Dealing with grief as a Founder

Founders deal with grief as part of this masochistic rollercoaster we sign on for when we choose to be entrepreneurs. But oftentimes dealing with it is evidenced in abrupt burn out or depression and anxiety rearing its ugly head. Entrepreneurship and the euphoria of creating something that doesn’t yet exist also has the power to overtake our lives to the detriment of who we are as humans.

Let’s talk about it. Let’s get real with how hard this journey is, especially for women, and honor our humanity.

The day I decided to raise a seed round, I found out I was pregnant. Fast forward nine months and I am bringing my daughter — my first child — into the world the same day my funding round is committed.

My daughter turned one year old yesterday. As I reflect over the last eighteen months, the feelings of grief come flooding back amidst the incredible memories of raising this beautiful girl and somehow still showing up everyday, putting in my heart and soul, in brutal early stage fashion.

Entrepreneurship is a choice. You choose to show up, everyday committed to being bad at many things until you aren’t anymore. To growing and learning, and being the rock of your company. As with anywhere you choose to spend time, that means you are prioritizing that task or meeting above other experiences or roles in your own life.

Enter grief.

For any founder at the seed stage who has institutional capital as part of the round, you know it’s normal to negotiate terms that are agreeable on both sides. But what did that mean for me? It means I was on investor calls three days after giving birth. Taking calls while my hormones were surging and my body was trying to heal from the most beautiful and body changing, exhausting event I had ever been through.

Add COVID. Leading up to my delivery, I was on the phone with my best friend daily who was also giving birth around the same time. We were scouring the county dashboards to see the infection rates, hopeful we wouldn’t be giving birth in a tent somewhere — or worse, that we would be giving birth alone. No partners.

Will I contract COVID and be separated from my baby for two weeks before I ever have the chance to hold her? Will my husband, in his trips to the grocery store, get it and be unable to be with me? Let’s not forget the realization that we would have zero outside help or in-person celebration as we brought our sweet baby home.

It was scary as hell. The seed capital I had put into the company, my entire savings, was almost gone. I was exhausted. I was dealing with major issues related to staying viable and nimble in the face of the pandemic, despite our offering being in online learning. Things are never as easy as they seem.

The best day of my life. Welcome to the world, Madison Lauren Smith.

I had two days in the hospital with my new baby and husband. All of the expectation and desire culminating in the best two days of my life, free from distraction. Within the hospital, I didn’t have any fear. My baby was there. My husband. And we were beginning our life together. When they placed her on my chest, the only thing I could muster was, “She’s so small.” And she was nearly 8 pounds. Us founders, we always have a way of seeing things differently.

Becoming a mother was incredible, something I had always wanted. I didn’t go overboard planning for her arrival but I did buy the stroller that was ungodly expensive with the bassinet attachment because when I imagined being a new mom, I imagined gently strolling along the Chicago lakefront, where we were living at the time. I imagined slow easy days with my baby and getting to know one another and settling into our new life together: reading books to her, breastfeeding, and bonding.

I now had two days with my baby, my new family. All of my hopes and dreams before I ever even thought about becoming a startup founder cozied up into this little room in the back corner of Broward County Hospital. We loaded our tiny baby into the car and drove the two miles back home, walked in and I knew I had everything I’d always wanted.

72 hours later, I’m on calls. Sobbing to my husband that I just want time with my baby. Living a double life. Being ‘on’ on those calls with general counsel and with the investors as we negotiate final terms. I am in no place to deal with all of this — but I also have no choice.

Being a solo founder can be grueling and devastating.

My hormones were surging. I was experiencing the baby blues as a first time mother, conscious of what was happening but worried that my emotions were out of control. Thankfully my team is incredible and I had done quite a bit of planning to be able to step away in many facets of my job. The world does not stop when you are a founder because you need it to, especially when it comes to negotiating terms of an early stage seed round. There is no one else to do the job.

Being a woman raising money at the early stage, you are vulnerable. There is no way around it. Only 3% of venture capital goes to women-founded companies. We have to fight for every opportunity, have more traction and speak to de-risking the investment, while our male counterparts get asked about how they could really ramp if they followed less predicable strategies.

Through the eyes of traditional fundraising, I was a risk to the investment simply because I was a woman founder bringing life into the world before my company had been given the opportunity to gain real traction. Maybe my grief started during the months I was fundraising, but it reared its ugly head quickly after giving birth when I could no longer ignore it.

I’m here to share my story. To normalize the success of female entrepreneurs. While the world is against us, we are a powerful group. Our challenges make us stronger. The past year, I dealt with Postpartum Depression as I scaled my company. The depression does not need to be tied to a label, though, because we are humans.

I find that writing leads to healing, and sharing is powerful. This is me committing to continue to tell my story so that other women founders and CEOs can know they are not alone. I am here, in your corner, rooting like hell for you.

When people ask about how my maternity leave was, I well up with tears. I am still processing the grief that comes from being a solo woman founder, giving birth during the pandemic and having anger that I chose a career path that made it impossible to step away during the most radical, physically taxing and emotionally surging part of my life.

We’re here acknowledging entrepreneurship isn’t always rosy, especially for women founders. It’s laden with grief. And the process of acknowledging and dealing with that grief — sharing our stories — is what makes us incredible leaders of companies.

Please give me a follow if this speaks to you in any way. Shamelessly, I do need encouragement to keep processing and writing and sharing. This is my first article on Medium, or really any platform. It’s my desire to open up about all things early stage startups — including fundraising, scaling, and co-founder relationships (from my past life) — and sharing my CEO story.

This past year has been a massive struggle through Postpartum Depression and Year 2 of a startup. But I’m here. I’m grieving. I’m celebrating. I’m finding ways to be a healthier person and founder, and I’m grateful for the journey.

Here’s where you can find me as I work to tell my story, on the daily.

Instagram: @myceostory
Twitter: @emilysmithslp

Glutton for early stage startups. Second time tech founder, first time mom. I write about equity in education, tech, fundraising and my growth journey as a CEO.