Watching my niece, who’s now 15 months old, learn about the world around her, I was surprised to see how we, as “adults,” constrain the way she engages with her environment. We instill a sense of hesitation by setting perimeters around continued learning and development: “don’t do this, don’t go there, don’t touch that, put that down…”

It amazes me that the curiosity she has is lost in most people by the time they reach adulthood. Same with the level of courage. For example, knowing she’s going to fall, she starts walking, falls, gets up, hobbles, gains balance, walks a few more steps, falls, and repeats. As adults we have become embarrassed by public failure and too many missteps (pardon the pun) so we lose the confidence to try.

Thinking through this and how restraining these (self-) limitations can be, I set my slogan for the year: Be courageous. Stay curious.

Courage to make mistakes. To ask the wrong questions. To go against the grain.

Curiosity to strive to get to the underlying essence. To not taking things at face value.

Most interesting has been how this mindset has affected my interactions with entrepreneurs as I meet with them on behalf of SoundBoard Angel Fund. I’m no longer (solely) looking for investable companies and backable entrepreneurs. My goals in conversation are now:

  1. Learn from a great teacher (everyone has something to share) – keeping the curious mind open
  2. Connect with an exceptional founder/entrepreneur/leader/executive/technician
  3. Share a great conversation
  4. Push the other person to their limits – having the courage to ask the difficult questions

The movement towards this hasn’t been easy. Most people are quick to judge such an intense curiosity, taking it as a personal attack. I’ve learned to step out of each conversation and remind others where I’m coming from: a place of well intentioned, genuine curiosity.

In a sense, the Fund we have built to date has exemplified this, seemingly by accident. We dive into companies and really get our hands dirty during the diligence phase. Always shocking the entrepreneurs who didn’t think someone at our early stage would want to get so involved. However most of them express an appreciation and relief that someone cares enough about them to learn so much.

As I move forward in my career in venture investing, I will continue to strive to be both courageous and curious, to be comfortable with not knowing while endeavoring to find the answers.