Retreat to Move Forward: Our 36 hour getaway in the name of company culture, values and purpose

Katie and I spend a lot of time together. A lot of time together. We sit in the same 4-person office every day. We live at most one block apart. And we share so many friends from grad school that even away from the office we end up seeing each other. Just this morning I stepped out of my building to head to the gym and immediately saw Katie across the street taking her dog George out for his morning walk. There’s no real escape. 

So, oddly enough, Katie and I left New York City this weekend for a one night trip to the Catskills to spend even more time together, as though we needed more of that. Spoiler alert: turns out, we did. 

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We took this weekend to get out of our usual routine, get some fresh air and get some room to think. As early stage founders (read: very early), we’re inclined to want to run at a million miles an hour. We’re inclined to move quickly, build things and break things and spend more time doing than thinking. There’s this pressure to do now, think later and hope that you learn from the mistakes. 

One area that requires a lot of thinking though is culture. And values. And making sure that we’re inspired and motivated by what we do every day and that we’re giving this the absolute most that we can. It’s important to the both of us to be able to articulate what gets our minds inspired and our hearts in it. We want to be able to hone in on the words and language of what it is that we stand for and what that means both internally and externally. It requires a combination of planning, honesty and self-awareness to be able to say this is what I want to build and here’s why. 

Getting out of the city felt like the best way to get closer to those answers and the best way to get closer to each other. The car ride up on Sunday got us started where we talked about our childhoods and upbringings and stories buried within each of our respective families. The question of “Do you ever wonder what your mom was really like when she was your age?” made me cry and made Katie speak with complete candor. 

By the time we got up the mountain, Katie luckily agreed to a condensed and less strenuous hike given our timing in getting there that afternoon. But even watching Katie on that hike exposed me to so much more about her. There’s something about the way she hikes that is so unequivocally her. She skips, she climbs, she jumps on and off of anything she can find. She has a child-like sense of curiosity and exploration when she’s outside, looking for snakes and frogs and truly any animal she can get her hands on. It’s the spirit and excitement that makes coming into work every day so fun. It’s the same spirit that makes her one of the most driven and motivated people I know. Taking her out of the Soho jungle and into the woods unlocked this other part of her. 

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Later than night, we got back to our hotel and had an epically long dinner where we ordered approximately 5 full plates of food between the two of us and did the NYT 36 Questions to Fall in Love. It was truthfully the first time I did that exercise in its entirety (minus the prolonged eye contact because neither of us needed to feel that uncomfortable). The next morning, we sat at breakfast and brought it all together. 

We tried to piece together the snippets of the weekend - from the stories of who we are to the moments that make us feel the most alive to the values and principles we carry with us wherever we go. Our company culture is still not in its final draft stage. Neither is our mission. If this were 1998, we certainly wouldn’t be ready to laminate it and lock it in. But we have on paper the language we love and the words that feel like us. We have the spirit of what it is that we’re building. The pieces are all there now for the first time. Now it’s just about trimming. 

Going into the weekend, I was skeptical about why we needed a getaway for this. It felt like something we could do out of New York without having to drive a few hours, but the truth is that without dedicated time, it’s easy for these culture and value conversations to get lost in the chaos. Everything else can feel more important or more urgent. It feels like the piece that will solve itself without intention. This weekend changed my mind - I feel closer to Katie than I’ve ever been (I’m just as shocked as you are because I really didn’t think it was possible) and I feel closer to what we’re building. It feels like a reflection of us. It feels tied to something bigger than a company and selling product. It’s cheesy, but it feels like something that stirs our souls.

We’ll probably do this escape again as we scale and as we continue to grow and evolve. I’m just hoping Katie lets me pick our activities on the next retreat. Maybe near a mountain, but not on a mountain.