on curiosity

The summer I spent in Barcelona was one of the most important experiences of my life. Like most college students studying abroad, I was excited about a "Cheeta Girls Summer". What I didn’t expect was that what I’d take away would have nothing to do with travel or language but with how to think.

My internship at a proptech startup started the day after I arrived. I barely knew the company’s name before walking into the office, jet-lagged and (embarrassingly) late. The moment I sat down, I realized that no one spoke English. I had taken Spanish for years, but the classroom had not done much to prepare me for the speed and complexity of real conversations in a working environment. That first day, I understood very little. I went home, convinced I wouldn’t last the summer.

But something interesting happens when you’re forced into a situation where you don’t know enough to pretend. You stop worrying about how you sound. Since I couldn’t talk much, I listened. At first, I asked only the simplest questions - enough to get through the workday. But as I got more comfortable, my curiosity took over. I started asking my coworkers about their lives, their weekends, and their opinions. I stopped filtering for what I thought was “smart” to ask and just asked what I genuinely wanted to know.

That’s how I got to know Núria, my boss. She had grown up in the Soviet Union before immigrating to Spain, and I was fascinated by her story. One night before post-work drinks, I wrote out a list of questions I wanted to ask her - big, possibly naïve questions about her past and how she saw the world. I brought that list to our happy hour the next day. When I hesitated, worried that some might come across as uninformed, she laughed and told me to ask anything. That conversation led to a weekly happy hour, and during my last week in Spain, she gave me a journal filled with books to read - her way of continuing the dialogue.

I think about that summer often, especially in my work as an investor. The same curiosity that helped me navigate Barcelona is what now guides my conversations with founders, LPs, and peers. Investing is an industry full of pressure to appear certain - to have well-formed opinions, to ask the “right” questions, to never admit what you don’t know. But I’ve found that my best investment decisions have come from doing the opposite. Instead of approaching diligence with a fixed lens, I approach it like my conversations with Núria by setting aside preconceived notions and asking questions that cut straight to what I truly want to understand. Why now? Why this market? What do you believe that others don’t? It's basically an exercise in first principles thinking but from a place of insatiable curiosity.

The same applies to my conversations with other investors. Some of the best calls I’ve had with my peers aren’t the ones where we exchange fully-baked theses but the ones where we openly challenge our thinking. How are you looking at this trend? What assumptions am I missing? It’s in these back-and-forths where we’re willing to be wrong, to ask the obvious questions, to push beyond the surface-level consensus that the real thinking happens.

What I learned that summer wasn’t just Spanish. I learned that the best conversations and the best thinking come from removing the fear of sounding dumb. Some of the most valuable insights I’ve had in my career have come from simply asking, How do you think about this? The ability to ask questions without hesitation and to be fully present in a conversation without worrying about how you’ll be perceived is a radically underrated skill.