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From a 2018 workshop to raising $560M
CEO Briefing #94

From a 2018 workshop to raising $560M

From a 2018 workshop to raising $560M
Short answer

A single 2018 pitch skills workshop at Microsoft in Berlin led Parloa CEO Malte Kosub to call Iskender Dirik years later for the Series A. Within two minutes, Malte’s natural confidence signalled success. The lessons: true founder confidence shows in small moments, and long-term personal branding means showing up authentically and adding value.

From a 2018 Workshop to raising $560M: What Two Minutes of Confidence Taught Me

Sometimes you can sense extraordinary success before you even know what someone is building.

In 2018, I gave a presentation on pitch skills at Microsoft in Berlin. Malte Kosub was in the audience. That was it – just another workshop, another room full of people listening. No personal interaction, no deep conversation.

Fast forward a few years. Parloa was preparing their Series A, and Malte reached out. He remembered that presentation from 2018, and that memory created enough trust for him to call me.

Two Minutes That Changed Everything

Normally, when I have calls with potential clients, I lead the conversation. I set the agenda, I guide the discussion, I establish the framework. That’s how these calls typically work.

But within two minutes of our first conversation, something completely different happened.

Malte immediately took control. Not aggressively, not awkwardly – just naturally. He set the direction of our call, spoke with complete self-assurance, and showed zero hesitation. At that point, I didn’t even know the details of what Parloa was building. He hadn’t presented any facts, metrics, or traction yet.

But I already felt he would be successful at whatever he was doing.

That level of confidence – the kind that shows up unconsciously in how someone carries a conversation – sends powerful signals. It was clear to me within those first moments: this founder operates at an exceptional level.

Two Parallel Stories

Last week, Parloa announced their Series D: $350 million at a $3 billion valuation. With total funding now exceeding $560 million, they’ve joined the top 1% of fundraisers globally. Malte and his team built that success through their vision, execution, and relentless drive.

But here’s what this story means for me:

Without that 2018 presentation – which was just me sharing knowledge with a room full of people – none of what followed would have happened. That one authentic moment, where I simply showed up and delivered value, created a foundation of trust that opened doors years later.

Because Malte remembered that presentation, I had the opportunity to support Parloa’s Series A, and was able to invest myself. None of that would have been possible without that single touchpoint from years before.

The Lessons

This experience crystallized two insights for me:

First: True founder confidence reveals itself in the smallest moments – in how someone leads a conversation, not only in the pitch deck they present. Those unconscious signals often predict success more accurately than any metrics.

Second: Long-term personal branding isn’t about aggressive networking or self-promotion. It’s about consistently showing up authentically and adding value. You can’t predict which moments will matter, but if you show up genuinely over time, the right doors will open.

I’m grateful to have been part of Parloa’s journey. And I’m reminded that patience, authenticity, and recognizing exceptional confidence when you see it – these are the things that create lasting opportunities.

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Episode page with show notes on id.vc

Frequently asked questions

How did Iskender Dirik start working with Parloa?

Malte Kosub attended a pitch skills presentation Iskender gave at Microsoft in Berlin in 2018. Years later, when Parloa prepared its Series A, Malte remembered it and reached out.

How does founder confidence show in a first conversation?

Within two minutes of the first call, Malte Kosub naturally took control, set the direction and spoke with complete self-assurance, before presenting any facts, metrics or traction.

How much has Parloa raised?

Parloa announced a Series D of $350 million at a $3 billion valuation, bringing total funding to more than $560 million.

What does long-term personal branding mean?

It is not aggressive networking or self-promotion. It means consistently showing up authentically and adding value, because you cannot predict which moments will matter.

Iskender Dirik
About the author

Iskender Dirik

CEO advisor for fundraising, exits and executive branding. Venture Partner at EQT Ventures, previously led the global Gen AI practice at Samsung NEXT and was Managing Director of Microsoft ScaleUp. Host of DEALMACHER, the podcast with the dealmakers who sat at the table when big capital moved.

EQT VenturesSamsung NEXTMicrosoft ScaleUp
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