November 2025
Dear Driver,
As we turn the corner into November, I find myself reflecting on how far we’ve come with The Driver’s Seat. We may not yet be cruising at full speed, but building something meaningful takes time, and I’m proud of the progress we’re making together.
Speaking of progress, OCToWEEN 2025 was one for the books! It was our most active celebration in recent memory, and the creativity you brought to the CARstume and Dead Ringer contests was outstanding. I’m still laughing (and maybe slightly blushing) over how many of you dressed up as… well, me. Flattering? Maybe. Humbling? Definitely. Either way, it made my month.
I’ll admit, as the year winds down, I’ve hit a bit of a creative speed bump. But that’s not despair talking, it’s just the rhythm of a busy season. There’s still plenty of fuel in the tank, and we have some great community moments ahead. Next week’s food centric FALL-Nighter 2025 is shaping up to be a good one, and we’re gearing up for a full lineup of holiday giveaways and seasonal fun to keep the momentum going into winter.
Your support and enthusiasm continue to give me life. Every photo, comment, and laugh reminds me why this community matters. So keep showing up, keep sharing your energy, and know that we’re building something special, mile by mile, together.
See you in The Driver’s Seat.
– Alex PlayOcto
October 2025
Dear Driver,
I want to begin this month with honesty. The launch of The Driver’s Seat did not unfold in the way I hoped. September was meant to kick off with a full calendar of “OCTivities,” but many of those plans never left the garage. The few that did roll out were underpromoted and, truthfully, underwhelming. Part of that was because my attention was pulled away by important matters outside of work, and I wasn’t able to bring the focus this role deserves.
I could promise that everything will be perfect going forward, but I would rather be real with you. Some months, the weight of the world makes it harder to bring the energy I want to give. Yet at the core of what I do is a simple purpose: to bring a little light, a little community, and maybe even a little fun into the lives of drivers who spend so much time on the road. That purpose is what gets me back behind the wheel, even when the drive feels uphill.
And this month, the road ahead looks exciting. October brings two big highlights for our community:
OCToWEEN 2025 is one of our longest-running traditions returns. Complete with the CARstume Contest where you can dress up your vehicle for the season and enter for a chance to win $500! This has always been one of my favorite community events, and I can’t wait to see the creativity you bring this year.
We’re launching the very first episode of our new livestream series, The J&J Pit Stop – presented by Hustler’s Hour. Hosted by two of our own car enthusiasts here at Octopus, this show will dig into mechanical tips, maintenance advice, and unique car features. It’s something fresh and practical, made by people who share your passion for the open road.
So while September may have been a stumble out of the gate, October has real momentum to look forward to. Thank you for giving me the grace to find my footing. I remain committed to making this community meaningful and worth your time. Together, I believe we can keep this ride moving in the right direction.
See you in The Driver’s Seat.
Alex PlayOcto
September 2025
Dear Driver,
For those of you who may not know me, my name is Alex, and I have been with Octopus since the very beginning. As one of the original members of the founding team, I have served as the face and voice of this business to our drivers from day one. Over the years, I have spent countless hours learning what matters to you, listening to your ideas, and carrying those conversations back to the other dedicated employees who build our product. At the same time, in return, I have asked for patience and grace as we worked through challenges and compromises over the years.
If you have been riding with Octopus for a while, you know our road has been anything but straight. We began as a scrappy startup, fighting for every green light. Over time, with determination and grit, we found our lane and eventually merged into something bigger than we ever imagined. With the support of our parent company, T-Mobile, along with our newer partnership through Uber, we now travel farther and faster than ever before.
Along the way, I have tried to design creative engagements to connect with our driver partners, not only to gather feedback but also to acknowledge something unique about rideshare life. While drivers meet dozens of people every day, the job itself can feel solitary. There is no water cooler or office breakroom to connect with like-minded co-workers. That is why I have worked to create various activities and promotions that break up that isolation and remind you that you are part of a larger community when partnered with Octopus.
That is also why I am excited to formally introduce: The Driver’s Seat. Think of it as your “breakroom”, a place to refuel with stories, contests, giveaways, meetups, and any other excuses we can come up with to have a good time (and give away some cash, of course!!). It may not feel like the old Facebook group at first, but with time, I hope it becomes a familiar place where you feel supported and connected.
This new chapter of social interaction will take time to find its rhythm, just as Octopus itself once did. It’s not perfect yet, but I am committed to making it worthwhile. My promise is to keep showing up with honesty and creativity, even when the road feels long. With your feedback and participation, we can chart a course that makes you proud and happy to driver with Octopus.
I want you to love this brand and be glad that Octopus rides with you. So fasten your seatbelts, and welcome to The Driver’s Seat. I am grateful you are here for the ride.
Sincerely,
Alex PlayOcto
