My First Million · Episode Brief
The 2025 Milly Awards!
The annual live Milly Awards turns a year of business ideas into a verdict on what actually mattered in 2025.
The Milly Awards exist to solve a real problem with business podcasts: there's no accountability. You can predict a trend, miss entirely, and nobody goes back to check. Sam and Shaan created an annual ritual that forces exactly that reckoning — reviewing best investments, worst investments, biggest personal losses, and the year's standout guests in front of an audience, with Steph Smith as the third voice.
The best and worst investment categories are where the most credible content lives. Unlike abstract recommendations, these involve actual money with actual outcomes. The specificity of 'worst investment of the year' is the most useful segment on the pod — not because failure is more interesting than success, but because the framing forces honest analysis rather than retrospective glory-claiming.
The 'Billy of the Year' category is the show's version of calling out a narrative that dominated 2025 but probably shouldn't have. Previous years have used this slot to name the trend that consumed the most conversation relative to its actual importance — and 2025 had no shortage of candidates.
The 'Frame-Breaking Person / Favorite Guest' segment at nearly an hour is the longest in the episode, which tells you something about where the real energy is. Sam and Shaan's guests tend to be the best signal for what they're actually paying attention to, and the conversation about who changed how they think is more revealing than any award category.
Steph Smith's presence gives the episode a structural anchor it wouldn't have with just two people who agree on most things — she's willing to defend a different verdict.
Key Ideas
- →The worst investment of the year segment is the most valuable because it forces specific, accountable analysis rather than curated retrospectives.
- →Sam and Shaan's 'Billy of the Year' award names the trend that consumed the most cultural bandwidth in 2025 relative to its actual signal value — a useful frame for filtering media noise.
- →Steph Smith's role as third voice changes the dynamic from mutual affirmation to actual debate in a way that produces better verdicts.
- →The favorite guest segment is functionally a ranking of the year's most generative conversations — more useful than any best-of episode list.
- →The Milly Awards structure creates yearly accountability for predictions made throughout the year, which is unusual for a show in this format.
Worth Remembering
The specific worst investment reveal — actual money lost publicly is rarer and more credible than anything hypothetical.
The 'Billy of the Year' naming — the category exists to call out what the tech and business media collectively got wrong about 2025.
The 'Coolest Moment of the Year' segment, which tends to surface the event that best captures where culture and business actually intersected.
Steph Smith defending a verdict Sam and Shaan don't share — the disagreement is brief but unusually direct for a show that rarely shows interpersonal friction.