From Concept To Finished Poster With Iconfactory

June 6, 2025

Show poster for 'James Dempsey and the Breakpoints, LIVE near WWDC 2023, a benefit concert for Techtonica'. A view of Santa Clara valley, mountains in the background with Apple Park off in the distance. In the foreground a Tiki outpost with a ukulele.

We started creating posters for LIVE near WWDC shows back in 2017.

Each year, we try to use a different style. Some years the posters have been created by talented artists, some years it’s just been me.

I’ve always admired vintage national parks posters done by the WPA in the 1930s. I came across the SimpleBits font Parkly, which is inspired by those posters, which in turn inspired me to go with that style this year.

I could picture the end result that I was hoping for but knew I definitely did not have the artistic skills required to create what I had in mind.

On Mastodon, I asked for recommendations for real human artists (thanks to everyone who replied!). One of the replies was from Cheryl Cicha at Iconfactory.

Iconfactory is a legendary design house, having created icons and app designs for many well-known apps, as well as their own apps, for more than a quarter century.

Without Cheryl’s reply, it would not have occurred to me to approach Iconfactory for a show poster. In my mind they were strongly associated with icons and apps.

Even after her suggestion, there was a little anxiety on my part. It’s probably a bit of imposter syndrome on my part, but our yearly benefit concert is a small operation in the grand scheme of things.

Should I be dreaming about having a show poster created by a company with some of the most talented designers and artists in the business?

In the end, it was a pleasure to work with Iconfactory and I am incredibly happy with the results. The answer to my question has turned out to be an enthusiastic ‘Yes!’.

From Concept To Poster

The process of working with the folks at Iconfactory was very collaborative, exploring a number of ideas in a relatively short period of time.

The artist for the poster is Anthony Piraino, who was familiar with this artistic style and happened to already have prints of a few of those national parks posters in his office.

Show poster for 'James Dempsey and the Breakpoints, LIVE near WWDC 2023, a benefit concert for Techtonica'. A view of Santa Clara valley, mountains in the background with Apple Park off in the distance. In the foreground a Tiki outpost with a ukulele.
My original concept sketch.
An awful piece of artwork—but it got the point across.

I provided a very rough concept sketch and a few pages of notes and Anthony did a first pass at the artwork.

It was a very iterative process. I provided feedback and suggestions based on work in progress. Anthony made suggestions and many design choices, and we puzzled out a few design questions together.

Turnaround was quick incorporating feedback.

Comparing the original concept sketch to the final poster, two things occur to me.

The first is that despite being an awful piece of artwork, the concept sketch managed to convey what I had in mind.

The second is that Anthony did a fantastic job of taking that sketch and many, many notes and ideas of mine and incorporated them into a beautiful piece of artwork.

LIVE near WWDC

This is the first show poster to visually represent the name of the concert: LIVE near WWDC.

The official event is happening off in the distance at Apple Park while our own joyous band of nerdy musicians performs nearby.

The Tiki outpost is inspired by the venue for the show—local San Jose geekeasy The Art Boutiki.

The Santa Clara Valley, better known as Silicon Valley, is depicted with a nod to its past, filled with greenery, as opposed to highways, strip malls, and tech company campuses.

Easter Eggs

The poster also includes a few visual easter eggs.

First, every piece of JDBP album art and every show poster includes the breakpoint symbol in one form or another. Sometimes it is fairly obvious, sometimes much more subtle. This year it appears in two contexts, not particularly hidden.

An Xcode breakpoint.

The Breakpoint symbol itself is inspired by how a breakpoint is represented in Xcode. Other IDEs may use different visual representations, but we’ve been pretty happy with this shape and variations of “breakpoint blue”.

Besides the breakpoint motif, the poster incorporates a few additional easter eggs. One stands out to longtime Mac users pretty quickly. The other two are more subtle. No spoilers in this post, but I may post a few hints on Mastodon over the next few days.

Posters Available At The Show

It is always an exciting day for me when the show posters arrive from the printer.

Show poster for 'James Dempsey and the Breakpoints, LIVE near WWDC 2023, a benefit concert for Techtonica'. A view of Santa Clara valley, mountains in the background with Apple Park off in the distance. In the foreground a Tiki outpost with a ukulele.

The printed posters provide tangible evidence, beyond fleeting Mastodon messages, blog posts, and the like, that the show is on its way.

Show posters will be on sale at the event with all proceeds going to the show beneficiary, Techtonica. If you‘re a VIP ticket holder, we already have you covered, one is included with your ticket.

To help raise funds for Techtonica, a very limited number of posters signed by me and all of the Breakpoints performing at the show will also be available.

We provide a hard cardstock envelope for the poster so you can mail it, put it in luggage, etc. and guard against the poster being bent or damaged.

Some Tickets Still Available

The show is getting very close to being sold out, but some tickets are still available.

If you have been planning on coming to the show but have not gotten around to buying your ticket yet, this would be the perfect time.

And if you can’t make it to the show, you can watch the live stream of the concert.

Show and live stream details and tickets sales are at livenearwwdc.com

I hope to see you Wednesday night for LIVE near WWDC 2025! •


You can always find the latest news about LIVE near WWDC at https://livenearwwdc.com.

Our sponsors make this show possible. Everyone involved in this event, from planning to performing, sends an enormous thank you to our sponsors for their support. Please support our sponsors by clicking through the links below and checking them out!

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Categories: Apple, Mac, Music, Software Development, iOS

Tags: Apple, Apple Worldwide Developers Conference, Breakpoints, Design, JDBP, James Dempsey, James Dempsey and the Breakpoints, LIVE near WWDC, Mac, Software Development, Ukulele, WWDC, WWDC 2025, WWDC25, iOS, macOS, music