Watch: Rowan Simpson’s Three ways to be wrong

Rowan Simpson has been in the thick of it. He was employee number three at Trade Me, where he was involved in the machinations over its $750 million sale to Fairfax, and head of product at Xero before becoming an investor and director in software firms Timely and Vend, which sold for $135m and $455m respectively.

He now co-chairs Hoku Group, which combines investments in early-stage companies with philanthropy.

In the video above, he shares three tips he gives the founders he works with today.

And, in a nod to his recently published book (read an extract here), he outlines three ways to be wrong.

“One is to lie, and that’s surprisingly common in start-ups where people know that something’s not working, but pretend that it is and hope that other people don’t notice.”

It’s the old “MVP” – minimum viable product – jape, where some of your features, or promises, just aren’t actually viable.

“Common advice for founders is, ‘Fake it ‘til you make it’,’ he told the Herald.

“A much better approach for a founder approaching an investor – rather than pretending that you already have the answers – is to be clear about the things that you don’t know yet and that you want their help to find out.”

His top tips – or ways to be right – include looking for an investor “who can push you forward with a bit of money, but mostly with time and advice”.

He adds, “Don’t start with the technology. Start with the customer and work backwards to the technology. Don’t define yourself as a technology company, because it’s 2025; every company should be a technology company now. It’s not the thing that will make your company interesting. What makes it interesting is the problem that you solve for people.”

His own biggest blunder: The Corin, Corin, Corin incident

What was Simpson’s most embarrassing mistake? It happened in the 2000s during Trade Me’s early years and involved broadcaster Corin Dann – then a junior reporter with TVNZ.

“When you’re working on a fast-growing company, you have to constantly trade off between fast and good. Going fast means making compromises, and sometimes you get things wrong and you have to adjust quickly to that.”

“[Dann] contacted us about a story he was working on. We offered to help with the visuals for his story by updating one of the listings so he appeared to be the seller,” Simpson says.

But a programming mistake meant every single member in the Trade Me database was instantly renamed Corin.

“We felt suddenly ill. After taking a moment to compose ourselves, we took the whole site offline. Thankfully we had a regular back-up which was only a few hours old, but it would take time to restore.

“Meanwhile, the mistakes compounded. In our panic, we overlooked that the automated process to close completed auctions and notify the seller and winning bidder had continued to run in the background every minute. The emails that were generated for this purpose created fresh confusion. ‘Hi Corin,’ they all started. ‘Your auction has closed. The winning bidder is Corin.’”

Early Trade Me, Vend and Timely staffer Rowan Simpson now invests in start-ups. With his new book, he shares some of the advice he gives the founders he work with.

An explanatory apology email was drafted, but “almost immediately after pushing send on that message, we realised a further mistake,” Simpson said. “If we’d paused and tested that first, we would have discovered that the script also relied on the names in the database. Thousands of emails apologising for a previous message which had been mistakenly addressed to Corin and named the winning bidder as Corin, all once again started: ‘Hi Corin’.”

“Many start-up founders quote the memorable Facebook motto ‘move fast and break things’ without a thought for just how embarrassing it can feel when you’re picking up the broken pieces.

“I’ve told this Corin story countless times over the years, including in a keynote at Microsoft’s TechEd conference in 2006. It has become part of Trade Me lore. And it has helped me to console lots of other founders after they have made their own silly mistakes.”

Chris Keall is an Auckland-based member of the Herald’s business team. He joined the Herald in 2018 and is the technology editor and a senior business writer.