Yin Li is founder of NurtureList–an Airbnb-style platform for connecting parents with daycares and preschools. Gone are the days of tracking down disparate pieces of information through word of mouth! With NurtureList, parents can efficiently evaluate a manageable number of options.NurtureList centralizes pertinent information–such as the curriculum, admissions guidelines, policies, hours, available spots, and tuition–describes the activities that kids can be expected to participate in, and provides photographs of the facilities for preschools and daycares in your neighborhood. Recently, NurtureList also began to offer Parent Perspectives, where parents whose children have attended the schools can share their experiences online. Yin started NurtureList when she realized that parents were spending a lot of time researching daycares and preschools and that the primary methods of gathering information were unsatisfactory. She spoke with me over tea in her garden about the pull of the role of CEO, the existential weight of starting a business, and the satisfaction that results from pursuing work that you are truly excited to do.

After college, Yin faced two major decisions. The first, was settling on a field to pursue (her fervor for her initial interest, International Relations, was doused after a summer spent coding the tax consequences of European Union votes). After cycling through a variety of jobs, she latched onto a new vision while working as an investor in a private equity firm. Often serving as the right hand woman at board meetings, Yin had the opportunity to observe CEOs at close range, and realized that she wanted their job. Why? According to Yin, “it’s the mix of the strategic decisions that you have to make, with great responsibility for your employees, your company, and your investors. No other person in a company has that – it’s like steering a big ship. You are deciding where the ship should go–looking out ahead–but at the same time, you are responsible for everyone’s well being.”

The second major decision Yin faced was which project to pursue after business school. Although several options presented themselves to Yin, nothing wholly grabbed her. “I had done two research projects into two potential startup ideas in business software, and I felt that I had found a way to make money, an interesting product I could build. But the ‘why me, why now?’ wasn’t clear to me.” For Yin, the project had to meet two criteria: “I was looking for the intersection of two things: A good business idea that was emotionally interesting to me.” Then, while taking a course called Work and Family, she learned that many of the alumni of her business school were spending large quantities of time sorting out the logistics of childcare. Further research revealed that the brick and mortar childcare industry (better known as daycares and preschools) was woefully behind the technology curve. “Parents had such a hard time finding out which daycares fit their schedules, had spots open, and otherwise matched the family’s preferences. I learned that some parents in Oakland actually went to local agencies in person in order to print out a list of providers in their city because the information was not available online. I didn’t expect that in the Bay Area.” After numerous parent interviews, she was astonished to confirm that what she had heard was true. That is when she got the idea to start NurtureList.

According to Yin, what helped her navigate both decisions, was some sage advice from a friend several years ago. “My friend Margaret was thinking about whether to pursue a professional degree. It was going to be something that she would have to put a lot of time into and she would have to make a huge investment in her personal life. We were discussing it, and she said something like, ‘well, I always thought that if I really wanted to do something, I would make time for it. If I really wanted to do something, it should be really obvious to me.’ That was a big light bulb moment. That is the lens through which I have put almost all of my decisions. For example, when I was at Stanford in my MBA, and I was looking at all these ideas that were in enterprise software, that were interesting opportunities, but I didn’t really feel excited to move forward, I just remembered my friend’s advice and felt like it wasn’t right to start a company in something that I wasn’t truly gung ho about. And maybe that was something that I knew intuitively when I decided not to pursue an academic life. Now I use that lens to evaluate ‘should I go get a regular job at a bigger company, and have more normal employment?’ I could do it, but would I be excited to do it?”

What Yin is excited to do is learn new things, something that occurs constantly when working for a startup. “I think a lot of what excites me is learning something new, which is practically all the time at a startup. Therefore I feel like I’m doing the right thing. I may feel like I’m banging my head against the wall, but I am learning something new, and that makes me think that it is worth it to go on this journey.”

One major lesson she has learned so far is the value of relying on others for help.“I’m going to friends and mentors and advisors 100x what I’ve done in the past. Almost everything I do, I need to ask somebody for help, because I’m a new founder. Every introduction, every question I have, I need to lean on other people. And so that’s a new experience for me. Because I’ve never been in a job before where pretty much everyday I’m asking someone to do me a favor. So much of my success depends on rallying the people around me.”

She has also learned that starting a business comes with a heavier than expected psychological weight. “Starting a company is a lot darker of an experience than I thought it would be psychologically. Because of this feeling of ‘am I doing something that’s really impactful or useful to people?’ Before you start a company, you might think that designing and building a product that is actually helpful to folks is a fun and primarily intellectual experience. You expect hardship, but only in the sense of not earning a salary and maybe having to eat ramen. But in reality, it is a much more existential experience, and your greatest challenge is, ‘am I spending my life on the right thing?’”

The jury is still out on that question, as well as the question of whether this type of work is the best fit for her, says Yin. “All the tasks that you do early on in your career are really execution focused. You’re not the captain of the ship. You’re not responsible for people, and so I’ve never tested the skills I’m having to develop now. I’m only thinking they are a fit for me because I aspire to be that person, not because I am actually good at any of those things. That is the question to be answered. And I am open to the fact that maybe I’m not that person. There’s a lot of stress involved in being that person, and maybe I’m much better being the second person or a supporting role. I don’t know yet.”

What is certain is that the job is fulfilling. Says Yin, “I’ve heard from a daycare provider that we’ve made their lives a lot easier, and connected them to parents, giving them almost a home online, where they can show off why they’re good. That has been really rewarding for me because childcare is a somewhat stigmatized profession. There’s something really rewarding about allowing someone who takes pride in caring for kids to professionalize themselves and turn what they’re doing into a respected business. I now feel extremely rewarded whenever I meet one of those providers, who takes a lot of time to build a very thoughtful profile and show off ‘this is how I believe kids should be raised, these are my values, this is what I do, this is my program. I take the kids to the park 5X a day, or on field trips every week.’ I would love to see childcare become a professionalized industry, while still maintaining all the warmth and love and special touches. It’s so nice to see a provider get the recognition that they deserve.”

When Yin does experience doubts, she relies upon two major strategies to assuage them:

“First, I get support from friends. I think that’s really important for putting your doubts in perspective. My friends help me realize that anyone has challenges at work, and so there are going to be challenges at a startup. Second, I get really analytical about my concern and try to think about the results that I’m seeing in the business. I think, ‘what is it exactly that I’m worried about? Is it normal? Is it expected? Or does it actually say something really bad or really good?’ I try to think about it from a business perspective.”

She is also comforted by the fact that she will still learn from the experience, and perhaps even gain a new appreciation, even if the venture does not pan out. “If the startup doesn’t work out I think that I am going to be grateful to have a regular job again, because this has given me an appreciation for the benefits of going to work at a real company: Having teammates, having support, having well-defined goals and customers. If nothing else, it will have given me an appreciation for the other path.”

Her hope for the future of NurtureList? “That a lot of parents and owners and admissions directors use it, and it becomes this living community for under age 5 care. So it’s not just a business listing, but it’s a place to find all sorts of insightful information that you want as a parent, and also as a way for the providers to learn about how they’re impacting their communities.”

Thank you, Yin for sharing your inside perspective on building a business from the ground up. Your determination, strength, and clarity of vision is inspiring. Here’s to the realization of your dream and the continued growth of NurtureList!

For more interviews with women who are forging their own paths, career and otherwise: Follow me on twitter @shespoised or like She’s Poised on Facebook (and select Get Notifications from the drop down menu).