Harley Miller left Insight Partners after nearly a decade to build Left Lane Capital as his own entrepreneurial venture, conducting roughly 2,500 LP meetings to get the firm off the ground while training his entire team to use tools like SQL and Alteryx so they can analyze complex datasets at the speed of a tech company's analytics team. He defines conviction as being so resolute that nobody can tell him he's wrong, then works backwards to pressure-test that belief, leading to unconventional bets like Freestyle Chess and putting his personal reputation on the line for deals like EquipmentShare when he believes strongly in founders.