Dec 29, 2022 · 1h 55m · my-first-million
The 2022 Milly Awards (#401)
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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 third annual Milly Awards, hosts Sean Puri, Sam Parr, and guest Andrew Wilkinson review the key business moves, investments, and cultural moments of 2022 while setting wild predictions and personal goals for 2023.
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 70.9% of the talking time here. How this is scored →
The hosts as informed peer 5.6 Guest teaching 3.6 Guest disagreement 2.5 The hosts pushing back 2.6
speaking balance: gold is the hosts, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:23:03 Andrew condemns platforming fraudsters
Andrew aggressively challenges the hosts' editorial judgment, arguing that giving platform exposure to figures like Billy McFarland or Tai Lopez unethical legitimizes psychopaths.
Hardest push from the hosts ▶ 1:18:37 Hosts challenge Andrew over Bill AckmanSam and Shaan refuse Andrew's moral standard on media platforming by grilling him on public controversies surrounding his business partner Bill Ackman.
Biggest teaching moment ▶ 22:16 Andrew's granary rats mental modelAndrew reframes Shaan and Sam's inclination to fight petty legal battles by citing Munger's granary rats metaphor, illustrating why successful entrepreneurs must absorb inevitable friction costs.
The host holds their own ▶ 27:48 Shaan proves Sam Altman's track recordShaan counters Sam's dismissal of OpenAI's breakout status by quoting Paul Graham's 2009 analysis predicting Altman's unstoppable trajectory.
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 |
|---|---|---|---|---|---|---|
| The 2022 Milly Awards: Introductions, Banter, and Annual Metrics | 4 | 1 | 1 | 1 | The hosts and guest open with lighthearted apparel banter and review the podcast's annual performance metrics. The tone is thoroughly collaborative and celebratory. | |
| Billy of the Year: Zuckerberg, Brett Adcock, and Palmer Luckey | 5 | 3 | 2 | 2 | Participants share their top entrepreneurial figures of 2022, including Palmer Luckey, Brett Adcock, and Syed Balkhi. Andrew highlights Luckey's willingness to speak unfiltered without corporate PR handlers. | |
| Biggest L of the Year: Procrastination, Time Selling, and Landlords | 6 | 5 | 3 | 3 | The group breaks down their biggest personal and financial losses, from Andrew's debt hedging delay to Shaan's legal battle with a landlord. Andrew introduces stoic principles and Charlie Munger's 'rats in the granary' framing to explain why small disputes should be abandoned. | |
| Breakout of the Year: OpenAI, Liver King, and Sam Altman | 6 | 4 | 5 | 5 | Sam forcefully rejects Andrew's selection of OpenAI as a breakout company, arguing it merely met expectations and touting viral figures like Liver King instead. Shaan counters by breaking down Paul Graham's 2009 essay predicting Sam Altman's trajectory. | |
| Favorite Unsexy Business: Aunt Flow, Restroom Disruption, and Hustlers University | 6 | 4 | 2 | 2 | The hosts and guest discuss lucrative unsexy business models, including restroom product dispensers, hotel supply management, and Andrew Tate's membership funnel. The discussion focuses on business economics and high-margin recurring cash flows. | |
| Best Investment of 2022: Triple Whale, Girlboss, and Podcast Growth | 6 | 5 | 2 | 2 | Each participant shares top investments of the year, with Andrew detailing his turnaround of distressed asset Girlboss into a cash-flow generator. Shaan outlines Triple Whale's valuation growth and the compounding value of hosting private retreats. | |
| Worst Investment of 2022: Real Estate, Crypto Crash, and Venture | 6 | 4 | 3 | 3 | The conversation shifts to bad asset allocations, including crypto collapses, direct real estate headaches, and illiquid venture stakes. Andrew contrasts the psychological freedom of cash-flowing EBITDA businesses against speculative venture equity. | |
| HubSpot Sponsor Break: Centralized CRM Platform for Growing Teams | 5 | 3 | 1 | 2 | After an ad break, the hosts and guest exchange recommendations for top books, creators, and podcasts of the year, reviewing biographies and educational financial accounts. | |
| Wild Predictions for 2023: AI Expansion, Musk Scrutiny, and Goals | 5 | 3 | 2 | 3 | The panel grades past forecasts and provides wild predictions for 2023 regarding AI platform competition, regulatory scrutiny, and personal fitness milestones. | |
| Coolest Moment of 2022: Scientific Philanthropy and MrBeast Half-Court Bet | 5 | 2 | 2 | 2 | Highlights of 2022 are recounted, including Andrew's scientific research matching grant with Andrew Huberman and Shaan's half-court basketball wager with MrBeast. | |
| Delusional Personalities: Platforming Controversial Figures and Longevity Biohackers | 6 | 6 | 7 | 6 | Andrew vigorously criticizes the hosts for giving airtime to controversial figures and convicted fraudsters like Billy McFarland. Sam and Shaan push back by emphasizing journalistic neutrality and questioning Andrew's defense of his own high-profile business partners. | |
| Top Relationship Hacks: Cold Plunges, Hosting Events, and Sparring | 5 | 4 | 2 | 2 | The group shares personal life optimizations, comparing sauna/cold plunge routines, hosting large-scale events, and using morning physical sparring to reduce stress. | |
| Best Tools Under $1,000: Clay CRM, MyBodyTutor, and Automated Accounting | 7 | 3 | 1 | 2 | Participants review high-utility tools and services under $1,000, with Shaan giving an in-depth breakdown of automated bookkeeping and proactive tax strategy software. | |
| Key Business Adjustments for 2023: Delegating, Calmer Leadership, and Patience | 6 | 3 | 2 | 2 | The episode concludes with structural changes for 2023, covering executive delegation, calm leadership, and patience in selecting long-term business projects. |
Statements from this episode (25)
Puri: My First Million hit 20M downloads in 2022
“Twenty million downloads this year for the podcast, which is I think six times bigger than last year by maybe four or five, five times. I might have my math wrong there, but I think YouTube's up six X and the pod is up four X or something like that.”
Sam Parr: Brett Adcock put ~$200M of personal capital into humanoid robotics
“He made a lot of money when he sold his company called Vetteri for a hundred million dollars. Then he created, Vetteri is like a recruiting company. It's not sexy. But then he created a flying drone company that he took public called Archer. It was worth two o…”
Wilkinson: Procrastinating on debt hedge documents cost $500,000
“And so these documents were sitting in our office and I was like,
oh, I'll do it tomorrow.
I'll do it tomorrow.
I kept putting it off.
And then finally I signed it.
And I realized that between the time that I, it was sitting there for a week and in that week, …”
Sam Parr estimates ConvertKit founder Nathan Berry is worth over $200M
“Like Nathan Berry Nathan Berry owns ConvertKit. He's probably worth 200 plus million dollars based off the valuation of ConvertKit.”
Wilkinson: Large businesses must accept minor nuisance losses
“If you own a granary, you have a big warehouse full of grain, There's gonna be rats. You can keep killing them over and over again, but they're gonna always come back, and it's better to just accept that there's rats out there.”
Puri: Sam Altman was Airbnb's first seed investor
“He then invested in Airbnb right away and was the first seed investor in Airbnb.”
Puri: Aunt Flow reached high seven-figure run rate and supplies Apple stores
“And so they're at like, you know, they're definitely, you know, sort of like high seven figures run rate where they have all these great contracts and they have, you know, they're the official dispenser for all the Apple stores and for like, you know, the whol…”
Parr: Andrew Tate's Discord community brings in over $100M in revenue
“It's, like, tens of thousands of members. Yeah. No, no, no, no, no, no. Like, a million members. Oh, wow. Like, we're talking nine figures in revenue, and CoffeeZilla, like, did it. He's like, look, here's all the members. If you multiply that by 50, and then …”
Shaan Puri turned a $75,000 investment in Triple Whale into $3.3M
“I think our 75,000 dollar investment in triple whale is currently worth 3.3 million. And so that's been the biggest breakout from the fund so far.”
Wilkinson: Distressed acquisition Girlboss generates its purchase price in annual profit
“Basically now the business is, I won't say numbers, but it's making as much as we paid for it every year in profit. And I think it's probably five or 10 X more valuable than what we paid for it at least.”
Sam Parr regrets buying real estate instead of investing in funds
“I regret buying real estate. I wish I didn't own any real estate, and I wish I just invested in other people's funds.”
Shaan Puri lost 100% of his investment in crypto token Luna
“People know my portfolio is essentially tech stocks and crypto. Tech stocks down somewhere between 40 and 85% this year. Crypto down 75% this year, or sometimes a hundred percent in certain cases. I think Luna has to be my pick because it went to zero.”
Wilkinson: Buying Cash-Flowing Businesses Beats Venture Capital
“I think that I'm much better off incubating businesses and buying businesses. Cause it's a very steady, 15 to 30% cash return. And I feel it. I feel the wind in a much bigger way.”
Sam Parr: Elon Musk will face severe cancellation and Tesla will tank
“One, Elon Musk either dies or he or he gets canceled or he gets canceled in an incredibly like serious way. And Tesla stock completely tanks.”
Sam Parr: OpenAI will face government regulation in 2023
“The second thing is so open, I open AI. Something involving regulation is going to happen.”
Wilkinson: Major AI competitors to GPT-3 will emerge within six months
“There's going to be a lot of. A lot of other players in that space coming out over the next probably three to six months. And that it will be, there's going to be an ecosystem of offering similar to AWS and Azure and Google cloud. I think it'll be the same thi…”
Puri: MrBeast failed to pay out a $10,000 half-court shot bet
“It's also actually my biggest L of the year because he didn't pay me. And then I had to follow up. And I followed up two times, three times, and now I'm basically begging for the money.”
Wilkinson: Ackman exited his short position before his viral CNBC interview
“If you actually look at the timeline, he'd already sold out of that position when he went on CNBC.”
Puri: Hosting events takes 5x the work but yields 500x the payoff
“The first is a principle that I've had for a long time. It's called don't attend the party, host the party. This is my I have a rule. I don't attend other people's events typically, unless it's a real good friend who really wants me to, but I will host. So I t…”
Andrew Wilkinson: Khan Academy has an amazing 1-hour financial statements course
“If you want to learn Khan Academy has an amazing introductory course takes about an hour and you'll learn everything you need to know.”
Shaan Puri: There will be a massive surge in IRS tax audits
“I think they hired 80,000 87,000 new hires. And so I think there's gonna be a shitload of audits, which is why I wanted to be like super buttoned up with everything.”
Sam Parr hired a CEO from day one for his new venture
“For, I have a new thing that I'll launch that it's live, but I'll announce it later. I'm hiring a CEO for it. I've already like done that and I've never done that early on.”
Shaan Puri sold Milk Road because he lacked a three-year commitment
“Same thing with the milk road. Part of the reason I sold it was I was like, I don't think this was the project that I want to work on every year. You know, for the next three years. And so if I don't want to work on it for the next three years, I should just s…”