Friday Funism – “Smiling Killer”

One of my favorite descriptions we use half in jest is that a founder seems like a “smiling killer”. This is a compliment, I promise.

This means that the founder strikes a very delicate balance that is very hard to pull off. First, the founder just seems like a great person. She is kind, charismatic, engaging, and seems genuinely great to work with. These are super valuable skills because the job of the CEO is largely about working with people. This includes both influencing external customers, funders, or team members and motivating a high-performance team. These are all made easier if people genuinely like or admire someone.

Selfishly, it makes our job a lot easier when we feel like we can build a great rapport with a founder, and have a trusted, open dialog with him to bring out the best in each other and ultimately, in their company.

At the same time, it’s critical for founders to also have a high degree of competitive drive and killer instinct. Venture backed startups are very unforgiving, and the most ambitious companies are fraught with risk and uncertainty. There is tons at stake, not the least of which is the time and energy of the talented people that devote years of their life and choose to work below their market cash comp to advance a company’s mission.

For this reason, it’s critical for founders to be ruthless about managing their time, be willing to make hard decisions about team members that aren’t performing, and to be willing to fight ferociously to achieve important wins. They also need to have great commercial instincts, be able to maintain great fortitude when things are going poorly, and be willing to move aggressively to capitalize when things are going well. And all this while incumbents and competitors are trying their very best to destroy them at the same time.

The other thing we often think about is that founders aren’t fully formed when we meet them or even when we fund them. A lot of founders grow into their own over the course of running their business, so it’s part of our job to enhance their raw abilities and experiences to be able to tackle the expanding challenge of startup leadership. Similarly, some founders can be very effective even if we personally don’t immediately “click” with a founder, or find them a bit difficult or off-putting at first.

I actually find that many of the strongest founders put us “on our heels” initially because of their intensity or competitive drive. We’ve learned not to shy away from this, but to actually seek it as long as we get comfortable that we can develop a strong working relationship over time. We also are lucky to have a partnership with some distinct personalities, which may allow a founder to better resonate with someone else on the investment team if there is likely to be a better personality fit (see our fun-ism on handoffs).