Today, we’re tearing down the glossy myths surrounding startup success and embracing the glorious, messy reality of being wrong 🧐.

Rowan Simpson, an authoritative voice who has been at the very heart of some of New Zealand’s most important technology companies, is an author, investor, and advisor, but, crucially, he was an early employee and shareholder at both Trade Me and Xero ✨. He’s earned the right to challenge conventional wisdom, having also helped guide ventures like Vend and Timely to colossal success.

Simpson argues that the history we read about rapid growth isn't fact—it’s narrative. The painful stumbles and backward steps? They usually get erased, leaving others starting out surprised when the hard moments happen to them, too. If told honestly, he suggests, the unvarnished inside stories would be tedious, plodding tragedies rather than epic heroes’ journeys 🎭.

Imagine the triumphs of Trade Me and Xero. We picture flawless execution, but Simpson reveals how close they came to failure 😱. Trade Me, for instance, was fragile just two years in. Its initial model—free classifieds supported by advertising—failed to generate the necessary revenue, nearly forcing a shutdown. Three of the original four team members even left! 🤯 Xero, too, languished below its IPO price for several years, relying mostly on modest traction localized in New Zealand. And remember Vend? After raising over $35 million and hiring 250 people, the company came “very close to shutting it all down” by the end of 2015.

These ventures were nearly tragedies, and that’s where the most profound lessons are found. Success, according to Simpson, isn't about perfectly navigating the market. It’s about finding opportunity in uncertainty and embracing the truth that achieving ambitions involves being repeatedly wrong en route. He champions “the quiet ones”—the collaborators and clear-sighted figures working behind the scenes, contrasting them sharply with the myth of the lone, charismatic genius 💡. He asks us to follow the mathematician Carl Jacobi's guiding principle: "Invert, always invert."

If you’re a founder tired of comparing your grueling startup grind to a smooth blockbuster movie, this episode is mandatory listening. Stay tuned, because we are about to reveal why sometimes, the only way to be right is to get deeply comfortable with the idea of being wrong. Don’t go anywhere. 🎧