Every six months, the full Jawnt team comes together from Philly, Boston, LA, SF, Portland, St. Louis, and beyond for our semiannual offsite: the Jawnt Jaunt. It’s the best time of the year on the Jawnt calendar—a chance to revisit our mission and vision, dive deep into our product, and come together to build the future of transportation technology.
This time, we gathered in New York City, a public transportation paradise that shaped our founders’ earliest ideas about access, mobility, and transit. We walked past Jeff’s old apartment, heard stories about Will’s four years across four boroughs, and tried to soak up as much transit magic as possible in 72 hours.
Between whiteboarding sessions, strategy breakouts, and way too many fried Oreos, we came away feeling even more fired up about what we’re building—and where we’re going next.
In the rest of this blog post, we’ve given you an inside peek into what makes the Jawnt Jaunt so special—and why we’re pumped about building the future of transit passes.
Day 1
The team traveled from near and far—by subway, Amtrak, and plane—to arrive at our hotel in the Flatiron. Some folks were shocked by the architectural brilliance of the “New York-sized room,” but other than that, things were off to a great start. The JJ kicked off with dinner in the East Village and an obligatory stop at Ray’s Candy Store, near Jeff’s old stomping grounds.
Day 2
The weather was perfect—50s and sunny—and we started the day with giant New York bagels topped with lox and whitefish. The agenda: reviewing our mission and vision, digging into company culture, and breaking into small groups to workshop key upcoming projects.
There’s a lot to love about being remote-first, but there’s nothing like getting in a room together with a whiteboard. Picture this: Austin from Finance, Kaleb from Engineering, and COO Will architecting the future of Jawnt in one room, while Ruth from Partnerships, Leo from Community Engagement, Edwin from Customer Support, and I jam in another. It’s a pretty special vibe. I wish we could share more, but for now… stay tuned.
Day 3
Day 3 was all about transit and understanding how New Yorkers really get around. A few folks started the morning at the Crain’s New York Power Breakfast, where the Chair & CEO of the MTA announced that they’re officially phasing out the MetroCard. Definitely a bittersweet moment, but felt like fateful timing as we look to bring the modern Jawnt Pass to NYC.
The rest of the team split into two groups to bop around the city: one on Citi Bikes, and the other by foot. The biking crew cruised the perimeter of Manhattan, stopping to dock and take in the views. We made sure Citi Bike is a benefit on the Jawnt Pass—we’re excited for New Yorkers to get around just like we did. The walking group clocked over 10 miles (my personal count!) and made some iconic stops, from The Strand’s NYC urban planning book collection to a sunny stroll across the Brooklyn Bridge. During our walk, we hopped on the subway at Washington Square (shoutout to the amazing performers we stopped to see) to make it to lunch—another reminder of how essential and convenient transit is in New York.
We all met up at Time Out Market in DUMBO and brought our lunch to Brooklyn Bridge Park, where we soaked in the Manhattan skyline and watched influencers doing photoshoots (it’s just not the same in Philly).
Next, we headed to the Transit Museum of New York City for a private tour. Cannot recommend this place enough—we got to sit in subway cars from the early 1900s and learn about the fascinating history of NYC transit. It’s worth going to get the full scoop, but I’ll share some fun facts we leaned:
- The first subway line opened October 27, 1904, from City Hall to 145th Street (just 9.1 miles, 28 stations).
- Despite being a brand-new concept, over 150,000 people rode the subway on day one.
- The fare was just $0.05 until 1948!
- Two companies used to run NYC subways—the IRT and the BMT—until they were unified in 1940. If you’ve ever noticed that lettered trains are wider than numbered trains, this is why.
- Ridership peaked in 1946 with over 2 billion rides in a single year (5.5 million per day!). In 2024, the subway system has more lines, but ridership is at 1.95 billion.
If you do go, it’s worth noting the museum is in a decommissioned 1936 subway station in Downtown Brooklyn. At first we were confused—we had to walk down stairs like we were catching a train–and then we realized this made the museum especially interesting.
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After the museum, we explored the city in small groups. We brought disposable cameras and captured shots of a day in the life. Keep an eye out for lots of photos of dogs in Prospect Park and pickup basketball on the piers dropping on our Instagram page.
Our final dinner was a big Chinese meal with a massive lazy Susan. We swapped stories about getting around the city and left feeling even more excited about what we’re building.
Day 4
By Day 4, many of our email inboxes needed some love. We spent the day working together at a coworking space, easing back into the swing of things—customer meetings (new logos dropping soon 👀), ordering transit passes for our existing customers, and starting to build the new features we’d brainstormed earlier in the week. Like any good team event, I was feeling both exhausted and energized, ready for a good night’s sleep at home before getting back to building the future of transit pass technology.
What’s Next
I’m already thinking about our Fall 2025 Jawnt Jaunt, but until then, we have a lot of work to do. We’re focused on growing the team, giving our customers the best possible experience, and getting as many people riding as possible. We’re jazzed about the future – thanks for being along the ride with us!
