Dec 30, 2024 · 1h 12m · my-first-million
The 2024 Milly Awards
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In the fourth annual 'Milly Awards,' co-hosts Sean Puri and Sam Parr review their year across eleven custom categories, analyzing major financial investments, personal blunders, productivity frameworks, inspiring figures, and key lifestyle goals for the year ahead.
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 99.8% of the talking time here. How this is scored →
The hosts as informed peer 6.5 Guest teaching 2.1 Guest disagreement 1.6 The hosts pushing back 1.7
speaking balance: gold is the hosts, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:02:06 Shaan attacks the two-hour commute plan
Shaan directly attacks Sam's plan to commute two hours a day to New York, calling it self-harm and a horrible decision backed by unhappiness statistics.
Hardest push from the hosts ▶ 1:02:20 Refusing Sam's premise on office commutingShaan rejects Sam's assumption that getting an in-person office requires long travel, illustrating his own model of moving teammates within 10 minutes.
Biggest teaching moment ▶ 52:00 Mohnish Pabrai's investing formula explainedShaan relays Mohnish Pabrai's Seinfeld analogy about waiting, showing how great investing requires comfort with extreme boredom rather than constant action.
The host holds their own ▶ 6:00 Shaan details the inverse All-In trade returnsShaan backs up his counter-consensus thesis with concrete numbers, detailing 500% gains on Meta and massive Google returns by taking the other side of public tech commentary.
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 |
|---|---|---|---|---|---|---|
| Best Investments: Tipping, Passive Real Estate, and Inverse Trading | 7 | 2 | 2 | 2 | Shaan breaks down his specific investment philosophy, detailing his passive real estate returns and his systematic inverse trading strategy against the All-In podcast with exact ticker examples. | |
| Worst Investments: The Pitfalls of Active Real Estate Ownership | 6 | 1 | 1 | 1 | Sam openly reflects on hubris in real estate and the operational burdens of ranch ownership, while Shaan outlines his threshold rule for active versus passive yield. | |
| Sponsor Spotlight: HubSpot's 200 AI Business Ideas | 6 | 2 | 2 | 2 | After the sponsor read, Shaan analyses personal psychological pitfalls in market timing during COVID and crypto drawdowns, sharing his mistake picking Unity over Nvidia. | |
| Biggest Personal Loss: Time Mismanagement and Holiday Madness | 5 | 1 | 3 | 2 | Both hosts exchange personal stories about post-baby time management struggles and holiday chaos like Elf on the Shelf, gently disputing each other's definitions of productivity. | |
| Coolest Moment: Private Jet Journeys and Family Mountain Getaways | 5 | 1 | 1 | 1 | Sam recounts a private jet trip with a famous mentor while Shaan shares hosting a catered family Thanksgiving in Tahoe, both agreeing that shared experiences make the best moments. | |
| Best Life Hacks: Analog Weekly Planning and the Highs & Lows Channel | 7 | 2 | 1 | 1 | Sam shares his analog weekly executive briefing method, and Shaan introduces his Slack 'highs and lows' channel system designed for emotional regulation and stoic equilibrium. | |
| Billy of the Year: The Transformations of Mark Zuckerberg and Scott Heiferman | 7 | 3 | 1 | 1 | Shaan presents a detailed case for Mark Zuckerberg's total life and strategic turnaround in open-source AI and fitness, while Sam highlights Meetup founder Scott Heiferman working frontline jobs. | |
| Frame Breaking Person: Bryan Johnson and the Zestful Life of Nick Gray | 7 | 3 | 1 | 1 | Sam discusses Bryan Johnson's 500-year historical legacy framework, and Shaan delivers an extensive breakdown of Nick Gray's unconventional life experiments and Cloudflare fanaticism. | |
| Favorite Podcast Guests: Amjad Masad, Mohnish Pabrai, and Mike Posner | 8 | 4 | 1 | 1 | Shaan and Sam review insights from top interviews of the year, comparing Mohnish Pabrai's patience-driven value investing with Mike Posner's philosophy on avoiding the hit-chasing trap. | |
| Best Product of the Year: ChatGPT Advancements and 'The Brick' | 6 | 2 | 1 | 1 | Shaan selects ChatGPT as a workflow amplifier, while Sam demonstrates 'The Brick' hardware device to enforce focus, sparking discussion on forced friction and habit training. | |
| Upcoming Changes: In-Person Workspaces and Creative Gyms | 7 | 2 | 4 | 6 | Shaan aggressively challenges Sam's plan to commute two hours to an office, countering with his own setup of relocating an employee nearby, before exploring creative gym habits. |
Statements from this episode (16)
Shaan Puri: Brother-in-law's real estate yields 30% to 40% passive returns
“I just started giving him money and it's been amazing. I don't lift a finger and I'm getting like, you know, 30, 40% returns with all the tax advantages. So that was my best investment and I'll be doubling down there.”
Shaan Puri made 500% buying Facebook against Chamath Palihapitiya's short thesis
“Chamath tweets out the growing short case against Facebook, and he says, regulation is a problem, tax is a problem, antitrust is a problem, all this stuff. I bet on Facebook I'm up five X, so I made 500% on that trade, and so basically they went anti-Bitcoin f…”
Sam Parr: Brooklyn real estate investment yielded a 28% annual return
“Him and I, he was the main guy. I was a very small investor. We bought a building in Brooklyn. I killed it on that. I think I had a 28% annual, like, return, not including the tax stuff.”
Sam Parr: Actively managed real estate functions like a demanding small business
“Buying real estate that you have to operate. It's just like starting a small business that you have to work 10 hours a week on. It sucks. It's hard.”
Shaan Puri requires a 50% hurdle rate for any active investment
“My rule is if it's active, it has to generate more than 50%. The bar is way different. If it's passive, it could be seven percent. It's fine. But if it's active, it's gotta be more than 50%. If it's active investment.”
Sam Parr sold 100% of his portfolio at the COVID market bottom
“Literally, the day it was its lowest, I sold 100% of everything I owned.”
Shaan Puri heavily backed Unity instead of Nvidia for AI and lost
“And I plowed a bunch of money into Unity instead of NVIDIA. I was looking at the two and I was like, is it Unity or NVIDIA? And I should have just bet on both, but instead I picked Unity and Unity has done nothing and NVIDIA became the most valuable company in…”
Sam Parr: New parents must pretend work matters to maintain productivity
“When you have a kid, and I experienced this, where I'm like, oh, nothing else matters. But you should still kind of pretend it does so you could, like, kind of be productive, and I kind of, like, acted like nothing else mattered.”
Sam Parr: Paying for entire family vacations is consistently among life's best experiences
“Taking family and just paying for it, and it sounds like a ridiculous, and it's very expensive, and it's very challenging for a lot of people, but if you can pull it off, it is almost always one of the best moments.”
Shaan Puri: Logging business highs and lows in Slack regulates founder psychology
“I have a slack channel for every company. I have a slack channel called highs and lows and in it, anytime there's a high, high in the moment of that business or a low, low... Instead of addressing the current problem, or basking in the glory of the current hig…”
Shaan Puri: Mexican textile import ban paralyzed his e-commerce warehouse
“On Christmas Eve, the Mexican government decided to ban all imports into Mexico of textiles, which effectively shut down my entire warehouse on Christmas Eve. And we can no longer like operate because our warehouse is in Mexico.”
Sam Parr: Meetup.com founder Scott Heiferman now works in an Amazon warehouse
“And as of late, if you go to his LinkedIn, he has not made an ordeal out of this. This is all other people like us talking about it, making an ordeal out of it. But now he's an Amazon warehouse worker and he's working in the Amazon warehouse and he kind of is …”
Shaan Puri: Nick Gray sold his renegade museum tour business for millions
“He loved museums so he created a business about renegade the museum tours where he would take you on his own tour because museums were boring and he's not boring and he would take you on his own tour unofficially not a part of the museum ended up selling that …”
Shaan Puri: Mohnish Pabrai was the podcast's first episode hitting 1M views
“It's at two and a half million on YouTube alone. So it was the first, first, first podcast episode. We're doing this for four or five years now. First podcast episode that crossed like a million on, on YouTube.”
Puri: Creators succeed by making what they find cool rather than chasing hits
“I'm just gonna make what's cool to me, and sometimes, the whole world will agree. And I just thought that was such a dope philosophy as a creator to take, which is, I'm just gonna make what's dope for me, and then once in a while, the whole world will agree wi…”
Sam Parr uses 'The Brick' daily until noon to block phone distractions
“Every morning when I'm getting ready to go to the gym, I walk by my door and I brick my phone, which means it's completely unusable other than making phone calls. So my wife can call me for an emergency Spotify and my workout app. And so I will keep it like th…”