Meet Fearless Female: Lynn Perkins

The moment you meet Lynn, you just want to give her a hug. She is welcoming, down-to-earth, and has a contagious smile that lights up a room. But don’t let her easy, calm persona fool you: Lynn is fueled with a fearless tenacity to achieve great things and make every moment count.

Whether running the company she founded, UrbanSitter, or savoring time with her friends and family, Lynn, a self-proclaimed “work in progress,” seems to do it all with grace. We sat down with her to learn her secrets to keeping it cool, letting go, and the magic of outsourcing. Here is her story.

Why did you found UrbanSitter?

I love setting people up – whether finding new dates, new restaurants, or introducing you to someone in a new city, I love connecting people. When my twins were 2 years old, I took some time off of work and happened to start connecting all my friends with nannies and babysitters. People kept saying, “Since you’re another mom in my pre-school, I trust your recommendation.”

So, it started to dawn on me: for parents, the idea that being connected to somebody who knew the sitter created a lot of trust. UrbanSitter taps into a parent’s personal networks to connect them with sitters of friends, moms groups, and parents at their kid’s school. For sitters, having everything in one app, and not having to take phone calls to book jobs was a game-changer. UrbanSitter was a solution that worked for both babysitters and parents.

What pushed you to finally do it?

My background is in start-ups, I had done three before UrbanSitter. I started telling my friend who is an engineer about the idea. He recently had a babysitter cancel on him, and he said, “I can build this!” And then we were off and running. We didn’t have big plans to launch a company. The more I circulated the idea, the more people liked it, and then I spoke to some babysitters, and they really liked it. So, I figured, let’s give it a shot, launch locally, and if it is well received, we can grow it.

I have bounced around between big and small companies throughout my career – I wasn’t worried about job stability for myself. When you take other people along for the ride, and their well-being is in your hands, that is when it starts getting harder.

What has been the hardest thing about building UrbanSitter?

The hardest thing about building any company is knowing in your head where you want the business to go, versus where you actually are today, and knowing how to get the resources rallied to take it to the next level. There is always more you want to be doing, and it never happens fast enough.

You have a big job and 3 kids – how do you prioritize and let go?

I prioritize engaged time with my kids over making things for them. For instance, tomorrow is my twins’ birthday party, and while I love the idea of baking a cake with nice decorations, I just don’t have the capacity for it. Instead, I am going to my kindergartener’s end of year picnic today. For me, it is a time versus experience tradeoff. For example, I will outsource buying kids’ clothes to my nanny, so I can go to the park with my kids instead. I try to outsource when I can.

I also always schedule time for working out. I prioritize exercise because I find that one hour makes me more productive for the rest of the day. One thing I am prioritizing right now for this summer, is not taking any outside meetings. This is a tough one for me because I love connecting with people and especially supporting female founders. I am saying “no” for the summer, so I have time for my team at work, and my family.

What else do you do for fun to recharge?

For me, it is being outside: skiing, going to the pool with my kids, or hiking. I am indoors all week, so being outside is such a relief for me. Outside also means getting away from electronics. If we are out on a bike ride, or picnicking somewhere, it is harder to get pulled back into the day-to-day work stuff.

"I don’t take things personally. I take the feedback, think about what I can use, and then move on. There are battles you can win and battles you can’t."

Tell me about times when you felt defeated, and how you kept going.

We have had our fair share of investor meetings or board meetings that haven’t gone well, or I’ll tell someone about UrbanSitter, and they say they would never use it.

When it’s poor customer feedback, I’m motivated to do a better job. If it’s a meeting that just doesn’t click, and I know the reason is a lack of understanding about how massive the child care dilemma is for families--it motivates me to go back and work even harder.

Plus, I don’t take things personally. I take the feedback, think about what I can use, and then move on. There are battles you can win and battles you can’t. It’s not worth my time to convince an investor that child care is a huge opportunity. I go back to focusing on the positive. There are some parents out there who love our service, and it has made their day. So, the secret is to refocus on the positive.

Tell me about a time when you didn’t fit in, and how you reconciled that feeling.

The very first year we raised money, one of our investors had an event, and I was one of two females there. At the end, they had a whiskey-tasting, and I can’t remember if I was pregnant or just didn’t want to taste whiskey, but in that moment, they were all going to do this thing, and I felt left out. The other woman turned to me and said, “Do you want to go upstairs and get french fries and dessert?” I said, ”absolutely.”

On the personal side, there is an interesting thing happening in our culture where there is a divide between working moms and non-working moms. There have been a few times when I was at a playdate or event, and I found that the non-working moms seemed much closer to each other, and I felt left out for not being as close with them. It’s interesting, when I talk to the moms one-on-one, they feel similarly alienated when it comes to groups of working moms. It is such a shame, because we are all just trying to get by.

How do you start your day?

My husband works early hours, so I am always the morning person at home for school duties. It is the most structured part of my day: getting the kids out the door.

The one thing I do for myself in the morning is 5-minute journaling. It helps me set my intentions for the day: two things you are grateful for, and three things that would make today a good day. Before I get interrupted by anything else for the day, I write down my top priorities, either work or personal I like it because it enables me to set my intentions before the fire drills start.

What keeps you up at night?

Logistics. Like, “did I forget to bring the stuffed rhino back to the kindergarten class?” I usually just write down what I am thinking about, and then I go back to sleep. But, if I can’t, I listen to this app called Calm that tells stories that are super boring, and that puts me back to sleep in 4 minutes.

What is something you are really excited about right now that is on the horizon?

My kids are finally at an age when we can start doing bigger trips and they are soaking everything in. We are in a short 3-year window where my oldest kids still want to spend time with us, and the youngest can go to older kid activities. I am excited for this time when we can travel to cool places and enjoy our time together.

If you had one piece of advice that you want your kids to never forget, what would it be?

Take advantage of opportunities when they arise. I set out on a path and I haven’t stuck to that path, but it has made me better. When something looks interesting, take a shot at it.

Figure out what it is that you’re passionate about, put your energy behind it, and things will work out.

Lynn's Picks

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The Tee

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