How do you celebrate the fifth birthday of a high-flying tech start-up? By drinking for seven hours. At least that’s how Dovetail decided to do it. It was June 2022, and the customer analytics software firm had just announced its new valuation: $960 million.

After a day of celebration, Dovetail staff – including chief executive Benjamin Humphrey and its legal counsel Bethany Lo Russo – ended up at the Edinburgh Castle Hotel, a Sydney CBD pub popular with office workers. According to Lo Russo, Humphrey told her that he wanted to talk.