We took our first company retreat 1,400 miles across the country, on a train.
August 24, 2023
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I’ve always wanted to have a meeting on a train. I love the train (because I love old-fashioned things) and in my mind, a company retreat in the observation car of a train moving across a beautiful landscape felt like an amazing way to find focus for the school year ahead. So, once the craziness of our back to school season was done and every pack was delivered, Alpaca set off on our very first company retreat. On Amtrak. For 38 hours. For 1,400 miles from Omaha, Nebraska to Truckee, California.
I wasn’t sure if the team was going to go for this, and honestly, they weren’t sure what to expect. But the thing about a train is that once you’re on it, you can either learn to love it or get off the train. So no matter what, it would be an experience. This team is amazing and game for anything, so I knew we’d have an adventure.
It was an incredible ride through parts of the country you can only see by rail, and best of all, it took us away from Alpaca’s office and operations (and packs, and mini erasers, and tubs of hot glue guns), and into a couple of days to focus on what we wanted to achieve as a company and how we were going to do it.
Here are the five things we learned, and the big reasons I would do it again in a heartbeat:
We found deeper conversation in an analog retreat.
If you’ve ridden Amtrak lately, you know: the internet is a hit or miss situation. Through entire parts of Colorado, it simply doesn’t exist. For our team, this meant that we got out our pens and post-its and focused on real discussion about the future of our company. Each morning, we gathered at a table in the observation car, rolled out our paper, and then asked big questions, made lists, sorted ideas, taped things to windows, and prioritized efforts for the months ahead. The act of writing things down held value, and the process of bringing them back to our digital life when we returned made us ask once more “what did we decide here?”
We found focus in an ever-changing environment.
What the train lacks in internet, it makes up for in scenery. In a lot of company retreats, you’re sitting in the same room in a hotel or conference center for two days, often without a lot of windows. For the Alpaca team, we regularly paused a conversation to marvel at the surroundings – mountains, wildlife, sunrises, sunsets. We even jumped off the train at one stop to not miss the farm peaches for sale along the tracks. But even with the distractions, we kept the conversations going all day and into the evenings, focusing hard on the biggest challenges in the company.
Reflecting back, it felt like an important analogy for building a new company: how do we continue to find focus in ever-changing market environments, with an always abundant list of ideas, and countless opportunities to consider?
We got uncomfortable. And we liked it.
Amtrak is a little like camping while moving. It’s not luxurious. In our 38-hour journey, we ate five meals in the same dining car, with the same menu. Everything is small, and the quarters are close. It’s easy to get a little motion sick. Our intrepid little crew found a lot of productivity, and honestly some joy, in those hard parts. We used a long delay (because, honestly, we hit a cow… not joking) to get one more marketing conversation in, and then recapped the stories once we were in the fresh air in Tahoe. It was a good reminder: that we are small, and scrappy, and we know how to do hard things like hauling hundreds of boxes around in a U-Haul to save some money on shipping; or staffing the booth for 12-hour events just to get our name out there. Uncomfortable is the name of the game for a lot of early stage companies, and this was a good reminder that we can not only handle it, find joy in it, and be proud of the outcomes.
We met a lot of our future customers, from a lot of different walks of life.
Like a lot of teams in early companies, we can get a little myopic about who our customer is today and project that into the future. But it turns out, parents and grandparents who want better ways to support their teachers look really different, have different challenges, see different things in their schools. And guess what? All those different kinds of people ride the train. We met parents from all parts of the country and all walks of life. It was a truly humbling reminder that we have a lot to learn as we take Alpaca to new cities, and that our job is to keep learning about our future customers.
Curious strangers helped us with our elevator pitch.
I’m going to tell you what most people on the train do not understand, and that is WHY anyone would have a company retreat on an Amtrak train. We got a lot of raised eyebrows about our post-it notes. We got a lot of questions about what we were doing. We got a lot of questions about who we are and what we’re setting out to do with Alpaca. Sometimes there was a lot of time to talk about it and sometimes there was just a moment, so we had to get good at both.
When we got off the train in Lake Tahoe, we reveled in the fresh air and non-train food. But we also reflected back on our 1,400 mile experience that built awesome foundations. We came away from our daily trips to the observation car knowing we’d built out excellent strategies and stronger relationships. We had clear plans for marketing, operations, and customer success when we got back to the office, and we had a better sense of each other’s strengths to achieve those plans.
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