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The Best Mistakes I’ve Made: Ex-Idealog editor Matt Cooney on why ‘you’re only as good as your next venture’

Here’s what Matt Cooney, Idealog’s editor from 2005 to 2011, had to say about the subject in an editorial back in 2011. 

Ten years ago I was leading the development team at a well-funded tech startup. We had a lot going for us: a decent track record, a talented team with some genuine superstars and an existing revenue stream. We were ambitious and we had a brilliant business plan that just couldn’t go wrong.

As you’ve already worked out, dear reader, this venture failed, and the sometimes starry-eyed investors who stuck with the company eventually sold their stake for about one-twentieth of their investment.

The reasons are complex, but unremarkable. Failure is the constant companion of entrepreneurs, risk-takers and dreamers. Those who deal with it best are perhaps those most likely to succeed, and those who haven’t made mistakes probably haven’t made anything.

Mistakes certainly don’t faze Rowan Simpson. You might think it shouldn’t: Simpson was an early employee and shareholder at Trade Me and cashed up when Fairfax bought the little auction site. He had an early strategic and investment role at über-startup Xero, and now spends his time consulting and investing through his own investment vehicle.

Rowan writes frankly about his Trade Me and investing experience. It’s a must-read for anyone in or planning a tech startup, but it’ll be enlightening for all Idealog readers. Even for serially successful people, mistakes and missteps—sometimes fatal, sometimes fortuitous—are facts of life. It’s often only in retrospect that we know what we got right and what we got wrong.

Geoff Matthews would understand. He has a simple formula: find companies with great products that are under-performing and give them a serious dose of capital, business smarts and, most importantly, ambition. It’s not always the Kiwi way, he tells Vincent Heeringa. “As a consultant I became frustrated that we’d suggest all these ways to grow businesses but the owners would shelve the idea because they couldn’t implement them. It’s such a common story in New Zealand—we’d see all these great ideas and ask, ‘What’s stopping you?’ Capital and courage? Well, that’s easy to fix.”

That includes courage to look beyond mistakes and see the big picture. That decade-old failure still rankles sometimes, but the former staff have gone on to great things in great companies and their own startups. Truth is, you’re only as good as your next venture.

  • This story was originally published on June 1, 2011. 
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