First comes love, then comes a Series A
I’m generally considered one of the more transparent venture-backed founders growing a company right now. Call it “building in public” or just a loud Twitter persona, but I’ve never known how to relate to people other than by being radically upfront about what I’m thinking.
Yes, this can be a massive flaw. Sometimes it gets me cancelled. Sometimes it sends me viral. For better or worse, it is how I lead.
Still, it was a surprise to many investors, partners, and Catch supporters when I announced I was pregnant — and having a baby with my cofounder — while we were raising our Series A.
I never intended to hide this meaningful part of my life. It was simply that life can be complicated. When Andrew and I started working on Catch, I was married. In the span of 4 years, my marriage unraveled, I got a divorce, I fell in love with my cofounder, and we decided to have a baby. At the same time, we went through YC, raised a Seed round, hired dozens of amazing teammates, and launched huge product features and meaningful partnerships.
One of those journeys I wanted to share with the public, one I did not.
Nevertheless, as I started the process of fundraising for our Series A at 6 months pregnant, I knew I needed to be upfront about a) the baby, b) my cofounder being the baby’s father, and c) what those two things meant for the future of the company.
Today, we’re announcing our Series A, and I want to share what the personal side of the journey has been like.
Your Partner is Your Partner?
I can’t decide whether or not being partnered with your cofounder is common or uncommon. Sometimes it seems like people are shocked, other times women secretly message me saying, “Me too, and we don’t know how we’re supposed to talk about it.”
The truth is, investors don’t want to fund couples. There are bad reasons for this, and there are good reasons for it.
The bad reasons include: what if you get in a fight? Well, there’s some underlying sexism that heavily alludes to women being emotional, but I think the more important take away is: what if other cofounders fight? As a couple, we have a lot more invested in working things out than two random guys who went to a crypto meetup in Venice Beach one time and decided to start a company together.
Don’t get me wrong, I’m sure there are examples of couple founders fighting and crashing the company, but I’m certain there are more than 100x more examples of non-couple founders fighting and crashing the company.
Probably the best cause for concern that I’ve heard articulated is that investors may be worried about the opposite scenario of splitting up from a fight. They’re worried that if one cofounder needs to exit the business or isn’t growing enough to keep up with their role, it will be difficult for a couple to have those conversations because of the personal relationship.
That seems like a fair concern. There are probably cases where this has been a problem. My ultimate response, though, is that if you’re trusting me with making good decisions and managing millions of dollars, you may have to also trust that I can have difficult conversations with my partner.
These and other concerns have made founders — particularly, in my experience, female founders — fearful of the inevitable conversation about being coupled.
“If I don’t tell investors that we’re a couple, it will seem like I’m hiding important information, and that’s not my goal. If I do tell investors, it will seem like I think it’s a *big deal* and might be an investment risk.”
This is a real conversation I had with a female founder, and my only thought was, “SAME, GIRL, SAME.” It’s a tricky balance. Being up front can seem like you believe the relationship poses an existential risk, much in the same way having a pending lawsuit does. NOT being up front can seem like you’re trying to pull a fast one on investors, and you never want to lie to investors.
So the double-bind of a being a female founder is exacerbated. [By the way, I have no idea of how male founders deal with this. Even with my cofounder, it’s never been a particular issue because I am the one who manages our investor relationships.]
In lieu of having to figure out how to tell our investors, we decided to absolutely demolish the hypothesis that we might split up at any time. We decided to have a baby.
There’s so much money right now.
One of the most infuriating narratives is that it is easy to fundraise, that people are throwing money at everyone who asks for it, and that you’d basically have to be some kind of dunce to be unable to raise a round.
I’ve heard it a lot in the last 12 months. Investors have more money than companies to fund. People are looking for places to stuff their money. Monster rounds of hundreds of millions of dollars are announced every single day. Companies that wanted to raise $2M raise $10M by accident.
The reality is not so simple. There are plenty of great companies that aren’t being funded. Some, because they don’t fit the venture model. Some, because the founders are overlooked and underestimated. Some, because contrarianism is even more difficult with so much uncertainty during a global pandemic. Many, because as venture multiples continue to increase, the need to be “right” just once means VCs take on crazier and crazier bets.
Raising money has never been a given in my experience. In fact, the vast majority of people who claim that raising money is easy have never done it or are not doing it in this decade.
Every time we’ve raised capital, it’s been hard. Part of the challenge is crafting the right message: the blend of vision, execution, market, team, and economics can be challenging to explain in a way that VCs want to hear. Particularly for women, the insistence on de-risking means raising big venture rounds is even more difficult.
Still, we have been fortunate and were trusted with a large (in 2019) $8M Seed round. We used those funds to lock in product market fit and build significant infrastructure across banking, investment, and insurance.
In early 2020, our growth started to take off. During our busiest Open Enrollment season at the end of last year, we had more demand than we could handle. It was time to raise the Series A.
Why now?
Casual conversations with investors felt different at the beginning of 2021 than they had previously. The model was working. Capital constraints were holding us back from growing more quickly. Urgency to beat competitors to large partnerships was growing.
Our vision and milestones for the next two years became clear.
But personally, I was languishing. A pandemic that had locked me inside for a year, an ugly election (and the subsequent destruction of democratic norms around peaceful transfers of power), and a developing human sucking the life out of me made it a really tough year. To all of us who made it through 2020 sober, I raise my glass to you.
I knew that trying to raise a round when you are struggling with your mental health is a mission that is doomed to fail. Regardless of how well your business is doing, being unable to communicate and embody the potential and excitement you feel will be obvious to investors. I knew Catch was on to something big, but I knew I wasn’t in the right place to be the vessel for that story.
As I moved along through the second trimester, the urgency of raising the round grew. Andrew and I knew we needed to do something to reset our mental state, to be clear-headed and stable enough to share the story of what makes Catch a multi-billion dollar company.
What if we lived in a TikTok House in Beverly Hills?
We’ve been lucky at every turn in building this business. One of the most serendipitous moments came during the winter of languish. A random Twitter DM from @callmehouck offered up a chance to go to LA for a month.
After a quick FaceTime tour of the mansion and a conversation with Houck about what we were working on, we were offered a spot in the 4th cohort of Launch House. Andrew and I knew that we’d be among the oldest people in the house, but we were desperate to push our own boundaries and create new connections.
We flew to LA for a month to live with a bunch of strangers. It was like The Real World, except I was pregnant and had to raise our Series A.
I’m Catch’s biggest fan
We were absolutely right that living in Launch House would change everything. These founders and influencers had unbounded optimism, vision, and hunger. It was YC, but with sexier branding and summer camp vibes. We cooked, cleaned, and took out the trash while discussing NFTs, Web3.0, and whether or not you should run a country like a tech company. (My answer for the record is a resounding NO.)
I started pitching investors. I was reminded that I am the biggest fan of what our company is and the torchbearer for what we can be. Our accomplishments were put in perspective as young, new founders looked up to us for advice on everything from picking a name to handling a cease and desist.
Doing all of our fundraising pitches on Zoom meant that I got to choose when and how the information about my pregnancy was shared. Although I HATE doing second and third follow ups on video call, I felt lucky that I could own our personal story and not be given away by a quickly growing tummy.
I was finally confident that announcing the pregnancy was no longer a risk: it was a screening mechanism that would keep away the type of investors I had no interest in working with. In some cases, a pass felt like dodging a bullet. Each subsequent yes gave us confidence we would get to choose to work with the investors who would be most likely to help us succeed.
We found our lobster
For those of you who don’t know the reference (shame!), an episode of Friends describes finding your other half as finding your lobster because lobsters pair up for life. Choosing a lead investor for your Series A and Board is a decision that can reverberate through your business for a decade or more. We wanted to be sure we would be working with the right people.
From the first conversation, David Silverman and Gabby Contro at Crosslink Capital were people I wanted to learn from and work with. They were warm, curious, and ambitious. I felt an immediate connection, and after more calls, due diligence, and even a few difficult conversations, Gabby flew out to meet us in person for dinner and a term sheet. We knew they were the ones.
The baby and the business
We closed the round two weeks before I gave birth. Our new addition, Austen Leigh, is the light of our lives. As we adjusted to parenthood and relocating the company to New York City, we have had the opportunity to reinforce where we’re headed.
Becoming a parent has a funny way of helping you prioritize. It shows you where you were more involved than you should have been. It keeps you from wasting time on things that don’t matter. I’ve always considered myself a ruthless prioritizer, and now my abilities have been sharpened.
Our revenue growth has accelerated in the weeks following Austen’s birth. Our team is expanding. Our product is being refined and improved. The next two years of milestones that Andrew and I are looking forward to now include first words and first steps, but we’re more certain than ever that we’re in the early days of building a huge, iconic company and a tiny, miraculous human.
Read more about what we are doing with our new funding.
