Dec 18, 2023 · 49m · my-first-million
The 2023 Milly Awards (#531)
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In Part One of the annual 2023 Milly Awards, Shaan Puri, Sam Parr, and Andrew Wilkinson celebrate standout entrepreneurs, dissect modern marketing strategies, and debate their biggest operational transformations heading into 2024.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. The hosts hold 73.8% of the talking time here. How this is scored →
The hosts as informed peer 5.6 Guest teaching 3.9 Guest disagreement 1.2 The hosts pushing back 2.1
speaking balance: gold is the hosts, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 27:50 Andrew defends credit card roulette
Andrew directly rejects Sam's critique of their dinner bill game, explaining the social dilemma wealthy individuals face when picking up checks.
Hardest push from the hosts ▶ 27:20 Sam confronts Andrew over credit card rouletteSam pushes back hard on Andrew and Chris forcing everyone to throw cards into the hat at an expensive dinner regardless of guests' financial standing.
Biggest teaching moment ▶ 12:25 Andrew shares Charlie Munger's side hustle real estate portfolioAndrew educates the hosts on Charlie Munger's sharpness late in life by detailing his billion-dollar apartment deals with a mentee.
The host holds their own ▶ 46:20 Shaan articulates the TikTok Shop arbitrage opportunityShaan illustrates strong entrepreneurial domain expertise by explaining how TikTok subsidizes products and acts as an affiliate distribution engine.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | The hosts as informed peer | Guest teaching | Guest disagreement | The hosts pushing back | Why |
|---|---|---|---|---|---|---|
| Opening Banter and Setting Award Categories | 6 | 5 | 1 | 2 | Shaan breaks down the Kevin Ryan tax minimization and QSBS structuring strategy in depth, while Andrew shares his perspective on the Sarah Moore eggcartons.com episode. The dynamic is collaborative and analytical without any friction. | |
| Favorite Guest: Connor Price and Modern Content Marketing | 7 | 1 | 0 | 0 | Shaan delivers an extended monologue analyzing Connor Price's viral music marketing strategy, categorizing the evolution of modern content advertising into three distinct eras. | |
| HubSpot Sponsor Commercial | 4 | 6 | 1 | 2 | After a brief commercial break, Andrew educates the hosts on Charlie Munger's sharp business acuity right before his death, sharing an insider dinner story about a billion-dollar Los Angeles apartment portfolio. | |
| Billy of the Year: Palmer Luckey | 5 | 2 | 1 | 3 | Sam nominates Palmer Luckey and Shaan champions Jesse Itzler, trading stories about founder mindsets. Shaan playfully calls out Sam for previously badgering Itzler on the podcast about personal finances. | |
| Biggest Change for 2024: Sam and Andrew on Digital Detox | 4 | 6 | 2 | 2 | Andrew shares his practical system for eliminating email access and explains how grayscale and red screen shortcuts mitigate screen addiction, offering technical advice to Sam. | |
| Rich Habits, The Zuckerberg Email, and Bill Roulette | 4 | 5 | 3 | 4 | Sam challenges Andrew on playing 'credit card roulette' during group dinners with people of differing net worths, prompting Andrew to defend why wealthy people end up in awkward social dining dynamics. | |
| Biggest Change for 2024: Shaan Eliminates Middle-Tier Revenue | 7 | 3 | 1 | 3 | Shaan explains his strategic decision to cut out $1.5M in middle-tier revenue streams to create space for bigger opportunities. Sam points out that Andrew's paid subscriptions slightly contradict this philosophy. | |
| Person You Would Bet It All On | 6 | 3 | 0 | 1 | The participants discuss individuals they would back blindly. Shaan gives a heartfelt pitch on why Sam's single-minded focus and seriousness makes him a superior operator over scattered talent. | |
| Best Business for Someone Else to Start | 7 | 4 | 2 | 2 | The group pitches startup opportunities including privacy services, AI Tinder bots, and TikTok Shop affiliates. Shaan demonstrates domain knowledge detailing TikTok's subsidy models and the Shadow Work Journal case study. |
Statements from this episode (13)
Puri: QSBS Trusts Allow Stacking Multiple $10M Tax-Free Capital Gains
“And you're getting QSPS, you know, the ten million dollars tax free. For you times each of your kids, I can get to fifty million tax-free if I got, you know, three or four kids or whatever.”
Wilkinson: Charlie Munger and his mentee built a $1B LA apartment portfolio
“Charlie backed him on this. And now they own a billion dollar real estate portfolio of Los Angeles apartments.”
Sam Parr: Palmer Luckey says what billionaires are too afraid to say
“He says what you want to say if you were a billionaire, but you'd be too afraid to say it.”
Puri: My First Million edited out awkward exchange with Jesse Itzler
“We had to cut it out of the episode because he got so awkward.”
Wilkinson: Offshore virtual assistant handles email management for $1,000 monthly
“So I have an assistant in the Philippines, and it's like a thousand dollars a month, and she does it, right? So it's like, it is something that a lot of people could be doing.”
Wilkinson: Wealth creates a lose-lose social dynamic when dining bills arrive
“There's this weird dynamic that happens where when the bill comes, if you pay the bill, you're showing off, or you're implying they can't afford it, and if you don't pay the bill, you're an asshole because you can afford to, and so that's why we do that.”
Shaan Puri shut down revenue streams making $1.2M-$1.5M annually
“This year I turned off two profit streams that I think combined were making like, 1.2 to 1.5 million a year of profit.”
Shaan Puri: Writing course generated $1M profit for 10 days of work
“I was teaching this, like, power writing course, and you know, I was only teaching it basically two to three weeks out of the years, you know, roughly 10 days on average a year, but it would generate, you know, whatever, a million bucks a year of profit.”
Shaan Puri shuts down rolling fund to invest only personal capital
“I also just announced that I'm shutting down my rolling fund. So I'll only be investing personally. Now I'm not taking any more outside money.”
Andrew Wilkinson: Raising outside fund capital creates constant cognitive interruptions
“The problem with raising money is that at the end of the day, there's people who can call you, and you owe it to answer the phone, and they can interrupt you at any given time, and especially in a rolling fund, there's like 50 of those people.”
Parr: Morning Brew sold for $75M and reached high eight-figure revenue
“I think he was 26 when he sold it at a seventy five million dollar valuation. The company now is doing high eight figures in revenue.”
Wilkinson: Andrew Huberman's Media Business Is Completely Undisruptible
“His business, I'm like, that is a completely undisruptible business unless he gets hit by a bus or something.”
Puri: TikTok Shop is an unsaturated, high-conversion arbitrage opportunity
“TikTok Shops is currently in that, like, it's very cheap, it's not that saturated, and TikTok is very motivated to promote these things, and TikTok customers are not, like, fully acclimated to the fact that now a bunch of the TikToks they see are selling produ…”