcast tool—and closing remarks
Shaan names Ozempic as the breakout, describing its cultural reach and potential ripple effects. Sam agrees, recalls early exposure to semaglutide, and predicts both massive impact and eventual downsides. Another speaker picks Snipd, an AI-powered podcast player for capturing and resurfacing key moments, before they wrap the episode.
- •Shaan calls Ozempic a world-changing breakout and a “magic weight loss pill” moment
- •Sam recalls trying semaglutide early and sensing it reduced cravings broadly
- •Sam references the belief that GLP-1 may be bigger than ChatGPT in impact
- •A speaker recommends Snipd for transcript-based highlights and saving quotes while listening (including in-car)
- •They close out the Milly Awards and reflect on time passing into 2024
