In early 2015, shortly after launching Chaac Ventures, I made my first big fundraising trip to New York.
The trip was mainly to visit with an investor, whom I had been told was a big hitter. I knew that closing him would lead to big things for our young company, so I was laser focused and had prepared like crazy.
That morning, I shaved, put on my best suit, had my shoes shined, and rehearsed my answers walking to the office.
What is Chaac’s investment thesis? Check. Our diligence process? Check. Who’s on the team? Check. Check. Double Check.
The sun was shining. Not a cloud in the sky.
I took a deep breath, entered the Manhattan office building, rode up to the 40th floor and was escorted to a large conference room with floor-to-ceiling windows.
Shortly thereafter, four members of the investment team — all at least 25 years older — entered the room wearing golf shirts, khakis and the ubiquitous fleece vests.
Each one had a notebook and a printout of our investment overview. We shook hands, exchanged pleasantries, and I awaited the first question:
“So, what the hell does Chaac mean?”
I blinked for a second, then jumped in:
“Chaac is the Ancient Mayan god of rainfall and fertility.” I said.
“He strikes the clouds with lightning, bringing the rain and the thunder, and that is what we do as seed investors. We bring the rain, thunder, and nutrients to help support our early stage portfolio companies.”
“And, how do you do that, exactly?”
“We do this by trying to make great introductions, helping with strategic ideas and initiatives, and supporting our companies however we can. Hopefully, we can help them grow into prolific, once-in-a-lifetime companies, making the world a better place, and also making it rain for our investors along the way.”
Then, the next question. One that I would go on to be asked hundreds of times thereafter.
“And… How old are you?”
“You do realize that most venture capitalists are at least in their 40s or 50s, right? What makes you think you have the experience?”
And there it was. The proverbial rain on my parade.
Outside, the skies became dark, and it began to pour. I gave a shortened version of my usual answer, and just like that, the meeting was over. It had lasted approximately 14 minutes.
Even though I thought my answers to their questions were fine, I still had a feeling in my stomach like I had failed. I was demoralized, and now, soaking wet, walking to the subway.
My clothes dried a little bit on the E train out to the airport. My phone buzzed with a message notification when I came up at Jamaica Station. Some good news, finally, I thought.
It was a text from Wells Fargo: You have been charged with an overdraft fee on your checking account. More rain.
I boarded my Virgin America flight and sat in the last row, middle seat.
“Ladies and gentlemen, please be advised that we are being held on the ground as a band of thunder and lightning crosses through the Midwest region. We’ve got some weather!”
This was a painful day for me as a founder. Now, I see it for what it was — nourishment from the VC gods.
While rain can nurture and speed growth (what we try to do at Chaac), at the same time, rainy, gut wrenching days can be brutally cold and sting like needles.
Some founders and people have the ability to tough it out in the nastiest of conditions and grow stronger from those cold needles of rain.
Having grown up around these types of people has certainly helped me stay on the path and pushing forward, despite how hard the path may get.
I remember another a stormy day about six years ago. It was my senior year at Princeton. Our lacrosse team met at 5:45am for a pre-season run test.
Not only was it pouring, but it was freezing cold as well. Chris White, my roommate, was our team captain, and a close friend.
Chris is from the western part of Pennsylvania, near Pittsburgh, so he had experienced his share of dark, rainy days.
We sat in the dark, chilly locker room and listened to the rain beat down on the roof. Not a happy group.
Half of the team was grumbling and crying about the rain, and Chris had heard enough. Moving to the front of the room, he told everyone to listen up.
“Look, guys. I know a lot of you are unhappy about the rain, and it sucks that we have a run test this morning, but let me tell you something: we are lucky to be able to do this.
We are lucky to be on this team, to have each other as teammates, and to be able to go out
there and run around and have fun. So it might be pouring, and today’s weather may suck, but shut up and embrace it.”
He then went to the white board and scrawled those famous words, EMBRACE THE SUCK.
The spirits in the room lifted and the energy level picked up. Chris’ words helped us power through not only that run test, but the many challenges we faced all season.
The rain had ceased to become a foe. It started to inspire people and had become just another obstacle to overcome. We grew stronger individually as well as a team because of it.
I now live in Southern California, where the rainy season is tricky. On the one hand, you sort of don’t mind the rain, because sooner rather than later, the sun will be back, and all will be beautiful and comfortable again.
On the other hand, the rain is so powerful that it can cause massive damage, quickly.
Calm, beautiful places like Malibu’s Pacific Coast Highway, can turn into horror shows quickly, with flash floods and mudslides, which feels like a metaphor for startups.
In the long term, the rain acts as a natural market force, weeding out weak players — houses built too precariously on bluffs without proper foundations — and making the system stronger, as people will rebuild better, stronger houses on the sites where an old house is now sitting smashed on the PCH.
For others who are able to endure the rain, they can go on to become sustainable companies and institutions for years to come, rain or shine.
A few months after the rainstorm meeting in New York, I was sitting in traffic in LA and it happened to be pouring.
I had received emergency texts and flash flood warnings when the phone rang.
The call was from an investor we had pitched weeks earlier — not the one in New York — this time, an investor in Florida.
She told me she loved what we’re doing at Chaac and wanted to set up a follow-up meeting to discuss making an investment in our fund.
I will never forget the sheer level of excitement and happiness I felt, as I sat in my car with rain and falling from above.
When we were brainstorming names for Chaac (we started with Greek gods, but that was so 90s), we stumbled across a site about Mayan gods, and found it to be a cool metaphor; the rain god, Chaac, resonated with us.
But when sitting in a sunny café in Santa Monica, one tends to think of images of a light spring rain, huge drops welling up on lush green leaves, about to roll off into the verdant grass below.
The rain stops, a rainbow emerges, and tiny sprouts shoot into strong, vibrant plants. That’s what we envision about our future as a seed stage VC.
The reality, with weather and startups, is far different. The rainstorms can be brutal, the damage swift and massive, leaving one to pray for a safe port to come in out of the storm.
But one way or another, the sun eventually does come up, and those left standing are stronger for having survived.
With our own company, we are lucky to have had mostly light rains that were followed by beautiful rainbows. We also have days that feel like torrential downpours.
In any event, I certainly have a new appreciation for the power of the rain. Survive the downpour, and sunnier days right around the corner.