The 2023 Milly Awards: Part 2

Episode Summary

Executive Summary: This Millie Awards episode recaps the year’s most surprising people, best/worst investments, standout unsexy businesses, content picks, breakout trends, and predictions. The hosts celebrate weirdly effective operators, debate business structure and angel investing, and highlight how AI, Ozempic, and media/community-driven businesses are reshaping behavior and value creation.

Main Topics: Craziest / most delusional person of the year (Priority: 5/5): The hosts compare examples of extreme thinkers and operators, from Elon Musk to lesser-known but highly successful outliers like Val and a Turkish founder building mineral-rich food and immigration pipelines. The discussion centers on calm, logical people doing seemingly irrational things at massive scale. Best and worst investments (Priority: 5/5): Each host shares wins and failures across acquiring businesses, angel investing, crypto tax timing, and operational mistakes. A major theme is that buying existing businesses with distribution or tailwinds can outperform traditional angel investing, while bad timing and missed opportunities create large opportunity cost. Unsexy business of the year (Priority: 4/5): The group highlights boring but durable businesses such as HVAC, Pantone, and color forecasting. These examples show how obscure, standardized, or behind-the-scenes businesses can generate significant revenue and pricing power. Content of the year (Priority: 4/5): The hosts discuss standout media including The Bear season 2 episode 7, The Wager, World War II: From the Frontlines, Talk Like Churchill, Stand Like Lincoln, and books on hardship/charisma. They emphasize content that offers emotional intensity, historical perspective, or practical communication lessons. Breakout of the year (Priority: 5/5): Ozempic/GLP-1 is framed as the biggest breakout trend because it may change weight loss, cravings, and even alcohol use. Another breakout example is a podcast-clipping/player tool called Snipped, which solves podcast consumption pain points. Predictions and AI disruption (Priority: 4/5): The episode revisits prior predictions and updates new ones, especially around AI replacing assistant/admin work. The conversation suggests AI and GLP-1s are not just product trends but category-shifting forces with broad second-order effects. Live audience, community, and business leverage (Priority: 4/5): The hosts discuss their first live MFM event and how audience trust can be converted into distribution, especially when paired with a strong product. They also argue that media/influencer leverage can create outsized value in B2B and acquisition strategies.

Key Arguments: Calm, logical people can still be highly unconventional and even 'crazy' in business if they operate with extreme discipline and risk tolerance. The best investments often come from buying businesses that already work and then adding distribution, rather than only relying on venture-style startup bets. Structure matters enormously in acquisitions; clever financing and deal terms can materially improve returns. Angel investing has a poor liquidity profile for most people and can feel like gambling unless one lands a few huge winners. Opportunity cost in investing can be more important than losses from bad investments; missing a winner can be far more damaging than a small loss. Unsexy businesses like HVAC, Pantone, and color forecasting can be highly defensible because they standardize industries and have recurring demand. Ozempic/GLP-1 drugs may reshape consumer behavior at scale, potentially affecting obesity, alcohol consumption, and general craving-driven spending. AI could automate a large share of assistant and admin work in the near term because it can access calendars, email, and drives. Content about hardship and historical suffering gives perspective and makes present-day stress feel smaller. The hosts believe audience trust and distribution can act like a massive, low-cost marketing engine when paired with the right product. Managing a CEO is harder than simply hiring one; owners need to let non-fatal mistakes happen while intervening on existential risks.

Data Points: Val's first-year business profit: $10 million - A supposedly under-the-radar entrepreneur immigrated from the Soviet Union and built a business that made $10M in profit in year one. Val's business revenue: $150M-$200M annually - The same operator now owns a set of businesses generating hundreds of millions in annual revenue without raising outside money. Val's work schedule: 4am wake-up / 3pm start / 4am finish - Used as evidence of his extreme but calm operating style. Michael Dell family office starting capital: $200 million - He allegedly started a family office with a goal of making 10% returns. Letterboxd users: 10 million registered users - Andrew described buying a 60% stake in the bootstrapped film social network. Letterboxd valuation: ~$60 million - Approximate valuation at the time of purchase. Castro loss: ~$2 million lost over 5 years - Worst investment example: a podcast player that burned cash after the founders left. Angel investing capital deployed: ~$1 million - Sam said he had invested about a million dollars into angel deals since 2016. Angel investing realized returns: $0 back so far - He noted not seeing any cash returns yet despite markups on paper. Shepherd business growth: Tripled in 6-9 months - After acquiring a stake and driving audience-led customer growth, the business reportedly tripled. Value added to Shepherd: $35 million+ - The investment appreciation was attributed largely to growth after the partnership. Crypto tax-loss timing error: 35%-40% BTC rebound missed - Sam delayed repurchasing Bitcoin after tax-loss selling and missed the rebound. Whatnot valuation: $10 billion - Used as an example of a missed angel opportunity that would have been a massive winner. Shuffle volume: Millions of dollars in daily betting volume - A missed crypto casino investment opportunity described as growing very fast and profitable. House size: 8,000 square feet - Andrew's custom-built dream house was described as very large and overly customized. House loss: 30% loss - He sold the custom house after divorce and took a substantial loss. Net worth decline: About 50% on paper - Andrew said the publicly visible value of his stock-based net worth fell by half during the year. MFM live event attendance: 1,200-1,300 people - The first live show in Vancouver sold out a large theater. Hoffman Bros revenue growth: $13M in 2016 to $140M in 2023 - An HVAC business was cited as an archetypal unsexy but booming company. WGSN EBITDA: $50 million - Referenced as a related color-trend forecasting business. Ozempic / semaglutide starting discovery: June 2022 - Sean said he first heard about semaglutide around then and experimented with it. Cleaning streak: 45 straight days - Sean said he had been eating clean for 45 days and had lost around 13-14 pounds.

Pivotal Quotes: "Well, it's going to cost a little under a trillion dollars to ship 10 billion robots." — Sam: Used to illustrate the scale and craziness of ambitious robotics founders. "This business is like the can't believe it's not butter of billionaires." — Andrew: Describing Michael Dell as extremely steady, boring, and surprisingly elite. "I feel like I can rule the world. I know I could be what I want to." — Intro music / show refrain: Recurring opening/closing vibe setting the tone for the awards episode.

Implications: The episode suggests durable value is shifting toward distribution, boring but defensible businesses, and behavior-changing products like GLP-1s. For listeners, the lesson is to think more structurally, buy leverage where possible, and treat opportunity cost as seriously as direct loss.