From Founder Failure to Building a €100M+ European VC Fund with Apostolos Apostolakis, Managing Partner @ VentureFriends

Happy Wednesday from James Pringle, Hector Mason and the Riding Unicorns team!

In this episode, we’re joined by Apostolos Apostolakis, the founder-turned-VC behind VentureFriends, a pan-European pre-seed and seed fund known for backing consumer and fintech breakouts like Plum, Blueground, Huspy, Carmoola and Instashop.

Apostolos shares a remarkable story of resilience — from scaling a startup to €100M+ in revenue and 500 employees, to facing bankruptcy and rebuilding his career with a major exit, prolific angel track record, and eventually launching one of Greece’s most successful VC funds.

We dive into:

💥 Lessons from scaling fast… and failing hard
 🏗️ Rebuilding after burnout and public failure
 💡 Founding VentureFriends and filling Europe’s early-stage funding gaps
 🌍 What it’s like running a distributed VC firm from Athens
 🤝 How to support founders without overreaching
🎯 The evolution of his founder selection playbook
🔎 Why grit, clarity of thinking, and mission-driven ambition now matter most
🦄 His unicorn pick? Carmoola — and the story behind QED’s entry

This is a raw, thoughtful, and inspiring episode for anyone navigating the highs and lows of the startup world — whether you’re a founder, investor, or just deeply curious about the human side of VC.

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Have a great Wednesday,

The Riding Unicorns team