How I landed a $40 million investment just days before I delivered twins

I’ve always been drawn to scale.

My favorite career moments have been ones like witnessing the rapid growth of Obama’s presidential campaign as I worked on it in 2008 or watching the startups I’ve worked for find inflection points that catalyze dramatic growth in users.

I’ve spent the past five years in pursuit of scale on behalf of Guild Education, a company I founded to help the 64 million Americans without a degree go back to school debt-free. On the heels of Guild’s recent Series D financing round and as my twin girls’ second birthday approaches, I’ve been reflecting on Guild’s scale moments and what it’s taken for me to scale alongside the business.

Guild operates on an academic calendar, and 2017/2018 was certainly our inflection point for scale but also one for me personally. I’m not a regular subscriber to fate, but after I had a dream about having twins, I wasn’t surprised when my OB shared that I was expecting not one but two babies. With no family history or science to explain it, it felt like the universe reminding me that I’m built for scale.

I was equal parts delighted and terrified about the impending birth of twins. I was already short on role models of how to lead as a female CEO, let alone a pregnant one. And there was certainly no rulebook for a CEO maternity leave. So I charted my own plan and wrote a letter to the company.

I wanted to be as transparent as possible, so I tried to lay out the known and unknown realities ahead. I didn’t know how I and the babies would recover from labor, or whether we’d spend time in the NICU, as is common for twins. I told them that I didn’t know how long it would take for my body to figure out how to breastfeed, how many all-nighters my husband and I would actually be pulling, and most importantly, how my head and heart would feel when torn between my first baby, Guild, and the two new human babies I was bringing into the world.

I told the team that whatever I chose would be rooted in flexibility and optionality. Rather than use my own experience to create the Guild blueprint, I emphasized that I would lead by offering choices and space for each employee at Guild to do what is best for them when they have children of their own.

Fortunately, we had just wrapped up our Series B financing, so I was at least able to cut fundraising off the to-do list, eliminating another obstacle that seemed critical. I had heard horror stories about the conscious and unconscious biases that come with fundraising while pregnant, and I wanted to avoid it at all costs.

Flash forward to the last week of March 2018. Guild was growing even faster than expected, and I was seven months pregnant with no expectation of making it to full term. That’s when I got a note from Wes Chan at Felicis Ventures, an investor we had been in conversations with during our Series B in 2017. He was headed to Denver and wanted to wish me well before the twins came. Given my current state, I made clear that we weren’t ready to begin discussions around our next round of funding, and I was barely mobile, but would happily host him at our office (with my feet up).

Wes showed up at my office with a baby basket with essentials like blankets as well as wildly thoughtful additions, like a programmable doorbell that could prevent a delivery from waking up napping babies. Beyond the thoughtful gifts, our conversation reminded me why we liked him and his team so much in the first place. Wes, a first-generation college student himself, understood our desire to align mission with margin, deeply believed in our work, and could connect with both me and our students on a personal level. At the end of the meeting, Wes handed me one more gift: a term sheet to invest in Guild.

I was a bit speechless, and then I immediately started spewing out all the reasons why this couldn’t work. I was about to give birth any day, I didn’t know how long I would be out of the office, and most importantly, as a company, we hadn’t planned for a financing at this time. Despite my hesitations, I huddled with my team and conferred with our board, and we came to the conclusion that this was a great opportunity for the company to continue scaling to serve more students. We determined we could make it work to raise our Series C at that point, but it had to be on our timeline. I called Wes back with a nearly impossible condition. We’d raise the round with them, on the commitment that we’d finalize the term sheet and all key negotiations before the babies arrived, which at that point was anywhere from that minute to five weeks away.

Thankfully, team Felicis was up for the challenge and managed to pull together the full $40M round days before I went into labor on May 2, 2018, welcoming Magnolia and Lily Grace into the world. More impressively, team Felicis ran the whole process in a way that was incredibly supportive and respectful of the space I needed to take care of myself leading up to labor, and immediately thereafter as the final components of the deal came together. I owe tremendous thanks to my team, specifically Mae Podesta, my board, and the Felicis team for letting me enjoy those first few months with my girls while taking care of business back in the office.

While my experience fundraising while pregnant was by no means the norm, there’s no reason it can’t be. If we want to encourage entrepreneurship beyond the age of 24, we need a system that creates the opportunity for mothers and fathers alike to navigate the key milestones of startup life alongside those of parenthood.

We need more CEOs–both female and male–to commit to giving their employees space and choice to pursue ambitious career goals as well as ambitious family goals. And we need more leaders to use their own maternity and paternity leave to set a positive example for their employees. I’m committed to making this a reality at Guild, and excited to support other CEOs and leadership teams to do the same.

Rachel Carlson is the CEO and Cofounder of Guild Education.