Why weak Product-Market Fit is quietly destroying your Go-To-Market strategy (with Chris Tottman of Notion Capital)

In this episode, we’re joined by Chris Tottman from Notion Capital. Before becoming a VC, Chris co-founded MessageLabs and helped grow it into a $700 million exit, so he’s seen the startup journey from both sides of the table. We talk about what really happens when your product-market fit starts to slip—and why it quietly wrecks your entire go-to-market strategy. Sales start missing targets. Marketing can’t get traction. Churn creeps up. But most teams keep pushing forward without realizing the core problem is the product just doesn’t fit anymore. (00:00) - Introduction (09:55) - Common mistakes in Go-To-Market strategies (19:54) - Identifying a VC case (30:05) - Importance of Product Market Fit (39:38) - Transitioning from VC to PE (50:07) - Next week: pricing changes