Simon Azzopardi

Simon Azzopardi walks through roughly twenty years, from a business degree taken because it was expected to a hundred-person agency today. Along the way: selling sweets door to door, an Oxford place won by administrative accident, and a software firm he helped grow to 150 people while someone else took the payout. Then an insurance startup, cut from sixty staff to four when COVID pulled its funding. And five children, arriving at once. It is for anyone weighing ambition against dependants.

1. 01Watching a founder sell for tens of millions while he could not afford a flat is what pushed him from services into products.
2. 02Organising events was a shortcut to learning. His first drew two attendees, his last six hundred, and the network outlasted both.
3. 03A career has roughly nine rungs — execution, management, directorship. He had done the first six well, and had never been in the room for the last three.
4. 04Mentors are stage-specific: he changes them as his problems change, rather than keeping one indefinitely.
5. 05The goal in his current business is to become unnecessary to it as fast as possible. A company that needs one person cannot grow.

Mentioned: Oxford · Microsoft Ventures · Startup Weekend · TechCrunch · Forbes · AON