Dec 31, 2021 · 1h 47m · my-first-million
The Milly Awards 2021
0:00 / 0:00
▶ Watch on YouTube →
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In the 2021 edition of the Milly Awards, hosts Sean Puri, Sam Parr, and Andrew Wilkinson compete across business, investment, and lifestyle categories to celebrate the standout entrepreneurs, biggest lessons, and future trends of the year.
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 69.9% of the talking time here. How this is scored →
The hosts as informed peer 5.6 Guest teaching 2.8 Guest disagreement 1.6 The hosts pushing back 1.8
speaking balance: gold is the hosts, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:37:45 Andrew dismisses image NFTs as digital Beanie Babies
Andrew strongly pushes back against NFT mania, asserting that protocols are temporary and current digital image NFTs lack enduring underlying value.
Hardest push from the hosts ▶ 1:45:15 Andrew rejects Sam's claim that he launched a SPACAndrew firmly clarifies Bloomberg's incorrect reporting, explaining the difference between an expensive SPAC promotion and a low-dilution reverse takeover.
Biggest teaching moment ▶ 29:33 Andrew explains closed-end fund NAV discountsAndrew breaks down Bill Ackman's public holding structure, educating the hosts on how Amsterdam-listed vehicles provide downside cushion by trading below asset value.
The host holds their own ▶ 36:20 Shaan and Sam calculate missed angel upside in DeelShaan details Andreessen's early markup on Deel while Sam calculates the exact dollar loss resulting from delayed angel follow-ups.
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 |
|---|---|---|---|---|---|---|
| Establishing the 2021 Milly Awards Format | 6 | 3 | 1 | 1 | The hosts establish the awards format and debate their 'Billy of the Year' picks. Shaan demonstrates domain knowledge detailing Elon Musk's incentive structure and Vitalik Buterin's token burn mechanics. | |
| Category 2: Breakout Company of 2021 | 6 | 2 | 2 | 2 | The trio compares OpenSea, Pieter Levels' solo business empire, and MicroAcquire. Andrew and the hosts exchange perspectives on micro-SaaS economics and Twitter branding strategies. | |
| Category 3: Best Unsexy or Simple Business | 5 | 3 | 1 | 1 | The discussion covers unsexy cash-flow businesses including fake private jet photo studios, parking lot line striping, and OnlyFans web traffic stats. | |
| Category 4: Best Investment of 2021 | 6 | 4 | 1 | 2 | Andrew details why he heavily invested in Pershing Square Holdings at a discount to NAV, while Shaan and Sam dissect the explosive valuation trajectory of Deel. | |
| Category 5: Worst Investment of 2021 | 5 | 3 | 2 | 2 | The group analyzes bad investments in Zillow, small unmanaged startups ('embers'), and post-COVID tech selloffs, exploring prediction markets as an alternative. | |
| Category 6: Best Products and Tools of 2021 | 5 | 3 | 2 | 3 | The hosts and guest trade recommendations on digital and physical tools, with playful teasing about hiring private chefs and casual indoor clothing. | |
| Category 7: Personal Learnings and Relationship Hacks | 5 | 2 | 1 | 1 | Shaan and Andrew have a vulnerable, candid conversation about the pitfalls of sending curt one-line text replies and managing friendships as public figures. | |
| Category 8: Books of the Year and Media Subscriptions | 6 | 3 | 2 | 2 | Andrew discusses media titans Murdoch and Turner, prompting Shaan to share firsthand observations of Murdoch's work ethic and an analysis of the All-In podcast dynamic. | |
| Category 9: MFM Guest and Person of the Year | 6 | 2 | 2 | 2 | The hosts reflect on favorite podcast guests like Hasan Minhaj and Steph Smith, and Andrew highlights the fast turnaround acquisition of Buyer by Ramp. |
Statements from this episode (26)
Wilkinson: Mark Anthony Group did $4B revenue in 2020 with zero debt
“And now they do 1.4 or sorry, four billion dollars of revenue last year in 20, 20. And the craziest thing about this guy is he owns, I believe a hundred percent of the business and he has no debt because he had been almost in bankruptcy multiple times.”
Vitalik Buterin donated $1B in SHIB and burned remaining $5B
“And what he did was he donated a billion dollars of it immediately to India. And then he dumped the other five billion and just burned it and just said you know, so, so that like it would, so that the price, if he sold it all on the open market, it would it wo…”
Sam Bankman-Fried is crypto's wealthiest known billionaire at $20B
“The Sam Bankman Freed guy, he's currently the wealthiest person from crypto wealthiest known person from crypto. So, you know, nobody knows who Satoshi is, but Sam Bankberfried is the next one. He's got like 15 or twenty billion dollar net worth from crypto, i…”
Puri: OpenSea grew GMV from $24M in 2020 to $15B in 2021
“In 2020, so last year, they did twenty four million dollars in GMV. Pretty small overall. ... This year, fifteen billion. So going from twenty four million to fifteen billion in one year, that's 650 X.”
Parr: Pieter Levels reached nearly $5M in revenue in 2021
“For the longest time, only like three, four, 500,000 dollars a year in revenue. Like neat, but not that cool. This year, he got close to five million in revenue. And for a one person internet business, that's pretty phenomenal.”
Hiring employees creates an operational beast that restricts founder freedom
“Once you start, once you get an office, once you have employees, you have this beast to feed. Whereas Peter could just check out.”
Puri: American Striping grew from $400K to nearly $15M in three years
“And so she has this company, American Striping. I think it started about three years ago. And you know, 400,000 dollars the first year, seven million the second year, fifteen million almost the third year, and just crushing it”
Puri: Crocs stock rose 13x in one year following March 2020
“Dude, when the pandemic happened, so March, you could have bought a pair of Crocs for, I don't know how much Crocs go for, let's call it a hundred bucks. Maybe there's a little less. You could buy a pair of Crocs and you could buy the stock for 10 dollars a sh…”
Puri: OnlyFans receives 250 million monthly visitors
“It's two hundred fifty million. You're off by 10 X, an order of magnitude. Is it really? That was going to be my other unsexy business was actually the business of sexy which was like, I had no idea they get two hundred fifty million visitors per month.”
Andrew Wilkinson holds 95% of his net worth in Tiny
“So I have about 95% of my net worth in tiny. And our kind of core businesses.”
Wilkinson: Pershing Square Holdings trades at a ~30% discount to NAV
“And as I dug into it, I realized that it perpetually trades at a discount to the net assets there. So if there's a hundred dollars worth of stocks, it trades at about 70 dollars, meaning that the market could go down 30% before you've lost any money in the por…”
Wilkinson: Ackman turned $25M into $2.7B on 2020 COVID trade
“Like he last year, he turned twenty five million dollars into 2.7 billion. And I got to ride along with him on that.”
Deel grew ARR from $4M to $50M in one year
“It, that it was valued this year at five and a half billion. Like, you know, two years later, they said he, and the founder tweeted this out so I can share this. They ramped up revenue from four million to fifty million in ARR in one year. And they went from 5…”
Shaan Puri lost 56% on his $100K Zillow stock investment
“It's down 56%. So I bought a hundred K and now my hundred K is 44 K left.”
Clubhouse will fail to reach Twitter or Facebook scale
“Andreessen put in a four billion dollar price tag on it, basically betting that it's gonna become like a Twitter, it's gonna become a Facebook or a Snap, and it's not happening. That has, that hasn't happened.”
Hiring a private chef yields the highest return on life quality
“It is the biggest life quality change because you get your time back. Plus you eat healthier. Plus it's actually tasty. Cause you probably aren't a great cook.”
Wealthy individuals consistently state they need double their current net worth
“The New Yorker did an, did a study where they like, Asked a bunch of wealthy people and like, it doesn't matter if the person had 1,100,000 or fifty million. They always said they'd be more comfortable if they had two X.”
Saying 'I am busy' means you are poor
“Cause basically to me, when the phrase I'm busy means I'm poor, it's like, if I think wealth is freedom of time and to be able to spend it how you want, then saying I don't have time means I'm poor.”
Wilkinson: Facebook Acqui-Hires Potential Competitors Solely to Shut Them Down
“Facebook basically just buys companies to shut them down. Right. They find promising social networks that might compete with them. They go buy them for tens of millions of dollars before they turn into anything. And they bought his company and it's kind of lik…”
David Sacks is overly political and driven by confirmation bias
“David Sachs is super smart, but then, like, super fucking political, and to an annoying extent, and is always just looking for some story that, like, supports his point of view and usually that point of view is that everybody else is biased, but like, you know…”
Buyer launched for under $100K and sold to Ramp within a year
“So we start this business called buyer. We go 50, 50 on it. I promote it and talk about it, given the rails and accounting and stuff. And we literally, I think we started it for like 50 or a hundred grand and we sold it to ramp about maybe six months ago now f…”
YouTuber Meet Kevin generates $30M annually with just four employees
“And now his business is making thirty million dollars a year with four employees.”
Tech salary inflation will reverse as remote hiring shifts overseas
“I think that this high salary inflation is not here to stay. I think what's happened is all these companies down in San Francisco are going, oh, crazy. We can hire cheap people in Canada, but they're not yet going, oh, hey, we can hire people in India and the …”
Current NFT protocols are temporary and won't exist in five years
“But I just think right now it's all half baked and all the Protocols are all made up and won't exist in five years.”