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Milly Awards setup: what the episode covers and why it’s a two-parter
Shaan explains the premise of the Milly Awards and previews the categories they’ll cover in part one versus part two. The group gets into the festive tone—dressing up, teasing each other, and setting expectations for a long, category-driven episode.
- •Shaan frames the Milly Awards as the show’s annual, most popular episode with many categories
- •Preview of part one categories (including “Billy of the Year,” biggest change for 2024, best business idea, and more) and part two categories
- •The hosts banter about dressing up and being “dapper” as they begin
Category: Favorite MFM guest/episode — Sam’s pick (Kevin Ryan) and why it stood out
Sam names Kevin Ryan as his top guest of the year, while also mentioning Scott Galloway as a close contender and referencing the backlash to a viral clip. Shaan highlights how Kevin Ryan shared unusually specific details about how he structures companies for tax efficiency.
- •Sam chooses Kevin Ryan as his favorite guest, praising his wisdom and balance
- •Sam mentions Scott Galloway and a viral clip where viewers criticized how “depressed” they sounded
- •Shaan notes Kevin Ryan openly discussed company structure and tax-minimization strategy in unusual detail
Category: Favorite MFM guest/episode — Andrew’s pick (Sarah Moore) and the follow-up verification
Andrew picks Sarah Moore, describing her life story and why it felt more realistic and tactical than typical tech success narratives. The group jokes about her saying she wanted to stay low-key despite the episode’s popularity, and Shaan shares that he met her afterward because he initially worried the story sounded too good to be true.
- •Andrew praises Sarah Moore’s story as relatable, simple, tactical, and “not rocket science” for learning business and buying a company
- •They discuss how the episode became one of their most listened-to despite her desire to stay under the radar
- •Shaan admits he worried the story might be fabricated, then explains meeting her in person and feeling it checked out
- •Shaan says she received outreach from entertainment outlets after the episode
Category: Favorite MFM guest/episode — Shaan’s pick (Connor Price) and a shift in marketing strategy
Shaan selects Connor Price and explains why the episode changed how he thinks about modern marketing. He describes a progression from interruption-based ads to influencer ads to entertainment content where the product is embedded, and says this insight influenced how they changed their own ad approach.
- •Shaan tells Connor Price’s origin story: warehouse job to viral TikTok success, with his wife as a key driver/manager
- •Shaan lays out “era one” (interrupting ads), “era two” (influencer promotion), and a newer model where the product is integrated into entertaining content
- •He cites examples of product-as-payoff content and says once he noticed it, he saw it everywhere
- •Shaan says their own ad approach shifted toward entertaining segments that lead into the product
Category: “Billy of the Year” — what it means and Andrew’s pick (Charlie Munger)
They define “Billy of the Year” as someone “balling out of control” with swagger and a respected style of success. Andrew chooses Charlie Munger and shares a personal story illustrating Munger’s sharpness late in life, including a real estate partnership built in his 90s.
- •They define the award as celebrating a high-swagger, high-respect style of success (not necessarily a billionaire)
- •Andrew picks Charlie Munger and notes he stayed sharp up to the end of his life
- •Andrew recounts a dinner where Munger helped a younger associate on a deal in real time
- •Andrew says Munger mentored a neighborhood kid and together they built a very large Los Angeles apartment portfolio starting when Munger was around 90
Category: “Billy of the Year” — Sam’s pick (Palmer Luckey) and the appeal of bluntness
Sam names Palmer Luckey as his Billy of the Year, praising his willingness to say controversial things plainly. Sam cites Luckey’s remarks about kids’ career aspirations and why some “dreams” shouldn’t be encouraged, plus other colorful details that make him a compelling character.
- •Sam picks Palmer Luckey and describes him as a “loose cannon” who says what others won’t
- •Sam repeats Luckey’s line about kids wanting to be influencers/gamers and the idea that “you can’t tell kids to follow their dreams when their dreams suck”
- •He contrasts modern aspirations with a past era where kids wanted to be astronauts
- •They discuss Luckey’s distinctive style and persona, including his claims about flying commercial and sitting near the bathroom
Category: “Billy of the Year” — Shaan’s pick (Jesse Itzler) and a life built around adventures
Shaan picks Jesse Itzler and lists a rapid-fire set of reasons he admires his range of projects, family involvement, and adventurous philosophy. The group also references tension from a prior question about monthly burn and a memorable quote Shaan loves.
- •Shaan picks Jesse Itzler and highlights his multi-hyphenate track record across business and media
- •Shaan emphasizes Itzler being engaged as a dad and having an “adventure” philosophy
- •He references building varied projects (brands, events) and doing unusual challenges as part of his lifestyle
- •Sam notes Itzler once got upset at him over a question about monthly burn, and Shaan says they cut part of that exchange
- •Shaan calls out Itzler’s memorable competitive line: “Keep the money warm”
Category: Biggest change for 2024 — revisiting last year’s goals and Sam’s new phone reset
They recap what each person said they’d change last year and briefly evaluate how it went. Sam says he became less metrics-driven, then outlines new changes: a potential move and a plan to reduce phone addiction through grayscale mode and possibly switching to a dumb phone.
- •They recap last year’s changes: texting responsiveness, leadership style, and managing impulsiveness
- •Sam says he succeeded at being less metrics-obsessed and more “vibe” oriented
- •Sam describes experimenting with grayscale mode to reduce stimulation and exposure to bright colors
- •Sam says he wants a dumb phone to address phone addiction and set a better example for his kids
Category: Biggest change for 2024 — Andrew’s “break up with email” system and the tradeoffs
Andrew describes aggressively blocking distractions by removing email from his phone, limiting apps, and relying on tools that prevent bypassing restrictions. He then explains a new workflow where an assistant screens emails and sends only what’s essential, while also acknowledging the downside through a story about missing an email from Mark Zuckerberg.
- •Andrew discusses using blocking tools and removing fun apps, describing it as withdrawal-like
- •He explains a system where an assistant sends screenshots of only important emails for him to respond to
- •Andrew says email interruptions break flow state by pulling him into unrelated threads and subject lines
- •Shaan jokes about “printed email” as a luxury behavior; Andrew counters that the assistant approach can be accessible
- •Andrew tells a story about missing an email invite from Mark Zuckerberg because he wasn’t checking his phone, and how that still haunts the decision
Category: Biggest change for 2024 — social dynamics of paying the bill and Shaan’s “make space for great” philosophy
The conversation detours into dinner-bill etiquette, with Andrew explaining why he sometimes randomizes who pays to avoid status discomfort. Shaan then shares his own major change: shutting down “good but not great” profit streams to create space for better opportunities, including ending his course and winding down his rolling fund.
- •Sam criticizes the “everyone put a card in” approach; Andrew explains it avoids awkward power dynamics around money
- •Shaan says he turned off substantial profit streams because they were only “okay,” not great or fulfilling
- •Shaan names shutting down his writing course and stopping outside money in his rolling fund as examples
- •He explains the idea: if you want something great, you must create time and mental space by quitting “not terrible” commitments
- •Andrew agrees that fundraising can create obligations that interrupt the day, giving an example of an investor call breaking his creative flow
Category: Biggest change (continued) — Shaan admits failing his impulsiveness goal
Shaan gives an update on his prior goal to manage impulsiveness with a cooldown period before committing to new ventures. He admits he failed quickly—moving ahead within days—suggesting the same tendency is still at play.
- •Shaan describes setting a two-week cooldown to evaluate a business idea before committing
- •He admits he broke the rule after two days by landing the first customer and ramping up immediately
- •He frames it as a reminder that starting a business is a multi-year “marriage,” not something to jump into lightly
- •Shaan says he’s keeping the impulsiveness management goal on his list going forward
Category: Person you’d bet it all on — Sam’s pick (Austin Rief) and what he values
Sam weighs two choices and ultimately selects Austin Rief, describing why he’d invest in him blindly. He explains he values a balance of optimism and pessimism—big ambition paired with downside planning.
- •Sam debates between two guests, then chooses Austin Rief as the person he’d bet on
- •Sam references Austin’s track record and business outcomes discussed in the episode
- •Sam explains he values people who combine optimism with conservative downside planning
- •Shaan notes the irony of a former competitor becoming someone Sam admires deeply
Category: Person you’d bet it all on — Andrew’s pick (Andrew Huberman) as an “undisruptable” personal brand
Andrew argues that in an era of AI disruption, betting on a specific business is hard, so he’d bet on a person with a “personal monopoly.” He chooses Andrew Huberman, describing his audience trust, advertising power, and the strength of his brand as a business moat.
- •Andrew says AI makes business-level bets tricky due to cascading second- and third-order effects
- •He proposes betting on a podcaster with a strong personal brand and direct audience influence
- •He chooses Andrew Huberman and says the audience affinity makes advertising extremely powerful
- •Andrew calls the business largely undisruptable except for extreme personal risk
Category: Person you’d bet it all on — Shaan chooses Sam and defines the underrated trait: seriousness and focus
Shaan surprises Sam by choosing him as the person he’d bet everything on. Shaan explains the choice is less about raw talent and more about consistency, seriousness, and focus—contrasting it with “shiny object syndrome” that even Shaan admits he has.
- •Shaan picks Sam and says the deciding trait is focus and seriousness, not just intelligence or talent
- •He contrasts Sam with people who constantly switch narratives and chase shiny objects
- •Shaan cites examples of Sam taking each phase seriously, from early content to events to current projects
- •Shaan connects the idea to hiring operators who steadily execute rather than constantly chase trendy tactics
Category: Best business for someone else to do — privacy services, AI Tinder, and TikTok Shop opportunities (Part 1 finale)
They close part one with business ideas others should pursue: privacy protection services, an AI-driven gamified dating concept, and building products for TikTok Shop’s fast-growing affiliate ecosystem. Shaan frames TikTok Shop as a current “golden era” with visibility into what sells and strong platform incentives, then they sign off to continue in part two.
- •Sam proposes privacy-focused services that help remove/protect personal information online, starting with high-end customers and trickling down
- •Andrew pitches “AI Tinder,” a gamified dating experience with known-fake profiles and chat-based challenges, framing it as practice for social skills
- •Shaan argues TikTok Shop is a major opportunity because creators can affiliate products easily and the platform is heavily incentivizing sales
- •They discuss how TikTok Shop shows what’s selling and how many units, enabling fast iteration or competition
- •Shaan ends part one and directs listeners to part two for remaining categories
