Riding Unicorns: Venture Capital | Entrepreneurship | Technology
Riding Unicorns is a podcast featuring the world's best minds from venture and startups. Hosted by VCs James Pringle and Hector Mason, the show explores what it takes to build and back successful tech unicorns. Each episode features conversations with top founders, operators, and investors unpacking the strategies, challenges, and insights behind scaling category-defining companies. From fundraising and product-market fit to hiring, growth, and beyond, no topic is off-limits. Whether you're a founder, VC, angel investor, or just curious about the world of startups, you’ll find valuable takeaways in every episode.
Riding Unicorns: Venture Capital | Entrepreneurship | Technology
From Founder Failure to Building a €100M+ European VC Fund with Apostolos Apostolakis, Managing Partner @ VentureFriends
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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.
