Former Evernote CEO on the biggest mistakes tech startup leaders make

The rise and fall of AI startups

During the initial AI boom, the tech industry saw an unprecedented surge of startups with soaring valuations, driven by an influx of capital and the promise of breakthrough technology. The hype was bigger than anything I’ve seen in my career. But the real challenge was – and still is – translating that promise into tangible business impact.

Too often, companies get caught up in sprinkling AI whenever possible, expecting magic to happen. But technology needs to do more than increase efficiency – it needs to create new workflows, revenue streams and business models, while keeping the focus on the people who use it. When startups focus solely on growth metrics and investor expectations, they can lose sight of this integration. As once-booming startups struggle under the weight of unrealistic valuations, the cracks in their foundations—poor team cohesion, a lack of clear purpose—become glaringly obvious.

People First: A Philosophy Born of Experience

My philosophy of putting people first wasn’t something I learned from a business book; it was forged in the trenches of leading teams through triumphs and trials. Life is a team sport. Whether in families, organizations or businesses, the power of the team determines the outcome.

We have always believed that a cohesive team, one that shares a mission that matters and delivers aligned results, is the backbone of any successful endeavor. This lesson was hammered home while leading Google Canada. Industries were rapidly moving from analog to digital, and while the team was growing, it wasn’t reaching its full potential. We challenged them with a bold vision: to turn Google Canada into a billion-dollar business within two years. The initial reaction was disbelief, but the way the team came together to exceed expectations underscored the power of a common purpose.

We didn’t just track financial benchmarks; we strive to make the web work for Canadian businesses, to be the best and first in everything we do. This clearly defined The goal resonated deeply with the team and together, we not only hit that billion dollar mark, but surpassed $2 billion in three years. It wasn’t just about income; it was about the quality of the team, a sense of pride, a commitment to excellence and the mission that brought us together.

The consequences of underestimating people

On the other hand, I’ve seen what happens when companies lose sight of their people. A few years ago, I was brought in to advise a promising startup. They had just raised tens of millions in a week – a staggering achievement by any measure. But despite their success, there was a glaring problem: The founders were so focused on growth that they neglected the importance of building a strong, cohesive team, opting instead to micromanage everything and everyone.

The result was inevitable. The company grew rapidly, but the internal culture was toxic. Turnover was high and despite the influx of capital, the cracks in their foundation became too big to ignore.

Navigating market changes and economic downturns

I’ve been through my share of rocky economic climates, and during these times, a people-centric approach becomes even more critical. Maintaining team morale, being transparent with your people, and making tough decisions keep the company aligned with its mission. This was most evident during my time at Evernote, which was burning through cash at an unsustainable rate when I took the helm.

We’ve had to make tough cuts, but we’ve done it with the empathy and transparency that underpins a strong team culture. It wasn’t easy, but it was the right thing to do, ultimately supporting our team’s focus on helping the company survive in the face of adversity.

Building teams with a united purpose

So how do you build a solid base of people for lasting success? It starts with intentional hiring—bringing in people with the right skills and who align with the company’s values ​​and mission. Leadership plays an essential role here. It’s not just about setting a vision; it’s about over-communicating and reinforcing that vision through every decision, engagement and action.

At data and AI company GrowthLoop, where I’m currently CEO, the culture we’ve built directly reflects our commitment to people-first leadership. We don’t just focus on metrics or growth; we are equally dedicated to building a team that truly cares about each other and is obsessed with customers. One of the most telling aspects of our culture is the weekly World Fair meeting where we highlight customer needs and wins and team members share their appreciation for each other. These aren’t just empty gestures, they’re a true recognition of the hard work and collaboration that drive our success (and, frankly, a highlight of my week).

Equally important is our commitment to open communication. We encourage team members to voice their opinions, especially when they disagree. Through these honest conversations, we find the best solutions. And despite any differences, we always come together and move forward as a focused team, united in purpose. This atmosphere of mutual respect, recognition and open dialogue empowers us to deliver incredible value to our customers and partners.

A lesson for future leaders

If there’s one essential lesson we’ve learned, it’s this: sustainable success comes from building a people-centric culture from day one. Future startup leaders should focus not just on what they build, but how they build it—making sure their teams are cohesive, their purpose is clear, and their leadership is authentic and committed to over-communicating.

The old flex was the size of your team. In today’s market, the new flex is how small and efficient your team can be while maintaining a people-focused culture. The difference between a success story and a short (lived) story is how a business embraces small, agile teams united by a common purpose and driven by a mission that matters.

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