How I raised a $1 million seed round when I was 9 months pregnant

Photo credit: Brian Wolfe

The last time I needed a doctor’s note was in elementary school. That was, until last September — I needed a note from my OBGYN proving I was only 31-and-a-half weeks pregnant so I could board a plane to San Francisco with fair odds I wouldn’t give birth to a mile-high baby.

The first thing my doctor asked when I made the request was if I would prefer he write a note to my boss saying I shouldn’t fly at this stage of my pregnancy.

The first thing my doctor asked when I made the request was if I would prefer he write a note to my boss saying I shouldn’t fly at this stage of my pregnancy. As the CEO of my company, I kindly explained that I didn’t think it would help the situation.

I was in the middle of raising a $1 million seed round for my startup, Honey. We are reinventing the corporate intranet with a product that is fast, inexpensive and fun to use. I was excited about an investor in San Francisco; after a series of great Skype meetings, he invited me out to meet the rest of his team as the final step of the process.

At seven months pregnant, even a subway ride was challenging — the prospect of a six-hour flight was daunting. But how could I let that stand in my way? I booked a last-minute ticket and prayed I’d be able to swap my assigned middle seat with some compassionate person.

I didn’t get the funding in California. I’ll never know why, and I didn’t have time to worry about it: The final days of my pregnancy (and my company’s runway) were quickly approaching.

The first day my morning sickness set in, I presented to 800 people at NY Tech Meetup. I won the startup pitch competition at Internet Week while wearing maternity jeans. And I landed first place at July’s UltraLight startup competition despite my baby kicking me in the ribs throughout my presentation. The true fundraising didn’t start, though, until just around the time I started showing.

For months I struggled with the question of whether I should bring it up in meetings. How would investors react? How do you casually slip something so personal into something so professional? Would I sabotage opportunities if I didn’t tell investors and they found out later?

Could I really get away with wearing Supergas and maternity jeans to every meeting?

In this image-obsessed world, would investors critique me less harshly if they knew I was pregnant and not just 40 pounds overweight? Yeah, 40. Could I really get away with wearing Supergas and maternity jeans to every meeting? What would I do when investors wanted to meet for a drink? Was it my responsibility to help pave the way for other women who will face similar challenges?

At a certain point, my body made the decision for me. Reactions were all over the place. Some investors just wanted to talk about their children and grandchildren, others gave me a hard time about drinking coffee, working too hard or being out in the cold. A few told me I should really take the time to stay at home with my child and worry about work later. Others just got awkwardly quiet and stared at their notebooks for the remainder of the meeting.

Three weeks before my due date, I got an email from Nicolas Wittenborn of Point Nine Capital. He was in New York City for a few days and wanted to meet. I booked an hour with him the following morning, nervous that if we scheduled it for any later that week I may need to cancel from the delivery room.

He walked in unfazed. We spoke about how wonderful building a family is and how great it is to have love for two babies — my company and my soon-to-be-daughter. The rest of the meeting was spent in product and cohort analysis. He was able to embrace the fact that I was about to become a mom and also see that my team and I were building something incredibly special. He never doubted both could happen at the same time. When he walked out, I knew we had found the perfect partner. We had a term sheet from Point Nine in less than two weeks.