Make every word count.
That's what I'm thinking about when I design a product—in this case, my application to join 37signals. Whether I'm crafting a UI or writing copy, I see it as my responsibility as product designer to deliver what you came here for, without wasting your time.
So let's get right to it.
Having designed and shipped my own products to thousands of customers, I know what it means to take ownership of a product, from concept to launch and iteration.
Bootstrapping my business over the last 18 years required me to pick up more skills than my core craft of designing in browsers with HTML and CSS.
Writing. Programming. Customer support. Hiring. Video production. Branding... I almost typed 'marketing', but if I'm honest, I believe that a product designed with care and respect for its users is the best marketing there is.
It's been 20 years since I sought employment at a company that's not my own. So why start now?
I see this opportunity both as a perfect fit for my skills and experience, and a totally new challenge that could define my next chapter.
The fit: The 37signals way of working—asynchronous collaboration, a focus on shipping and a commitment to the craft—have been my natural way of operating for my entire career. The chance to deepen this approach with the industry's best product team would be a total thrill.
The challenge: While I'm not new to team environments (I've hired and managed small remote teams for years), taking off the business owner's hat to focus on my sweet spot—bringing product ideas to life—will be a gear shift, for sure. But the chance to work alongside the team I've admired for years, helping shape products at a new level of scale? That makes the whole "unemployable" thing just feel silly. Let's go.
Here's the highlight reel of some of my favorite work from the past few years.
An async video messaging product. Designed and built by me and 1-2 backend Rails developers. I started it in 2021, and currently maintain it with 1 support person and 1 dev.
A UI components library for Ruby on Rails. Designed to make shipping polished apps with Rails and Hotwire easier and faster. I'm actively working on it now, aiming to launch in Q2 2025.
My full stack product design offering, positioned as a productized consulting service where I work with founders to build and ship their V1 SaaS product in a month.
I designed and built this podcasting platform in 2024 aimed at connecting podcast audiences with eachother. It didn't work as a business but I'm proud of the product (and still use it!).
I co-hosted the Bootstrapped Web podcast for 10 years and recently launched a new show, The Panel, with co-host Justin Jackson where we talk products, business and life!
This year I'm showing my product work on my YouTube channel where I try to emphasize striking a balance between attention to detail and shipping fast.
My personal blog is where I write about my journey and craft over the course of my career as a product designer and business owner.
2 things come to mind when I think about what inspires me professionally and creatively:
The first is something Adam Wathan recently said: When describing his ideal company, he made the analogy to the experience of playing in a band. That resonated with me—not just because I'm a lifelong musician and songwriter—but because I get fired up by seeing small, high-caliber teams shipping products that reflect their taste. 37signals and Tailwind Labs are two shining examples of that.
The other (and sorry if this is a little corny), but my daughters (8 and 11) inspire me in ways I never could have dreamed of earlier in my career. Two specifics come to mind:
I don't know where in the stack of applications mine will end up. But if we get the chance to meet, I would be thrilled to learn more about the possibility of working together.
Either way, I'm glad I stumbled onto this opportunity (heard it on your podcast!). Preparing this letter and site was a worthwhile project in itself.
Keep up the great work!
Brian Casel
[email protected]
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