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The strategies and decisions behind how startups grow, stumble, and win. Every Monday and Thursday.

What killed Pandion wasn't the market. It was the model.

What killed Pandion wasn't the market. It was the model.

Your round isn't a health signal. Pandion's $41.5M proves it.

Mar 18, 2026

Switch to T-Mobile for Business and get 10 lines for $15/mo. each

Switch to T-Mobile for Business and get 10 lines for $15/mo. each

Mar 16, 2026

Distribution Is the Moat

Distribution Is the Moat

HubSpot lost 75% of its blog traffic and had its best financial year ever.

Mar 12, 2026

The Flood and the River

The Flood and the River

Why most companies die doing too much

Mar 10, 2026

50M People. Still Can't Speak.

50M People. Still Can't Speak.

The green owl has a problem it doesn't want to talk about.

Mar 7, 2026

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