LESLIE BORRELL | FOUNDER, CAREFULLY
"I love to see ideas come to life, and having it be my own makes it even more exciting."
How do you start your day?
I make breakfast for my son, drink coffee, and go for a walk in the park.
What would you tell yourself as a teenager?
I probably wouldn’t listen to any advice. I think I’d like to just hang out with myself as a teenager in the 90s and remember what it was like to live in our world back then when things seemed a lot simpler.
What is the best piece of advice you have ever received?
What got you here won’t get you there.
What do you need to get you through each day?
A checklist makes me feel more productive, an updated calendar keeps me on track, a deadline keeps me motivated, and users inspire me.
What are you reading?
I just downloaded The Power, but haven’t started it yet. My interest in the book was triggered by a conversation about the recent controversy at The Wing and Crisis Text Line. We were discussing how power corrupts. I’m reluctantly looking forward to reading this after it was quoted by several people in the conversation.
Briefly describe your business and inspiration for it.
Carefully is a mobile platform for busy parents to create private trusted networks with people they know to share care and organize playdates. We provide a way for busy parents to connect with their communities so they can support each other with childcare as an alternative to paid for care while giving their kids a playdate. Integrated with parents’ calendars, maps and customized availability settings, we make it easy for you to find playdates when and where you need them and stay updated with notifications and in-app messaging. We work on a system of karma care hours that can be earned and redeemed to keep everyone in balance while providing free virtual events, offers, and discounts from small businesses and individuals to support you and your family.
As a single mom in NYC, I was originally inspired to build Carefully when my son was three and he had started preschool. I was ecstatic that he was old enough to start having real playdates with other kids where he would be happily occupied with his playmate and I might be able to relax for a minute. However, I quickly learned that inviting kids for playdates also meant entertaining their parents. While it’s great to connect with parents, as an introverted mom, I find entertaining at times. I wondered how I could make it more acceptable for parents to drop-off their kids for playdates. When recounting my personal experience to others, they often respond with emphatic nods of agreement and laughter from shared experiences.
What made you decide to become an entrepreneur?
I had been wanting to move out of my VP of Engineering role for a while, eager to build new skills and showcase my ability to work beyond a pure engineering role. I had held that role, and others like it, at several companies including Intersection, Amplify Education, Etsy, Travelocity, and Thoughtworks. I was burned out from the corporate job, the industry, and the politics, and that’s what prompted me to develop Carefully four years ago.
What was the tipping point for realizing you had a good business?
Working in software development, I love to see ideas come to life, and having it be my own idea makes it even more exciting. With Covid, childcare has come into the spotlight and has given Carefully the opportunity to help in so many fundamental ways that provide solutions to widespread childcare problems. We need community, we need trusted networks, and we need affordable options for childcare more than ever. These are the fundamental elements of Carefully.
What would you have done differently in your start-up journey?
I started Carefully in 2016 and released it on the app store in 2017. I wish I had spent more time and effort building the brand/community. I would likely be in a different place today if I had started some of the social media and community-building efforts earlier.
When self-doubt hits, what do you do?
Two things help me - First, talking to my co-founder, Jamie, is my safety net. Usually saying things out loud makes the idea seem less scary. He helps me break ideas down to the details. He also helps me identify and contend with my fears. Secondly, knowledge is power. When I’m feeling insecure, alone, or doubtful of myself or my abilities, I look to online communities and articles to learn and understand the thoughts from people I respect. I generally learn that other people are going through similar situations and can help stimulate thought and share their experiences and learnings. Also, just knowing that I’m not alone in my fear and self doubt is often enough to get out of that downward spiral.
What aspects of being an entrepreneur do you love and/or dislike?
I don’t like being in the spotlight and having to “sell” myself. I’m used to working behind the scenes, so learning to pitch a product/service and even myself as a Founder is uncomfortable. On the other hand, I like being in control of my own destiny and being able to make decisions without having to go through a whole hierarchy. Learning how to manage that discomfort is worth it (and something I’m actively working through). You make mistakes but you can own them and move on.
Are there any go-to resources that you have found useful to run your business?
Slack (for communication), Firebase (for app analytics), and Slite (for documentation).
How did your experiences in the corporate world prepare you for entrepreneurship, or not?
The biggest skills/talents that I think are critical to starting a business and leading software teams are building great teams, understanding people, dealing with ambiguity, agility, and building products. Of course there are a whole bunch of other skills I don’t have that I’m learning as I go!
What would you say to another woman who asked you if they should take the leap and start their own business?
Let me know how I can help because getting started is sometimes the hardest part. Once you start, you will know if it feels right.