The Founder Who Turned Life's Hardest Moments Into Fuel

When I met Mahima Chawla at The Grand Pursuit LA launch event, she shared a story that stopped me cold: her colleague once brought a laptop to her C-section just to apply for leave benefits.

That story sparked the idea for Cocoon, Mahima's company that's now raised over $40 million to fix America's broken leave system.

But here's what really amazed me: While building her startup, Mahima was also navigating divorce, co-parenting a newborn, and recovering from major knee surgery. Most founders would have quit. She turned these challenges into fuel.

Her journey from Bond Street to Block to founding Cocoon proves something we believe deeply: ambitious mothers don't have to choose between career success and family fulfillment.

This is exactly why I'm thrilled to have her leading a roundtable on "Leading Through the Storm: Navigating Company Building During Life's Hardest Moments" at The Grand Pursuit retreat in October.

Here's how she did it, in her own words.

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Tell me about the moment that led to Cocoon.

I was working at Block building small business lending products when my product counsel told me about her "crazy parental leave experience" where she took her laptop to her C-section to apply for her California EDD benefits. That was the first "wait what?!" moment that led to me talking to many people who had taken leave.

I kept hearing stories about how challenging the experience was navigating all of the logistics. I then spoke to employers and heard from 50+ HR leaders that "leave is an absolute nightmare" and "the worst part of HR." I kept wondering why there was no solution people rave about.

After evaluating the market, I realized that no one had solved leave the way I envisioned it. Robust software that took care of the heavy lifting and intuitive design that created an easy experience. I wanted to build the solution that people did rave about, and that's what led to Cocoon.

Your roundtable is called "Leading Through the Storm." You've navigated some serious personal challenges while building Cocoon. What made you brave enough to share this?

I grew up with what I would consider a perfect childhood. A close-knit loving family, and physical, emotional, and financial security. I only realized how unique this was as I got older and people would share their own experiences. I remember in college once saying "I want to give my child the exact childhood I had" and my friends looking at me confused because they all wanted the opposite.

Then came my first real hardship at age 31. Navigating a divorce and co-parenting while raising a newborn while building an early-stage company. It didn't help that I also had a ski accident and tore my ACL, MCL, LCL, and meniscus and had to recover from surgery.

During that period, I experienced emotions at depths I'd never felt before. I also had to figure out how to let go of a vision for my life and family that I'd held onto since I was 5 years old.

The thing that helped me most was talking to people who had experienced similar things. Connecting through shared experiences was such a source of strength. I share openly because I hope it helps someone, even if in a small way, and to remove stigma around things that are just part of life for many people.

While that period was really tough, proving to myself that I can get through A LOT and not just survive it, but really thrive is one of the most powerful and liberating feelings. I live my life authentically in the way that I want to versus how I maybe should, and honestly it makes me a lot less scared of the hard stuff because I know I'll get through anything.

At The Grand Pursuit, we talk about not having to choose between career excellence and family devotion. What does that actually look like in your life?

It's true that you don't have to choose between career success and family fulfillment as a binary, BUT I do believe you have to recognize that you're going to make some trade-offs in both. There is finite time and you have to decide how you're going to spend it.

My daughter is always going to be the #1 priority AND my career is something that gives me a lot of motivation and satisfaction. For me this means thinking really intentionally about how I plan out my days and weeks so I can spend time with my daughter in the ways that are important to both of us, AND achieve what gets me most excited on the career front.

The power of taking the time to plan out your time should not be underestimated!

Beyond CEO, founder, and mom, who are you at your essence?

It's easiest for me to answer this by sharing what I care about most, in order: my community (family/friends), my career (which hopefully involves building many companies!), and learning/seeing new things (exposing myself to new things and exploring the world).

I try to make time for all of these things over the course of a year because they all fill my cup in different ways. Underlying all of this is living a life of peace & joy and so I try to be really intentional with how I spend my time and energy to create that. Not to say that life is peaceful & joyful at all times, but if I feel that way most of the time that's all I really need.

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What strikes me most about Mahima’s journey isn't just her resilience, it's her radical honesty about the trade-offs and her refusal to pretend it's all effortless. This is the kind of conversation that changes how you think about what's possible, and exactly why I can't wait for her to lead our roundtable in October.

— Rei