Though I’m still a junior VC, I’ve had the privilege to meet with >100 entrepreneurs and learn more about their vision for the future. That 100+ isn’t a massive sample, but there’s an important commonality amongst those I’ve found really impressive – a mastery of some of the inherent tensions in being a startup entrepreneur. They manage to strike a balance between poles that, taken to their extremes, can endanger their business. They build paradoxes out of what could be contradictions. Here are a few examples of those paradoxical characteristics:

• Insatiably curious, but biased towards action. Brad Feld referred to these kinds of CEOs as learning machines. They manage to learn something valuable from nearly every interaction – even if the person isn’t directly in their industry, or familiar with the challenges they’re trying to solve. During our diligence, which has perceived goal of allowing us to learn about their company and worldview, these CEOs were almost equally as inquisitive as we were – asking for our input, and trying to learn from what we’ve seen in the market. But that desire to continue learning didn’t manifest itself in ‘paralysis by analysis’; they understood how much knowledge was sufficient to inform their first actions, knowing that the most valuable lessons come from customers and the market.
• Rational and honest, but with a clear point of view. More than any other CEOs, they were the first to admit what they didn’t have figured out and what risks kept them up the most at night. They approached their business rationally, had a clear sense for what questions an outsider would wonder about, and were open about the degree of certainty they had in their answers. This rational approach was mixed with a passion for the problem they were trying to solve and clearly thought through hypotheses about the answers they had selected and why. The combination of these traits creates a clarity that allows them to execute against the biggest risks, and seize the biggest opportunities.
• Deeply understands all functions, but allows team members to have ultimate ownership. These CEOs showed a clear grasp of the major happenings in the business – the strategies for each function, the big experiments running and the important metrics. But, just as important – they recruited world class teams to build their visions (often including folks from previous ventures), and gave them the freedom to execute quickly. I’ve written previously about how transparency and decentralization can provide organizations with a speed advantage – and these CEOs demonstrate that daily. One interesting early indicator of this is how comfortable a CEO is letting their team field questions, without feeling the need to cut them off or correct them (if the substance of what they said is correct).

Would love to hear if there are some other tensions you think great CEOs must master – you can find me @ablordesays.