Startup founders have infamously unpredictable daily schedules as they work to establish and grow their businesses. What does such an entrepreneur’s weekly, daily, or even hourly routine look like when sometimes there aren’t enough hours in a day? In the Startup Diaries, founders walk us through a week in their lives and show what it really takes to get a fledgling business off the ground.
When Eiko Nakazawa became a mother three years ago, one piece of early-childhood development research stuck with her: “I learned that 90 percent of the brain develops in the first five years of life,” she says. “Which is quite scary, because most of that time I won’t be spending with my son.”
At the time, she was working long hours at a startup and was dissatisfied with the childcare options she was finding (“quality was a huge issue,” she says). So she decided to scrap her initial business idea and create a solution for her newly-discovered problem instead: Dearest, a service that matches families with qualified educators. Think: babysitters with a curriculum.
At first, the company offered on-demand, one-on-one pairings. “But I realized that it’s really hard to cover the operational cost just with the value proposition of matching,” Nakazawa, a WeWork Labs member at WeWork 175 Varick St in New York City, says. Besides, parent feedback showed they cared more about the Dearest experience than they did its on-demand convenience. “They wanted continuity,” Nakazawa says.
So seven months ago she pivoted to develop small, semester-long group classes run by educators (mostly grad students and retired teachers) and hosted by parents, who open their homes for the weekly sessions but aren’t required to be present for them—it’s group childcare and education in one. She also set her sights on B2B opportunities, launching partnerships with companies like Equinox and fitness and wellness center Mercedes Club. “Members come, work out, drop their kids off, and instead of the kids just sitting in a play space, they can actually learn something—Mandarin, creative arts.”
The shift has benefited the company, which has four full-time employees and two interns: In the past three months, it’s achieved 39 percent growth month-over-month. “We’re very numbers driven,” Nakazawa says. Her goal? “Keep growing!” Below, a recap of a recent work week.
Monday
6 a.m. Go to a coffee shop near my home on the Upper East Side to organize my priorities and tasks for the week. I use a simple, unlined journal and a version of the Eisenhower Matrix.
8 a.m. Wake up my 3-year-old son while my husband leaves for work.
8:10 a.m. Breakfast with my son. We each have a bagel and a glass of my husband’s homemade green juice.
8:30 a.m. Welcome my son’s friends and Dearest educator for their School Readiness Program. My son is starting pre-K in September, so we’re preparing him for that.
9:15 a.m. At my WeWork desk. Review high-priority tasks and answer emails that require a quick response.
10 a.m Weekly team stand-up. Review last week’s achievements and this week’s goals.
10:30 a.m Meet with marketing team to go over the week’s digital marketing plan, including social posts and blog posts, and our latest article on summer learning loss.
11:30 a.m. Prepare for a meeting with Marie Kondo with our head of marketing, Brittne, and chief learning officer (CLO), Jessica (we were connected through a mutual investor). We’re discussing ways to bring her “spark joy” concept to little kids—she wants our thoughts on activities and learning materials.
1 p.m. Leftover Thai food for lunch.
1:15 p.m. Review the layout change of our landing page with our tech lead. Discuss findings from Google analytics, FullStory, and in-person user testing to plan further UX changes.
2:30 p.m. Work on Y Combinator application with Jessica and incorporate feedback from other YC-funded companies. One note we’ve consistently gotten is that we have to be more concise. For every question, there’s one point we need to get across—not 20. Jess and I work on this nonstop into the night. But we eat and snack, and at one point my husband calls because my son wants to talk to me. We chat a little bit and say goodnight.
11 p.m. Submit the YC application and take an Uber home.
Tuesday
8:30 a.m. Welcome my son’s friends and educator. Today’s session is on mindfulness art.
8:50 a.m. Go directly to a client’s home where a new Dearest program trial is taking place. The parents who end up choosing us are really engaged in their child’s development. People think kids can grow up climbing trees and playing with sand, and that’s true, but there are certain things you can do to promote their development even further.
11 a.m. Speak with our insurance broker about additional coverage needed for our corporate partnerships.
12 p.m. Lunch with a former colleague who’s visiting from Japan. We grab pasta at Pepe Rosso to Go, a tiny Italian joint near the office.
1:30 p.m. Meet with the WeWork HQ community team to discuss “Take Your Kids to Work Day.” Today we discuss activities that promote innovation, problem solving, and creativity; scope of work; and budget.
2:30 p.m. Meet with Jessica and Brittne to discuss the WeWork project: programming, list of educators to hire, and logistics.
4 p.m. Coffee with one of our angel investors, Adrian, who’s been with us from the beginning.
4:30 p.m. Meet with business-development intern to discuss B2B-outreach strategy. We want to work with more luxury-rental buildings. These buildings want to differentiate themselves, and our service is a great luxury amenity for the residents.
5 p.m. Zoom call with a venture capitalist. Review the spreadsheet he uses to calculate a company’s total addressable market (TAM) and input the numbers for our next meeting. This is a series B VC, so he won’t invest in us yet, but he wants to see how we’re doing, and it’s helpful to get his resources and advice.
5:30 p.m. Send emails and finish high-priority tasks.
6:15 p.m. Head home early. (I’m usually home at around 8.) Spend time with my family.
8 p.m. Test activities for the KonMari project with my son. He is a guinea pig for Dearest. We test a lot of activities on him. In this case, he got distracted and was playing with his train.
Wednesday
9:30 a.m. In the office, reviewing goals and tasks for the week.
11 a.m. Head to a meeting with a luxury-rental building we’re about to launch with.
1 p.m. Quick bite in Midtown.
2:15 p.m. Check the tech team’s bug fixes and the improved filtering function on our marketplace (where parents can search for open groups). Approve the push.
2:45 p.m. Provide feedback on a business proposal we’re going to submit to a wellness company we’ve been chatting with.
4 p.m. Review curriculum content submitted by the team.
5 p.m. Brainstorm with the team on how to minimize last-minute educator cancellations. Our new plan includes cancellation jars: We’ll collect fines, and the money will go toward community events.
7 p.m. Order groceries through Foodkick.
8 p.m. Skype call with our angel investor in Japan. He has funded and built highly successful companies there.
9 p.m. Head home, read to my son, and tuck him in. My husband does a lot. He finishes work early and he’s very involved. Without him, work would be very difficult.
Thursday
9 a.m. Go directly to NYU StartEd, an incubator program we were recently accepted into.
10:30 a.m. Back in the office.
3 p.m. Meet with Mercedes Club about our new partnership.
4-6:30 p.m. Administrative work: Check reports submitted by educators, review feedback and Net Promoter Scores (NPS) from parents, process payments, analyze growth model, input profit and loss.
7 p.m. Drinks with fellow Japanese female founders. Although there aren’t many of us out there, we get together once in a while to share some stories and drink some wine. Members include Rie, who runs fashion-tech company Material World; Saya, of the sandal brand SandbySaya; and Fuko, of art direction and marketing company 3 DAY MONK.
Friday
8:30 a.m Arrive at Pre-series A offsite in Brooklyn. The event, which includes a day of learning from founders and investors, was organized by Charlie O’Donnell, a partner at Brooklyn Bridge Ventures, who I met through another VC. (I recommend all startup founders read Charlie’s blog.)
9-10:15 a.m. Attend the first panel of the day, “Getting to a Series A.” We’re in our seed round, but it’s helpful to know what to expect down the road. It’s eye-opening to hear how VCs choose who to fund, and even though it’s easy to drown in the daily work, I need to make this time and effort to connect with other founders and investors.
2:30-3:15 p.m. Attend a memorable breakout session with Anthony Casalena, the founder of Squarespace. He built a profitable business without major funding, so it’s refreshing to hear his point of view.
6 p.m. Meet with Marie Kondo and her husband, Takumi (the CEO of KonMari Media), at Harvard Club to discuss the spark-joy project. I’ve read her book and watched her Netflix show, so I’m excited to meet her. She turns out to be graceful and petite—just how I imagined she would be in person. We bond over how learning has to be fun, especially for the little ones, and I find out how she and her husband met—on an elevator! She has such a unique vibe, and her husband is witty, sharp, and a great storyteller.
8 p.m. Get home. Eat dinner with family, and promise my son I’ll take him for rides on the L, G, and Q trains (his current obsession) this weekend.
Prior to the startup life, I worked long hours, but I was able to switch off once in a while. With Dearest, I’m on all the time. Bookings happen on Sundays, the system shows bugs at midnight, and so on. The more invested you are in a business, the more personal work gets. Every rejection and every failure hurts. But my colleagues and I believe in the power of early childhood education and the impact that we can make in the childcare world. There is no better feeling than reading a great learning report submitted by an educator or a mom’s post on Facebook, sharing how our service helped her get back to pursuing her passion again. This makes everything worth it.
