Upper Bound has become one of my favourite annual trips. This year, more than 11,000 AI geeks and aspiring geeks gathered in Edmonton. I had the chance to give a main stage masterclass called Calculating Risk, Maximizing Upside. Many people are perceived to be risk averse. Over the...
One of the most powerful frameworks I’ve come across is the Rule of 3 and 10, coined by Hiroshi Mikitani-san, founder and CEO of Rakuten. The idea is simple: every time a company triples in size, everything breaks. As Rakuten grew from a handful of people into a global business, Mikitani-san...
A swimming world champion, a cycling champion, and a marathon champion each tried their hand at a triathlon. None of them even came close to the podium. All were easily defeated. Why? Because the swimming champion could not bike, nor could he run fast. The cycling champion did not swim...
In many companies, the bottleneck isn’t necessarily in the execution of decisions. The real bottleneck is the excessive time people waste making decisions. When I was Wattpad’s CEO, everyone in the company knew I had a simple 2×2 framework to empower the whole team to make fast, high-quality...
Sonos replaced its CEO last week. The company faced significant backlash after launching a redesigned app earlier last year that was plagued by bugs, missing features, and connectivity issues, frustrating customers and tarnishing its reputation. This also led to layoffs, poor sales, and a...
In 2006, Wattpad started as a simple mobile reading app, mainly for classic books. Fifteen years later, it evolved into a global, AI-powered, multi-platform entertainment company with numerous blockbusters before being acquired. As you can imagine, my role as CEO at the start of Wattpad—when it...
As a refresher, a CEO does only three things: Sets the overall vision and strategy of the company and communicates it to all stakeholders. Recruits, hires, and retains the very best talent for the company. Ensures there is always enough cash in the bank. These responsibilities might...
I’m a 3x entrepreneur. I was the CTO of my first company, which failed. I was the CEO of my second one, which was acquired when it was still very tiny. Wattpad was my third and last company, but it was my first one as a scale-up CEO. It was a very different beast. The learning curve for me was...
When you work at a startup, seeking advice and gaining buy-in from the broader team can help you move faster … until it becomes a crutch. Recently, I bumped into an entrepreneur I invested in. He’s making some changes to the direction of his company, and after explaining them to me, I pointed out...