Jun 2, 2025
Jourden Skillman
Founder
Every business evolves. Sometimes it’s gradual. Other times, the shift is clear, intentional, and overdue. This is one of those times.
We’ve transitioned from Eighth Avenue to Optimistic—a name and direction that better reflect our purpose: helping teams run smarter, smoother, and more sustainably. Our work is no longer limited to local small businesses, though they’ll always have a place here. Today, we support founders, creative agencies, cross-functional teams, and growing businesses of all kinds—teams who want systems that work with them, not against them.
Whether you’ve worked with us before or are just getting to know us, this is the story behind the shift—and where we’re headed next.
The Early Days
For several years, Eighth Avenue was our home—named to reflect a place of endless opportunity, open-ended paths, and the creative energy we brought to every project. Our core offerings included web design, web development, and reliable ongoing support. Most of our clients were small businesses and creatives who needed websites that were both functional and thoughtful—easy to manage, built to last, and designed with intention. Our web management services kept things updated, secure, and aligned with clients’ changing needs. It was work grounded in service, consistency, and long-term support.
Looking back, that chapter laid the foundation for everything we’ve built since. As our experience deepened, so did the quality and clarity of our work. We refined our processes, raised our standards, and started thinking more holistically about how everything fit together—from strategy to delivery to daily operations.
Over time, we began to notice a common thread—what clients needed most, and where we naturally did our best work. Clients started asking about our internal systems: how we stayed organized, how we managed projects, how we kept things moving. They wanted to apply the same structure to their own businesses—to improve their revenue, client experience, and day-to-day operations. That became the missing piece—and the work we’re now most excited to lead with.
More Than a Name
Optimistic isn’t just a rebrand—it’s a reflection of what we believe work can be.
We chose the name because it captures what we’re working toward with our clients: a more optimistic future, where businesses run more smoothly, teams feel supported, and leaders get to focus on the things that matter most—whether that’s growth, creativity, family, or simply having more space to breathe.
At the heart of Optimistic is the Optimistic OS—a systems-first operating framework designed to help teams reduce friction, increase clarity, and scale sustainably. But it’s not just about getting organized. It’s about creating the conditions for profit, momentum, and leverage.
We empower our clients to:
Increase clarity and reduce confusion across projects
Save time through repeatable, automated workflows
Improve margins by tightening up delivery systems
Strengthen client experience with more consistent, predictable results
Scale operations without burning out the team
The goal isn’t just better systems. It’s more freedom, more capacity, and more energy to invest in the work, and life, that you care about.
Introducing SmartOps+
While operations is now our core focus, we haven’t left our creative and technical roots behind. Our foundational subscription, SmartOps+, is designed to support and evolve the systems created during the Optimistic OS program. It’s the ongoing layer that keeps things running—refining workflows, providing hands-on support, and helping teams stay focused, clear, and flexible as they grow.
We still offer web design, web development, and ongoing web support as add-ons to SmartOps+. Each service includes access to prebuilt workflows and delivery systems—plug-and-play, managed by Optimistic, and designed to extend your in-house capacity without added stress. It’s a high-value, flexible way to get fast, consistent results without sacrificing quality.
In addition to web services, we’ve expanded our add-on offerings to support the broader needs of growing teams:
Project Management
Get a dedicated project manager—trained by Optimistic—to help run your internal systems. They act as a second brain, bringing structure, follow-through, and visibility across the business.Content & Creative
Photo, video, social media, and creative strategy—delivered in alignment with your brand and backed by systems that ensure it gets done consistently.Graphic Design
Clean, on-brand visuals to support campaigns, assets, and internal needs—available on retainer for flexible access.Web Design & Development
Whether it’s Framer, Webflow, or something custom, our design and dev work remains thoughtful, flexible, and integrated into the bigger picture of your operations.Data Visualization & Analytics
We help you track what matters—turning data into dashboards, reports, and real insights you can actually use to make decisions.
By combining SmartOps+ with these add-ons, our clients get the systems, support, and creative execution they need to move faster—with less friction and more clarity.
You can view all current plan and add-on options here.
Conclusion
For us, Optimistic is more than a name. It’s a mindset. A direction. A quiet confidence that work can feel better—lighter, more intentional, and more aligned with the life you’re building outside of it. We’re committed to being more than consultants. We’re collaborators. Problem-solvers. System-builders. Thoughtful partners who want to make work feel like play.
We’ve seen firsthand how better systems lead to better outcomes: not just more revenue or efficiency, but more clarity. Less time wasted. Fewer dropped balls. More confidence in where you’re going and how you’ll get there.
And that clarity unlocks something powerful: freedom. Freedom to step out of the weeds. Freedom to grow without burning out. Freedom to focus on the work you love—and the life you want to live alongside it.
That’s the future we’re building with our clients. A more optimistic one, where work feels like play, and success doesn’t come at the cost of your energy, time, or values.
Thanks for being part of our story so far. We’re excited for what’s ahead.
