Jeevs Mahil decides which coaches get put in front of Octopus Ventures' portfolio founders, and after years of those introductions she has a clear, slightly uncomfortable view on why so many founders pick the wrong one.

James and Jeevs get into why "ex-founder" tells you almost nothing useful about whether someone can actually coach you, the one question to ask before your first session that most founders skip entirely, and the real ROI behind getting this call right versus wrong. Get this one wrong and it costs a lot more than the coaching fee.

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A founder writes in feeling off track and wants to know if the problem is his plan or his execution. James Johnson and Freddie Birley don't let him off with "it's both."

They walk through how to tell which one is actually broken, why most "plans" fail the moment someone asks how often you're checking against them, and why the instinct that got you through Seed can be the exact thing working against you at Series A. Stick around for the rocks-and-sand analogy, which might explain more about your last quarter than you'd like.

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Three exits in, Alex Fenton knows exactly what buyers look for, and it's not what most founders think. James and Alex talk through keeping every door open, why a three year plan beats a five year one, and the blunt piece of feedback from a manager that changed how Alex leads. Including the real difference between planting seeds and planting saplings when you're building a team built to last.

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