The 2021 Milly Awards

Episode Summary

Executive Summary: This year-end episode is a Millie Awards style recap where the hosts debate the best businesses, investments, tools, books, guests, and predictions of 2021. Themes include the appeal of simple businesses, the power of compounding and good timing, skepticism toward hype cycles like SPACs and NFTs, and a recurring ethos of “bet on yourself.”

Main Topics: Millie Awards format and year-end tradition (Priority: 5/5): The episode revives the annual Millie Awards, where the hosts independently pick winners across categories and react in real time. The format is part awards show, part business brainstorming session, and part personal reflection. Breakout companies and businesses (Priority: 5/5): The hosts debate standout breakout companies such as OpenSea and MicroAcquire, plus one-person businesses like Peter Levels’ portfolio. The discussion emphasizes creation of new markets and the rise of profitable, bootstrapped internet businesses. Best and worst investments (Priority: 5/5): The hosts compare successful bets like Pershing Square Holdings and real estate to bad calls like Zillow and holding COVID winners too long. The segment highlights valuation discipline, timing, and the pain of missed follow-through. Favorite tools and products (Priority: 4/5): They share practical favorites under and over various price points, including apps like Truebill, consumerlab, and OtherShip, plus physical tools like a silk pillowcase, a lockbox, and a chef. The focus is on improving daily life and lowering friction. Relationship and self-improvement lessons (Priority: 4/5): The conversation turns reflective as the hosts discuss communication habits, marriage routines, and personal flaws like being too blunt or too distant. Several hacks are shared, including weekly meetings, card games, and learning to stay quiet. Books, podcasts, and people worth following (Priority: 4/5): The hosts recommend books like 'Clash of the Titans,' 'Endurance,' and 'Think on These Things,' and podcasts like All-In and How to Take Over the World. They also spotlight people such as Dharmesh Shah, Hassan Minhaj, and Nikita Bier. Predictions and trend skepticism (Priority: 5/5): They debate what is overrated or likely to change, including SPACs, NFTs, and creator-economy hype, while making forward-looking bets on VR, stablecoins, and remote/globalized hiring. The tone is optimistic but skeptical of overhyped narratives.

Key Arguments: Simple, unsexy businesses can generate extraordinary returns if they solve a mundane problem well, as shown by vending machines, striping, and fake private-jet sets. Bootstrapped or founder-owned businesses can be more compelling than VC-backed hype because they often preserve control, margins, and lifestyle flexibility. Timing matters enormously in investing; a great company bought at the wrong valuation or with bad follow-through can still be a major miss. Many 2021 market darlings were driven by narrative rather than fundamentals, making SPACs, NFTs, and some COVID winners vulnerable to reversal. Relationship quality improves when people communicate intentionally through structured check-ins, better listening, and fewer reactive one-liners. The best content and podcasts come from guests who actually know the show and can engage naturally, rather than just perform a promotional interview. Remote work and global labor markets will continue pushing talent and work opportunities beyond North America, which could compress inflated salary expectations over time.

Data Points: OpenSea gross merchandise value growth: $24 million to $15 billion - Andrew cites OpenSea’s jump from 2020 to 2021 as evidence of breakout-company scale. OpenSea growth multiple: ~650x - Derived from the $24 million to $15 billion GMV surge. Pieter Levels revenue: ~$5 million - Sam says the one-person internet business grew from a few hundred thousand annually to nearly $5M. Vending machine business revenue: $30,000/month - Sean’s example of a simple business doing strong recurring revenue. Vending machine business profit margin: ~50% - Half of the monthly revenue is described as profit. Fake private-jet set rental rate: $70/hour - Andrew describes an influencer studio that rents a private-jet interior set. Fake private-jet business monthly revenue: $20,000–$40,000/month - Estimated based on the rental rate and usage. American Striping growth: $400K year 1, $7M year 2, nearly $15M year 3 - Sean highlights the striping company’s rapid expansion. American Striping margin: 60%–70% profit - Cody Sanchez’s example of a high-margin boring business. OnlyFans monthly visitors: 250 million/month - Sean cites this as a surprising scale benchmark for the adult-subscription economy. Average visit duration on OnlyFans: 4 minutes - Sean mentions the average session length. Pershing Square Holdings discount: ~30% discount to net assets - Andrew explains why he likes the vehicle as a defensive way to own blue-chip assets. Bill Ackman trade performance: $25 million to $2.7 billion - Andrew points to Ackman’s COVID-era trade inside Pershing Square Holdings. Austin lot project profit: ~$500,000 tax-free profit - Sean describes his real-estate development project as a favorite active investment. Deal investment outcome: $25,000 at ~$1M valuation potential to $11M+ paper value - Sean explains missing the initial round, then investing at a much lower valuation before the company later reached $5.5B. Company revenue growth example: $4M to $50M ARR - Sean says the startup’s ARR surged in one year after his investment. Company headcount growth example: 50 to 550 employees - Sean cites the startup’s rapid team expansion. Zillow stock decline: -56% - Sean says his Zillow position lost more than half its value. Crocs stock performance: 13x in one year - Sean cites Crocs as a pandemic-era winner tied to Post Malone and charm accessories. Oculus sales: 10 million units - Used to argue that VR is not dead and may still be early. PlayStation sales: 14 million units - Mentioned for comparison to Oculus sales. SPAC trend growth: $80B in 2020 to $160B in 2021 - Sean uses this to argue the SPAC boom is overheated. Chamath SPAC performance: ~ -30% YTD - Sean cites the poor average performance of his SPACs as a reason to be skeptical.

Pivotal Quotes: "If we could put in pill form all the benefits that exercise gives you, it would be the most successful medicine of all time." — Andrew: Early discussion about exercise, sleep, and the book The Body. "Dude, that's crazy. That mistake, that's a $10 million mistake." — Sean: Sean reacts to missing an early investment round in a fast-growing startup. "Shut the fuck up." — Sean: Sean summarizes his relationship lesson about not over-talking or over-stirring issues.

Implications: Listeners come away with a bias toward practical, high-margin businesses, disciplined investing, and intentional relationships. The episode suggests future winners may come from boring execution, not hype.