CEO Confessions

My biggest mistakes, views on VC’s, red tape and people.

Startups Magazine went straight in for the kill in their interview with me. I did my best with the answers.

What is the hardest thing you’ve ever done? What was your biggest business mistake? What is the most common mistake that entrepreneurs make? What would make you a better leader? What do you wish you’d known when you started?

Startups Magazine went straight in for the kill in their interview with me. I did my best with the answers.

Here are some of the highlights

What is your greatest business achievement?

It has taken me 10 years to get the team around me as good as it is today, and I think assembling a group of people this talented, this engaged and this excited about our future, is my best achievement. It’s the hardest too.

What do you do every day?

I spend most of my time thinking about our people and organisation structure and our market. It’s my job to design the organisation so our people can do their very best work, and to see where our market is going so that we’re sailing in the right direction and we can make the big bets on the future in the right places.

What is the hardest thing you have ever done in business?

By definition, entrepreneurs create value and opportunity where other people don’t see it. That means you’re often the only person in the room who believes something can be done and should be done. I think the hardest times are when everyone you trust around you thinks one thing and you believe you need to do another — they are the real test of your leadership. Fundamentally, my approach is to counsel widely, listen carefully, then do what I believe is right.

Biggest business mistake?

Oh — there are so many. Do I have to pick one? Back in 2010 when we were 90 people I tried to take myself out of the day to day and it was far too early, we weren’t ready. We had no product team at the time, just me and the engineering team and I moved them to report to the CFO.

It was a disaster, we didn’t really build anything for about 18 months. I still cringe when I think of that decision now, I must have been out of my mind!

What one thing do you wish you’d known when you started?

I knew almost nothing when I started but I don’t really have any big regrets. I think you just make the best decisions you can on the day, stay true to your values and keep learning. I guess in the last few years I’ve really seen how much better my judgement on those hard issues when I’m rested and in a good space mentally. So maybe I’d tell myself that — prioritise good sleep!

What is the single most important piece of advice you would offer to a less experienced entrepreneur?

It’s the best job in the world but sometimes it’s the loneliest too. You need to be ready for the hard times when you’re filled with self-doubt and dig deep, get the courage to do what you think is right and remember to constantly iterate and adjust your course as you need to. “Fix in flight” is what I call it.

What would make you a better leader?

I think time makes me a better leader — you can’t beat experience. Every month that goes by, I’ll do something else imperfectly and learn something for the next time. If you’re genuinely open minded, time is a great trainer.

Read the full article over on Startups Magazine.

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