A dance with serendipity

How Nicole Ruiz’s path from Twitter to VC to homemaker exemplifies “the life of the mind”

Welcome to today’s installment of “Fantastic Builders and Where to Find Them.”

Builder Spotlight: Nicole Ruiz

Principles on display: radical agency; your life as the measure of all things; be intellectually ambitious; we build ourselves by building

Nicole Ruiz is a community builder. She’s a full-time mother who hosts dinner parties, who gets to know her neighbors, and who keeps an informal social CRM on local people. In a world where people complain about fragmentation and isolation, where people leave the house less, where child-raising villages are the exception rather than the rule—Nicole is quietly building these things for herself.

Her path to this point is a classic case of Steve Jobs’ “You can't connect the dots looking forward; you can only connect them looking backwards.” Even looking backwards, it looks less like a carefully charted course, and more like a dance with serendipity. A dance of striking complexity and skill, no less, which Nicole has continuously honed in the context of ever more stimulating and demanding dance partners. (I was lucky enough to hear Nicole tell her story while her unbelievably cute toddler was playing next to her and occasionally inquiring about yogurt or Amtrak trains.)

Growing up in Fairfax, Virginia, Nicole benefited from having a high bar of intellectual inquiry set in her K12 education. She went to Trinity Christian School, which was rooted in a classical education approach and emphasized “learning how to learn,” as Nicole recalled. For example, one of her senior year assignments was to write a thesis explicating her “worldview” and what she was “called to in the world”:

We had to defend that thesis in front of a board of adults. And you had to interview people in specific careers. So I interviewed somebody at Google who was working on their machine learning team.

More than that, Trinity had the killer combination of highly invested teachers and a liberal arts approach:

I would also say so many of the teachers just really cared about the students. In fourth grade, I did a Girls on the Run 5k with one of my teachers. My parents were like, “Don't ask your teacher. That's so embarrassing.” But my teacher said, “I would love to do that with you.” We stayed in touch for years.

That education was very formative for me, and I think set a really high bar. They also talked a lot about the life of the mind. There’s a richness that the liberal arts lends to your life and to your world…. You kind of have this perception [that] the life of the mind is woven through your world at large.

This idea of building a “life of the mind” really stuck with her, and gave her a deeper, more expansive view of what constituted a good life: not the accumulation of some narrow set of credentials or job titles, per se, but rather an intellectually curious, independent-minded, community-driven orientation that infuses all your projects and decisions.

This, along with a volatile family situation requiring her to make her own way after high school, motivated what ended up being a very atypical path through higher education, into her career, and, ultimately, back out of her career.

Nicole’s experiences of higher education included several stints at community college, a 1-semester stint at Liberty University (before dropping out in bitter disappointment), and a data science certificate program at Lambda School (from which she also dropped out). All of these experiences left her wanting for the intellectual stimulation and “life-of-the-mind” atmosphere she had learned to expect at Trinity.

So she turned to the internet, specifically Twitter, to fulfill those needs. She had been on Twitter since high school, but now she started to post a lot more, sharing ideas and articles related to her burgeoning interests in medical research and machine learning.

The time that most people spend hanging out with college friends, Nicole spent hanging out with Twitter mutuals, particularly from the post-rationalist Twitter scene. Buoyed by those initial connections, she started “trying to throw myself into more things on the internet that were interesting,” which led her to get some scholarships to attend scientific and engineering conferences that she was interested in. When she attended conferences, she networked and took notes and asked questions, which in turn led to work opportunities:

I used to also go to events and just take notes like crazy. I kept them if I thought the speaker was really interesting, so that I could message the speaker. Just to prove that I was competent and paying attention.

I would also try to ask questions that made me visible to both the speakers and other attendees. I think more people spoke with me at events like these because it was easy to follow up on the public questions I raised my hand to ask.

One time I was in some lecture at the Google offices in DC, and I was taking really intense notes, and one of the people from that group came up to me afterwards and just started chatting. He was like, I like your notes. What did you write down? What did you think? And we started talking, and they were like, do you want to work on this project?

Nicole did a fair amount of work during this period in data-driven medical research. And she did even more ad hoc learning as well, crashing her friends’ lecture courses at Georgetown or UChicago and talking to the professor afterwards. She noticed how easy it was. “Nobody cared” that she wasn’t enrolled. “You could literally go up to the professor and be like, I sat in on your class. I have these questions. And they were like, ‘That's awesome. What did you think?’”

In the midst of all this very-cobbled-together college-level education, it was her Twitter habit that kickstarted her career.

I was in the middle of the Lambda School boot camp, and I was tweeting, should I work at a FAANG [big tech] company? I was still really interested in machine learning and health care. And so [the man who would become] my boss, Michael Dempsey, who [was then] the GP at Compound, the VC firm, ended up reaching out to me and just DMing me. He said, “Don't go work for a FAANG company. That's a horrible decision. It's going to kill your creativity. And have you thought about VC?” And then we jumped on a call, and that's how everything progressed… They were very open to me proving my grit through the application process and proving how fast I could learn, and I ended up getting hired.

He had followed me for a while, and I loved his tweets on technology. For a long time I would post: machine learning paper, machine learning paper, here's my prediction for how companies will adopt this. And then I would link when whoever it was, Microsoft, Google, whatever big company would follow up and do something that I thought was a confirmation or was otherwise related to the research I had posted. Michael would interact with those occasionally. But that was really all the context we had.

By doing her very Nicole-ish dance of sharing her notes on Twitter, Nicole had in effect created a public resume of time-stamped, provably accurate bets on the commercial potential of emerging AI technologies. This is the kind of track record that a VC firm can usually only dream of when vetting a young candidate.

Nicole worked as a VC, intensely, for 3 years. She loved it. It was the culmination of years of the sort of high-agency networking and learning-in-public that so often characterizes builders’ paths today.

But in the background, another arc was progressing. Nicole had been dating Santi, a friend she had met in high school, through their respective college and early career experiences. Now they were both in New York, they had gotten married, and they wanted children.

At first Nicole just figured she’d do what almost everyone in her position does: keep working.

I really, really, really loved being a VC. It is just super fun. It's being knee deep in a ton of research with a ton of people who are so much smarter than you, and they're telling you about what they do. It's very exhilarating, very people driven. So I really wanted to keep doing it.

But, on further reflection—and in conversation with Santi, who was open to a big family pivot—she changed her mind.

I had the realization that both of these things were going to require a lot of time for me. VC kind of necessarily expects you to be the person who can be on call for a founder at least some amount of the time, and I also would probably be that person for my son. I could take a step back [rather than quit altogether], but it would just look like a very different thing. And it had been a few years of 80 plus hour work weeks.

And the realization kind of hit me, and Santi was like, “Okay, that’s what you want? Awesome. We'll try that.”

The big, sudden change was dizzying at first. But the level of grace and intentionality with which Nicole stepped into her new homemaker role was characteristic of the rest of her life. She first had to figure out the footwork from scratch. “My mom worked for the majority if not all of my childhood, so being a stay-at-home mom or homemaker wasn't something I'd considered,” she told me. “I was like: ‘I guess I'm here now. What does that mean? Is this something I can get good at? I guess so?’”

Nicole found continuity through the change. “Your identity shifts so intensely, but you can also redirect the skills that you have.” Initially she felt like she was spinning her wheels, but then she took up “investing in these skills of motherhood,” as she put it.

What does it look like to be good at this? It's not really something again, weirdly, that I'd ever thought about before…. What are my priorities? What are my values? What do I care about in forming [my son]?

It wasn’t easy for Nicole to figure out. “In New York, it was especially hard to find older people who had kids and could act as mentors. Not just people who are my age, but somebody who has raised a few kids and has some time under their belt and is less in the same stage of like, ‘Oh my gosh, this is overwhelming,’ and more like, ‘Okay, but it will all turn out fine.’”

But she did figure it out, and she recognized that this dance had a familiar beat:

There were parts of it that reminded me of startup world and tech world. “How do we take control of this problem with whatever resources we have? It's changing shape all the time. What's a typical way to solve the problem, or to get better at solving the problem, and develop systems around doing that.”

Part of it was finding structure for our days and trying to really stick to that. Part of it was trying to tease out my own priorities, which were things like finding ways for both of us to be outdoors together, finding both of us to have a really rich social community. What are the weird ways I can take advantage of this time in my life where I have a lot of time and a lot of flexibility, where he’s a big commitment, but it’s in spurts and stops.

Nicole started volunteering to help the homeless at a church at the end of her street. She worked at their social services desk, aiding individuals with benefits issues, entering rehab, finding housing, and general tech support. They were happy to show her the ropes and did not mind that her 2-year-old son tagged along. Even more wonderfully, the church served as a large indoor play space for her son while she worked, and much of the population that came through did not get to see many young kids and really enjoyed playing with him.

Nicole wanted to bring together different bits of competence from her community, so she started handing out “mom business cards” to people in her neighborhood who did things that might be of personal or community interest. She started “pitching” them and “tracking” them.

New Yorkers are funny because they're not necessarily super friendly. But I feel like when you make a weirdly specific pitch, they're very open to it. So sometimes you put out the conversational feelers, or even if you meet a mom—I do the thing, which I totally did during VC, which is just a ton of social management. I find somebody, I get their name, I put in two details about their life story. I do a ton of internet research, and then I'm like, oh, interesting. You expressed an interest in running, maybe we go running together in the neighborhood. Or, our kids should have a Spanish speaking playdate sometime. Or, could I use your backyard playspace occasionally for my son and I'll bring you some baked goods? Or, would you be open to giving four 3-year-olds a tour of your seltzer factory? Or, if I bring back 6 friends to your business, will you give us a discounted rate? But sometimes it's also just making a point to inquire after someone's health, or their trip, or if they need pet sitting.

I've talked about this on Twitter a little bit, but I keep my neighborhood CRM in Apple Notes. It’s my relationship management software. I just put the notes from everybody that I meet. Like, the block association president told me, “If you ever need real estate in the neighborhood for something, let me know.”

This is coupled with a great deal of active hosting, bringing into her home the kind of environment she wants for her family.

Looking ahead to the future, Nicole is already mentally choreographing her next big act, which centers on creating an excellent homeschool community for her kids:

I definitely aspire to some version of homeschooling like that, which is just employing all the fun and lovely and complex personalities of New York (or maybe not New York in five years), but pulling them into teaching with communities of families that we really love and enjoy spending time with.

She even mentioned getting some inspiration from her mother-in-law’s homeschooling methods, including an illustrative anecdote (relayed in a recent podcast interview) where dance literally became part of the curriculum:

I think he had originally been doing yard work for them, but they just got caught

up chatting. He's like, I also instruct salsa. So they move all the furniture to the side, and they pay him to teach a lesson.

Talking to Nicole, it is apparent how meaningful all of this is to her—how she’s linked it up to patterns of thought and values from across her life. The networking and social engineering, from Twitter through to VC, the scrappiness of how she built an educational community for herself as she is now starting to do for her son and for others—all of these moves connect into one flowing, magnificent, highly intentional dance. That dance is the embodiment of “the life of the mind,” realized in the singular personality and joyfully hyperconnected world of Nicole Ruiz.