Mama Shaker: Jess, Building Relationships Around Experiences We Share

Jessica Gupta felt isolated as the first of her friends to get pregnant, before she knew that motherhood would bond her to women she barely knew.

“I thought that what I was going through emotionally and physically was something other people couldn’t understand completely,” she says.

And even if friends do have kids, it can be hard for them to remember all of the minutiae that occurs weekly and monthly as your body and your baby grow.

“When I was pregnant, I was connected to two women that were due at the same time as me,” she says. “We started chatting and the relationship grew. I kid you not, there were days when we would probably send over 50 text messages between the three of us.”

Jess and her new cross-country confidantes supported each other through the physical and emotional changes that carried them well into motherhood.

“I think what’s really special is they were the first people I told when I went into labor,” she says. “They were the first people I really reached out to because they had been with me through it all.”

The experience inspired Jess to create Taavi, an abbreviation of “it takes a village,” to match together moms-to-be from all walks of life.

“Getting out of the house can be tough,” she learned after the birth of her daughter. “It’s really intimidating to put on clothes and do your hair and go meet other mothers.”

“What I wanted to create for women was a support system because that’s what I had created for myself,” says Jess, noting the importance of doing so before baby, when you have the “mind space” to “focus on building strong bonds as women first.”

Sharing a similar mindset with her co-founder, Renee, was also helpful in creating a partnership in the early days of Taavi.

“When I met her, we had this really natural connection of ‘hey, we want to honor women during pregnancy,’ to focus on the woman, not just the mom,” she says.

“It’s been a really awesome relationship because we’re both mothers, we both had different experiences in our pregnancy and so we can speak from different vantage points,” she says. “At the same time, we believe in this immense need for community for moms and the support that comes from that community.”

While plenty of pregnancy apps and groups provide information about every milestone and symptom, it was important to Jess and Renee to focus on building relationships between mothers.

“The goal is that we’re actually creating dialogue or creating intimate connection through nurturing friendships,” she says.

How this Mompreneur Makes it Work

Just shy of three years into motherhood, Jess has built a relationship with her daughter using a similar support structure—rooted in the routine that toddlers find comforting, which affords a few moments of solace every parent needs.

“There are some routine components that I started to put into place this year, which has been incredibly helpful,” she says. “One of the goals I had this year was to wake up before my daughter and actually shower and be ready.”

Jess also spends a few minutes in the morning alone writing in a journal about the things she’s grateful for and the things she wants to let go. So she’s refreshed and has a cup of coffee in hand by the time her daughter wakes up.

“I have to be that backbone of routine for my daughter too,” she says. “I think that makes her happy and gives her something to look forward to every day.”

“She’s a stickler for plans. I think that’s just part of their age group. They want to know what they can expect.”

Structure also helps Jess balance the less predictable path of running a startup.

“As an entrepreneur, I think the hardest part is not knowing exactly what you should be doing all the time,” she says. “One thing that I’ve been trying to achieve more of is setting weekly goals as opposed to these grandiose quarterly goals.”

Compassion is also key for Jess. When we spoke earlier this year, neither of us knew how timely her words would be, “understanding that I know shit happens, life gets in the way.”

“It’s hard because in the space of creating your own company, you don’t have a boss telling you you’re doing a great job,” she says. “You don’t have traditional reward structures.”

Jess has realized the reward for any of us achievement-oriented mothers comes in the compassion of reminding ourselves and each other “that you’re doing a killer job, even if it doesn’t feel like it.”

“I think the hardest part of motherhood is that as women we forget to take care of ourselves,” she says. “My hope is that Taavi will bring back some of the nourishment that we we don’t get to experience daily.”