Authentically Imperfect | Ann Crady Weiss

Authentically Imperfect | Ann Crady Weiss

Meet Ann Crady Weiss. Actually, you may already know her. Perhaps your baby sleeps every night to the gentle white noise of the Hatch Baby Rest, from a company she co-founded with her husband, Dave Weiss. Or maybe you were active on Maya’s Mom, a social networking site for parents that Ann created in 2005 and successfully sold to Johnson and Johnson. It’s also possible you recognize Ann from her dramatic performance on Shark Tank, where she became the first ever pitcher to convince a shark to invest after she’d already been told no.

Regardless of whether you’ve met, Ann’s warmth and honesty make you instantly feel like old friends. Having a coffee with Ann is like sitting down with your girlfriend, sister, and career coach simultaneously. She pulls no punches with her questions and perspectives, but she’s also the first to champion others’ triumphs. As a two-time startup founder, part-time venture capitalist, and mom of three (Maya, 15; Derick, 12; and Ben, 5.5), Ann’s no stranger to the hard work of charting one’s own path and building community along the way.

What were you doing (professionally) before your kids were born?

I was at Yahoo back in the day, though, in some ways, I had always been an entrepreneur. There’ve been several very successful entrepreneurs in my family who inspired me. I had something to prove to myself, too, so I founded a company that I personally felt passionate about. Maya’s Mom was intended to be a better version of Yahoo Groups and MySpace, back when there weren’t online spaces for parents to support one another.

Did you think about changing directions, scaling back, or quitting when you became a mom?

I knew I was happiest as a working mom, but I really knew that I wanted to do something that had a ton of meaning, which led me to found Maya’s Mom.

After I sold Maya’s Mom, I took three years out of the workforce when my oldest kids were 5 and 7. I really wanted more time with them. However, it was a difficult decision because my identity was wrapped up in my professional story. I was worried people would perceive me differently. I’d be at a party and feel the pressure when people asked what I was doing. I’d smile and say ‘Nothing! I’m a mom!’ but it felt a little off.

What kind of headwinds did you endure as a working mom entrepreneur?

I certainly knew I was in the minority, but didn’t have overt experiences. I was in the lucky position of having a strong network of Yahoo execs to advise and invest when I started Maya’s Mom. That’s a piece of advice I give to everyone: do a good job, whatever you’re doing.

Some investors didn’t get the parenting space. “Moms do not have time for social networking,” one told me. But I believed in the vision and developed a thick skin to push it forward.

One of the things that I wrongly assumed was that my schedule would be flexible and I’d have more time. But as soon as you raise venture money, you’re on a clock. I put a lot of pressure on myself, working more than I planned to. But I enjoyed it; I was really filled up.

Ann at work testing the Hatch Baby Rest.

How has motherhood influenced the way you lead?

I’m not sure this is all attributed to motherhood, but after I sold Maya’s Mom, I went through a divorce. My ex-husband is a great guy. But I realized that I had lived for 30 years checking boxes instead of focusing on what was right for me. I wanted to create a life of authenticity as an example for my kids. I did a lot of work on myself, exploring the angst inside of me in order to give my kids a different perspective.

One result of this self work is that my leadership style has changed. I used to be loud and opinionated -- a bull in a china shop. But I’ve realized this style didn’t make me feel good and it wasn’t effective either. Now I see that it’s sometimes harder, or at least less efficient, to have three meetings to get to a decision, but the process is way more fruitful in the long run.

What has surprised you about motherhood?

Before I had kids, I thought I had a lot of power to shape them. Now I see that although I have influence around the edges, they are who they are.

Case in point: when my daughter was in preschool, I watched another kid rip her art project right out of her hands. I felt rage inside of me. I wanted her to react like I would and stand up for herself. But my daughter -- who is careful and patient -- didn’t really care about it. It wasn’t important to her and she didn’t react.

It’s a constant balance for me between projecting my own feelings on my kids and being sensitive to theirs. It’s hard.

How about a recent proud mom moment?

Recently, my son’s 6th grade teacher told me that she had asked the class to divide into groups. They all quickly formed into little pods, including my son, except for two kids who were left out. Derick noticed them and, without prompting, left his group to create a new one with them. I’m really proud of this moment.

What lessons do you want to pass to your kids?

Authenticity. I did a lot of work to figure out who I really was and what really made me happy. I hope they can do that a lot sooner. Self awareness really matters.

Any advice for tending to a relationship amidst a busy career and child-rearing?

Young kids are very hard. There’s well documented research that shows marital satisfaction plummets with kids. Recognize it. A relationship needs to be tended to. Being a mother is so wonderful, but being a partner is, too. Respect the primacy of that. My husband and I work together at Hatch Baby every day, but we also prioritize date nights, workshops and therapy sessions to connect with one another. It’s so important.

Being a new parent throws your whole world upside down. We've lived it! At Hatch Baby, we're always trying to create new ways for parents to get the support they need, whether it's caring for their babies or themselves, at the most basic level. The product we're getting ready to launch, an app called Answered, I think will really help parents get the expert help and support they need raising kids. We're so excited about it.

What do you tell women who are coming up behind you?

There absolutely is gender bias and, for the most part, it’s unconscious, but it’s definitely there. Don’t let that get in the way. Don’t get in your own way. When you pitch your company, be a freakin’ badass and sell it.

It’s clear that Ann’s generosity of spirit and drive are two complementary traits that propel her success at home and at work. Yet, when we asked what makes her boss, Ann humbly pointed to her own imperfections, recognizing that these flaws give her license to be forgiving of others, too. It’s Ann’s authentically imperfect approach to balancing her family and career that we think is totally boss.

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