Lessons learned from raising capital while pregnant

melissa fensterstock
4 min readMar 8, 2022


Photo credit: Melissa Fensterstock

There was a period of time when I faced rejection on a daily basis, literally everyday. Not from lovers but from investors. I would wake up to an email politely (or impolitely) saying “Pass” “Not for us” “It’s not you it’s the business” “Keep us posted!” It takes a tough stomach, perseverance, and belief in yourself to prevail.

I raised about $5M of mostly angel money. Blood, sweat, and tears money. Checks ranging from $25K to $1M. Each check involving networking, prep calls, calls, post calls, diligence, background checks, legal docs, and beyond. Oh and BTW I was pregnant.

Is raising capital for women is harder than for men?

The statistics say yes, but I am not a statistic. I never thought of myself of being at a “disadvantage.” I was me. I was Melissa raising capital. I was the same as anyone else making investor rounds. Sometimes I think we let our fears get in our way and we let stereotypes cripple us. In my first-time efforts, I didn’t have anything to compare it to. Naivete is a beautiful thing. Was it harder than it was for men or was it just goddamn hard?

The black poncho is your new best friend

About a week after I signed my legal docs with Landsdowne Labs I found out I was pregnant. Really, could the timing have been any worse? Expletives raced through my head. I just started working with a new set of cofounders, pitching to strangers, and signed up for a super intense job, and now I’m having a baby? How might that go over? I didn’t think investors and strangers who didn’t know me could factor in this additional risk beyond the risk of a startup. They would certainly say no. This was super tricky to manage, and in retrospect I am very happy with the outcome.

It was May. Baby due in December. This meant I had until October to get my funds committed before the pregnancy became too obvious. This was pre-covid and meetings were still mostly in person (Pandemia and Zoom have been a blessing for pregnant female founders). So, I hustled really hard and secured a term sheet in September, all according to plan. Now, I had to round out the round. The black poncho became my bestie. What better attire than a loose-fitting poncho to wear out and about? People who had never before met me wouldn’t see a belly and would never dare to ask. For people who had met me before, they might just assume I put on some weight? My last in person pitch was the 2nd week of December. My second son arrived on Dec 23rd. No one in that room batted an eye or asked any questions (score!).

Be your amazing, authentic, passionate self

I get that having children is life changing. Will mom want to work afterwards? How might priorities and perspectives change? I was committed to my business, and I knew it 100%. It was no one else’s business. They would see for themselves. I worked right up until labor and picked up just after. No maternity leave. With a team of 1 (1 being me!) there was no room for a break or maternity leave unfortunately. Do I wish I had that luxury? Absolutely, but that wasn’t the case here. I closed my round on Jan 22nd just 1 month after giving birth. I was able to find the energy and the motivation to get out of bed each day because I truly loved my job, my life, and my purpose.

While most women would have been on maternity leave, I tried to time calls around baby’s naptime. Sometimes, plans failed and I had a screaming newborn in the background. Laptop in one hand, baby in the other, phone on my shoulder. I prefaced calls by saying please excuse any background noise as I have a newborn. Most people got it and were understanding and sympathetic. I remember bringing my <4-week-old son to in person meetings. Most memorable was when I looking for lab space. Meeting a male real-estate mogul, I nursed while talking and subsequently completed a total wardrobe change (on a desk) due to an overloaded, foul diaper (Shout out Carter Winstanley thank you for being so cool about it).

All in all, I wish I could have shared my pregnancy. It’s a sad truth that I was afraid that statics and stereotypes would hold true. I was not willing to put my venture at risk to test it.

It’s all about the people

Investors know it’s about the people. Ideas matter but at the end of the day it’s the CEO that holds everything together, especially in the dark days. There are so many unknown unknowns and the founder has to be resilient enough to persevere. If you love what you do, it will show and shine. Of course the product needs to be top notch, you must know your stuff, and the terms of the deal need to be appealing, but it’s the founder that ultimately inspires, leads, and with conviction brings others along in support. Enthusiasm and positive energy are contagious.



melissa fensterstock

Deep Tech VC, Life Science Entrepreneur, CEO, Anti Procrastinator, GM of Household, HBS grad