The professional investment game is relentless. No matter where you are in the world, you cannot escape the endless procession of markets. Sure, you can go on holiday and attempt the concept of relaxation, but each morning when you wake up, Wall Street has just closed. It’s impossible not to sneak a peek. Each month your numbers are measured against the market and your peers. There is no hiding. After 27 years and more than 50 reporting seasons, one of the mainstays of the Australian share market, IML’s Simon Conn, is stepping aside for a well-earned break. It might be permanent. It might be a refresh. Only time will tell. Conn joined IML back in 1998 - teaming up with market legend and past guest Anton Tagliaferro. Before long, Conn found himself overseeing the tough end of town - small caps. In those 27 years he has seen the rise of the internet, the smartphone, the GFC, COVID, and now the AI revolution. Through all of that, investors like Conn have been told it’s a new world. Concepts like ARR, PCV and the Rule of 40 have taken hold, while old measures like PE ratios have been pushed aside for revenue multiples. Meanwhile, the Small Ords index has underperformed for decades. It all sounds like a torture chamber, but somehow Conn has come through it, delivering 12 percent returns for more than two and a half decades. In this episode of Success and More Interesting Stuff, Conn shares the lessons he learned over his career and how he adapted his approach as markets evolved and over the past three decades.