The Angel Diaries: What 60 Angel Investments Really Teach You – Failures, exits, and the patterns you only see with experience

With 60 angel investments and 140 investment rounds, Simon Thorpe has seen almost every outcome an early‑stage investor can encounter – from meaningful exits to painful failures. In this candid conversation, Simon shares what those outcomes have really taught him, and how his approach to angel investing has evolved as a result.

Rather than focusing only on the wins, this session goes deep into the failures: why they happened, what signals were missed, and how those lessons reshaped Simon’s decision‑making. Alongside this, he reflects on the successes – what worked, what repeated itself, and what he now looks for when backing founders at the earliest stages.

This interview is a rare opportunity to hear an experienced angel speak openly about the full distribution of outcomes, and how long‑term investors build judgment, resilience, and discipline over time.