Social radar

Lately, I’ve been reading about early-stage startups and entrepreneurship. It might be the effect of last month’s “founder mode” hype in the tech community¹, but I’ve always been curious of the kinds of people who become entrepreneurs—what’s different about their thinking or life experiences that pushes them into this space? This is the kind of people pattern I’m super interested in, but this post isn’t actually about that.

My curiosity about founder mode led me to read more of Paul Graham’s essays, and one about Jessica Livingston² stood out to me. I found it quite special and moving. Somewhere down this Paul / Jessica / Y Combinator rabbit hole I discovered that Jessica was a guest on Lenny’s podcast.

In that episode, Lenny and Jessica talked about her mysterious “social radar”—a nickname she earned for her uncanny ability to read people. At first, I was more interested in what she had to say about picking which founders to invest in (worth a listen, by the way), but this radar thing overtook my attention.

What’s fascinating is how hard Jessica found it hard to explain this skill, or even how she developed it in the first place. It’s a soft skill that’s tricky to put into words, like a tacit knowledge you absorb rather than learn step-by-step. Maybe “intuition” is the best word for it, but that doesn’t seem to give her enough credit. It’s intuition mixed with years of practice observing and analyzing people and relationships.

From the conversation, it sounds like Jessica’s skill benefits from her heightened sensitivity to other people’s emotional states and the underlying dynamics between individuals—intangible things that are hard to validate or measure. This raises the question of whether such a skill can be acquired, or if it requires some innate talent to begin with.

I thought of an article I read on indicator species, particularly the part where the author talks about people with SPS (Sensory Processing Sensitivity) and the benefits of sensitivity. From an evolutionary perspective, the advantage of highly sensitive individuals are:

[…] they noticed minor differences in taste, smell, sounds in their environment faster and easier; they were more prone to recognize hints of behavior or emotions that could have threatened the group; they observed opportunities and solutions that others missed; they processed their decision-making more deeply before acting.

Maybe Jessica belongs to the 10-20% of the population who are more perceptive and sensitive to their environment. This would certainly align with her role at YC, where her radar was indispensible to selecting successful ventures. As Paul writes, “The earlier you pick startups, the more you’re picking the founders.” He also credits Jessica for creating the family-like culture at YC that made it so special in the early days.

I wonder if this kind of tacit knowledge is similar to what actors draw on in their craft. Good acting is essentially about stepping into someone else’s mind and embodying their emotions and behaviors. This requires skilled observation and capturing the tiny details just right: how someone moves, their manners, the subtle shifts in their facial expressions, and let’s not forget microexpressions. I’m sure there’s much more to it than I can even fathom.

When Lenny asked Jessica for advice on developing this kind of skill, she simply said, “just pay attention and observe.” It was a short, to-the-point answer, and it made me think that she probably doesn’t get asked about this very often—something she confirmed when she reposted the episode on X. Maybe this is a reflection of a culture that doesn’t value soft skills like this as much as we say. Otherwise, why haven’t more people asked about it?

Yet, it’s a valuable skill worth learning, honing, and talking about, as evidenced by Lenny’s enthusiasm and the comments from others. So, here’s my interpretation on what Jessica means by “pay attention and observe”:

• Listen deeply to other people. Don’t just hear their words; try to understand the deeper meanings behind what they’re saying. What are they communicating with what they’re not saying?
• Be curious about people’s inner worlds. Ask questions like, “Why do they behave the way they do?” and “What drives their actions?”
• Pay attention to people’s body language. I don’t know much about this subject, but there are many videos of experts analyzing body language that show there’s science behind it.

Maybe Jessica will share some videos where she live-analyzes founders during interviews—that could illuminate a few things.