My First Million · Episode Brief
Giving founders brutally honest feedback
Sam and Shaan are most useful when they're giving harsh feedback nobody asked for — and this episode is 20 minutes of that before it turns into something stranger.
The episode opens with what the title promises: Sam and Shaan cataloging the business traps they see founders fall into most consistently. This isn't abstract. The traps they identify are specific — building for press instead of customers, optimizing for a fundraise instead of a business, mistaking activity for progress — and the discussion has the texture of people who have watched the same mistakes play out enough times to be genuinely impatient about it.
What makes the second half more interesting is the turn toward old-school businesses making unexpected comebacks. The Onion's decision to revive its print edition is treated not as nostalgia but as a signal — that there are audiences willing to pay for physical objects when those objects carry a status signal that digital content can't replicate. Oberweis Dairy's milk delivery model gets the same treatment: a 100-year-old distribution mechanic that turns out to work better than anyone would have predicted in a world where people are nostalgic for service and local provenance.
Joe Lemandt and Alpha School represent the most ambitious idea in the episode. Alpha uses a mastery-based learning approach where students spend part of their day on self-paced academics and the rest of the day on entrepreneurial projects. The hosts debate whether this is a genuine educational innovation or a niche product for a specific type of family — and they don't fully resolve it, which is the right call.
Grind Academy, a homeschooling facility for kids whose parents want them training harder and learning more independently, closes out the episode with a question that MFM returns to often but rarely answers: what does education look like if you design it from first principles rather than backward from existing institutions?
Key Ideas
- →Shaan's core 'business trap' diagnosis was that most struggling founders are solving for the wrong scorecard — optimizing for metrics that impress investors rather than metrics that indicate a healthy business.
- →Sam argued that The Onion's print revival is a case study in what happens when irony becomes a product category — people who buy a print Onion aren't reading it, they're displaying it.
- →Oberweis Dairy demonstrates that subscription-plus-delivery is not a new business model invented by DTC startups — it predates the internet by a century and the operational complexity is largely solved.
- →Alpha School's model — two hours of academics, the rest of the day on real projects — inverts the traditional school schedule and implicitly argues that most classroom time is wasted.
- →The Grind Academy discussion surfaced the hypothesis that the market for rigorous, non-coddling education is larger than mainstream schools acknowledge — and that parents willing to pay for it are a real and underserved buyer.
Worth Remembering
Shaan's list of 'business traps' included one that hit awkwardly: spending more time on the podcast about business than on actual business — and both hosts laughed uncomfortably.
Sam's genuine surprise that Oberweis is profitable and growing despite being a business model that sounds like it should have died in 1980.
The moment where the Alpha School conversation shifted from 'interesting education model' to 'wait, is this what Shaan is going to do with his own kids?' and Shaan got visibly thoughtful.
The Grind Academy founder story — building a homeschooling co-op designed around physical training and independent work — described as the thing Shaan would build if he were a parent in 2025.