Summary List Placement
It was the last week of February 2020, and my cofounder and I raced down to the subway platform after a promising meeting with an investor and scooted onto a wooden bench.
I grabbed my laptop, threw it open, and furiously started updating a forecasting model to answer follow-up questions about the company I was about to build. The energy in that station was palpable. It radiated from my excited cofounder, the express trains whizzing by, and the groups of tourists with Eataly bags whose thrill about their ball of burrata had nothing on the intoxicating knowledge that I was on the verge of something big — and that investors recognized it, too.
Then, a week later, as if some omniscient being had pulled the emergency brake, the world stopped. Handshakes that had been replaced by elbow taps were suddenly replaced by greetings of, “I think your mute button’s on.”
We were first-time founders who were starting to see the seas parting, but suddenly those sea levels were rising, making the path to funding seem impassable. We already had a disadvantage as female founders. To add a worldwide pandemic to the list of barriers would seem almost comical if not for, you know, the pandemic.
When COVID-19 hit New York City, we had barely gotten our company off the ground, having just signed our incorporation papers, and it felt inevitable that the pandemic-panicked market would force us down closer to the pavement.
But then — it didn’t.
In mid-March, almost in an instant, the collective behavior of humans worldwide shifted to place less priority on optics and more on substance, whether in our personal lives (why get that haircut when you can spend that money for COVID-19 relief?) or in the workplace (maybe that skyscraper office in the Financial District wasn’t quite worth the layoffs).
What mattered in February suddenly didn’t in March, and that extended to everything we had been told about fundraising up to that point, too: Make sure you dress cool. Make sure you act cool. Just be cool, and the money will fall into place.
Except “cool” doesn’t cut it in a world where everyone is thrust into uncertainty and the confines of a 13-inch screen.
Power suits had to be replaced by powerful pitches that showcased the strength of your idea and depth of your experience and knowledge. Emotional detachment had to be replaced by empathy for the person on the other side of the Zoom screen who’s balancing young kids with potential economic calamity. Flashy boardroom presentations had to be replaced by poorly lit meetings where storytelling trumped glitzy graphics.
The entire fundraising process had changed — as my still-unredeemed voucher for a canceled March 24 trip to San Francisco can attest — but, as it turns out, all this suited us quite well.
Despite already having grown a company from zero to an audience of 80 million monthly readers, my partner and I would still be considered unlikely founders. Without a technical background and deep pockets of our own, launching a company was a risk, particularly for two people who look different than 97.2% of entrepreneurs who receive investments.
But what our pitch lacked in coding skills and maleness, we made up for in substance. It wasn’t just about the showmanship of the pitch — we had spent the months leading up to our meetings developing forecasting materials and operational blueprints, based both on thorough research and our more than 20 collective years in the industry.
We had the Big Idea, yes, but we also had experience building and operating a business. We had the story, yes, but we also had a sophisticated plan that showed we could execute it. We had industry foresight, yes, but we also had flexibility to be able to roll with the punches, as evidenced by [gestures broadly].
And, not to mention, we also had heart. Replacing surface-level chitchat about the slopes in Vail with vulnerable conversation about our day-to-day struggles — with childcare, fear for our parents and grandparents, fear for humanity, and so much more — allowed us to forge deep connections with several investors that continue to this day. (If you’re not still checking up on one another, by the way, you should be.)
Pre-COVID-19, we thought fundraising to launch The Dipp would take months. Post-COVID-19, we thought fundraising might be a dead end. But just three weeks after that tourist waited in line at Eataly and stepped down to the 23rd Street subway platform where two women were tapping away on a MacBook, we received our first term sheet and closed $2.5 million shortly thereafter.
I don’t think any founder would necessarily look back at their fundraising experiences fondly. But in writing this — I finished exactly one year to the day after seeing that term sheet hit my inbox — I’m thankful for the relationships I built and for how the industry changed.
And when we slowly but surely begin using our MetroCards and miles again, I hope we continue to value substance over style. That we continue to value one another and show empathy. And that, in 2021, female founders make up for more than just 2% of investments. Now, that would be cool.