There’s a growing narrative that ex-founders make better investors. And it’s not hard to see where this has come from: ex-founders have lived experience, we’ve overcome challenges and navigated scaleups and exits. But this isn’t always the case. Founder experience can be just as much a liability as it can an asset, if ex-founders turned investors can only see a portfolio company through the lens of their own company, or if they aren’t willing to learn and adapt to new market forces that might be different to the one they’ve had success in.

The myth of empathy

There’s a persistent myth in VC that ex-founders are more empathetic to the challenges startups are facing. But there’s more to it than this. Just because I’ve faced a hiring crisis or navigated a long sales cycle doesn’t mean I inherently know what a founder is going through – and I would be foolish to assume I do.

A first-time CEO tackling European MDR compliance needs something very different from a technical founder navigating US reimbursement or building clinical evidence. Just because something worked in my company, or another portfolio company we’ve worked with, doesn’t mean it’ll map to another.

Context matters, and the industry changes, especially when we’re talking about companies founded in different market conditions. From team dynamics to healthcare policy changes – all of these variables shift the ground under our feet.

The danger is that founder-turned-investors can over-identify with their portfolio companies. That identification leads to projection: we start offering advice that’s relevant to our experience, not theirs. Ex-founders have to be careful that empathy doesn’t turn into ego.

Your role as an advisor

As an ex-founder, when you see a startup wrestling with a familiar problem – whether it’s pricing strategy, international expansion, or product-market fit – often your first instinct is to jump in. But I’ve learned that advice isn’t always what’s needed. In fact, it can confuse a founder’s own intuition and context.

At Nina Capital, we try to see entrepreneurs as our customers, not just investees. When you do this, your mindset shifts as an advisor: you hold yourself accountable to their experience, their outcomes, and their needs. You show up with empathy, respect their time, and genuinely strive to earn their trust. Fresh new questions carry a lot more weight than stale old answers.

Carrying over blind spots

Being an ex-founder doesn’t make you immune to blind spots. Often founders – more commonly in tech communities but sometimes outside too, are prone to making snap judgements in an attempt to innovate and get ahead faster. In the healthcare world, that speed led mentality isn’t always an asset.

Areas like regulatory nuance, reimbursement strategy, or clinician workflows aren't always core to a founder’s journey, but they’re vital areas of knowledge for a healthtech investor. At Nina Capital, we’ve built internal checks to challenge our own assumptions and ensure we strike the right balance between leveraging past experience and not relying solely on it.

Not having all the answers, but asking the right questions

Founder experience can be a huge advantage in venture capital, but only if ex-founders are willing to accept what they don’t know, as well as what they do. If we think our job is to recreate our own path through others, we’ll fail them. But if we stay curious, learn from new experiences, and respect the complexity of each founder’s journey, we can offer truly valuable insight.

Being an ex-founder doesn’t guarantee impact. But it gives you the opportunity to become a different type of investor. Ultimately, the best investors don’t have all the answers, but they help founders ask the right questions.

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