Riding Unicorns: Venture Capital | Entrepreneurship | Technology · Riding Unicorns Productions

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

June 18, 2025·34 min·2 clips

Apostolos says the company reached 100 million in revenue, then faced chapter 11 and creditor negotiations.

1. Riding Unicorns: Venture Capital | Entrepreneurship | Technology features Apostolos Apostolakis discussing VentureFriends and his path from founder to investor. 2. Apostolos Apostolakis is the Managing Partner at VentureFriends, and he matters because he built the firm after operating and angel-investing roles. 3. The episode asks how a founder failure, a successful exit, and a Greek VC platform led to VentureFriends’ investment strategy. 4. Apostolos says VentureFriends invests at pre-seed and seed, started in Athens nine years ago, and now has colleagues in London, Warsaw, Barcelona, and Athens. 5. He says the firm has raised three funds so far and is now raising a fourth fund that will be active after the summer. 6. He describes his first company as a big initial success that later became a painful failure, with 100 million in revenue and 500 employees. 7. He says the company could not honor obligations to banks and entered chapter 11 after the Greek crisis cut sales and GDP. 8. He contrasts that collapse with a later food-delivery marketplace that sold to Delivery Hero within five years. 9. He says the exit led him into angel investing, including TaxiBit, which was sold to FreeNow through Daimler after buying Halo in the UK. 10. He says founding VentureFriends in 2016 came from seeing a gap in Greece’s funding ecosystem and realizing early-stage funding is local. 11. He says the failure period felt like his life stopped for three to four years, with no social life and a long period of shame. 12. He says the crisis made him think that if the first company had worked out easily, he might not have kept the same drive. 13. He says running VentureFriends from Greece requires more travel, but the team offsets that with local presence in the UK, Poland, and Spain. 14. He cites Hummingbird’s decentralized style as an early model and says great funds need to be present for the companies they choose. 15. He says time management changed as VentureFriends scaled to 20 investments per fund and the team had to learn to let go. 16. He says the team now gives most time to founders who are strong, independent, receptive to evidence, and quick to execute. 17. He says VentureFriends became stricter over time about team selection after earlier idealism around business models and markets. 18. He says the interview style is reflective and practical, with many questions about founder motivation, adversity, and decision-making. 19. Founders, early-stage investors, and operators in European tech would likely value this episode. 20. Listeners wanting sales tactics or a pure macro market debate may skip it.

Listen to the show on

Apple Podcasts Spotify

Play clips from this episode More from Riding Unicorns: Venture Capital | Entrepreneurship | Technology