Liquid Glass: The Song

September 5, 2025

In advance of the fall OS releases from Apple, I wrote a little song about Liquid Glass.

It’s a short ditty, only about 90 seconds long. I hope it will bring a smile.

The song came together very quickly, written in the morning, performed for the first time that evening. I’ve included that story below the video.

Please feel free to share it with others who might enjoy it as well!

Making of a Song: 12 Hours and 1200 Miles

The song was conceived, written, and debuted over a 12 hour period while on my way from Anaheim, CA to Seattle, WA.

I started the day at Disneyland—a typical post-WWDC destination for me. I was about to embark on a day-long journey to Seattle to play a few songs in a mini-Breakpoint Jam at Brent Simmon’s retirement party.

The idea for the song hit me as I was walking across the grounds of the Disneyland Hotel, roller bag in tow, heading for the airport.

Once I got through security, I found an empty gate, and worked out the chords on my ukulele. I also recorded the ukulele part so I could ‘practice’ silently in my head on the flight.

I had a 90-minute layover in Oakland. I texted longtime Breakpoint Laura Savino, who was performing with us that night. I sent her the chords and she kindly agreed to print out a chord chart for the new song.

I arrived in Seattle, checked into my hotel and ran through the song a couple of times in my room.

Omni Group CEO and Breakpoint Ken Case was also performing with us that night. He was also good enough to give me a lift to the show. I gave him a preview of the song in the car en route. Fortunately he was amused, so it seemed the song was on the right track.

Audio Version Of The Song

In the coming days I will be making an audio version of Liquid Glass available to everyone on the James Dempsey and the Breakpoints mailing list. This low-volume mailing list also gets early access to tickets for our annual LIVE near WWDC show.

If you’re interested, please join the mailing list! •


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

Where I’ll be at WWDC 2025

June 9, 2025

I’ll be doing a few things this week at WWDC25 and wanted to pass along my schedule. Hope to see you at one or more of these happenings!

Tuesday: Fireside Chat with Michael Darius at One More Thing

One More Thing Conference Logo
On Tuesday morning at the One More Thing conference, I will be interviewing former Apple designer Michael Darius.

This session will feature the premiere of “King of Cupertino”, a musical tribute to Steve Jobs.

The fireside chat will focus on Michael’s reflections on the spiritual nature of development.

You can RSVP for this session.

One More Thing, June 9-12, 2025
Fireside Chat with Michael Darius, Tuesday, June 10th
10:30 AM Pacific

Wednesday: LIVE near WWDC 2025

James Dempsey and the Breakpoints JDBP Logo
On Wednesday night James Dempsey and the Breakpoints perform LIVE near WWDC in a benefit concert for Techtonica.

The show is a full concert of humorous, original, programming-oriented songs, including favorites from our iTunes chart-topping, #5 Billboard comedy album Backtrace.

I’ll be joined on stage by the Breakpoints—a fabled group of talented techies-by-day and musicians-by-night who make the music and fun come alive!

You can enjoy the show in person or watch the free live stream.

The live stream includes a live chat hosted by Breakpoints Steve Hayman and Tom Harrington. Join the live chat to connect with other folks in the community while enjoying the show!

Full details are at livenearwwdc.com.

James Dempsey and the Breakpoints, LIVE near WWDC
Wednesday, June 11th
Doors open at 7:00 PM Pacific, Music starts about 8:00 PM Pacific
Live chat starts at 7:30 PM Pacific

Thursday: WWDC25 Week In Review at One More Thing

One More Thing Conference Logo
Continuing a tradition that started at AltConf, I’ll be closing out the week at the
One More Thing conference with a WWDC Week In Review, a lighthearted look back at the announcements and events of the week.

After a week front-loaded with announcements and technical talks—this easy-going closing session of One More Thing combines humor, music, and perspective.

And there will be a bit involving a ukulele.

The closing party for One More Thing will be held immediately after the session. So come on by, enjoy the session and then the party. RSVP for the event.

One More Thing, June 9-12, 2025
Closing Session, Thursday, June 12th
3:30 PM Pacific

A Busy WWDC25 Week

As usual, it will be a busy WWDC week with plenty of new announcements and technology to wrap our heads around. Feel free to follow me on Mastodon and say hello!

I hope you can make it out to one or more of these events—see you at WWDC! •


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

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!

Platinum Sponsor

Gold Sponsors

Silver Sponsors


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

LIVE near WWDC 2025 Livestream

June 4, 2025

I am very happy to report that we’ve worked out the details and will be livestreaming the LIVE near WWDC show once again this year.

If you’re not going to be in town for WWDC (or could not get a ticket to the show—they’re going fast!) you’ll be able to watch the show from wherever you happen to be.

There will be a live chat along with the stream before and during the concert, hosted by Breakpoints Steve Hayman and Tom Harrington. The live chat is a great way to connect with other members of the community.

The live chat begins at 7:30 pm with the music starting about 8:00 pm. All times Pacific.

The live stream is free, no paywall or ticket required to watch the concert online. In the spirit of the benefit concert, we do request you consider making a donation to Techtonica.

Tickets still available

A limited number of tickets are still available to come see the show in person.

Tickets and full show info are available at livenearwwdc.com.

Whether you attend in person or watch the livestream, we hope you can join us on Wednesday, June 11 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!

Platinum Sponsor

Gold Sponsors

Silver Sponsors


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

LIVE near WWDC 2025

May 30, 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.

It’s that time of year where rumors fly in anticipation of another WWDC keynote.

Meanwhile across multiple timezones, Breakpoints are rehearsing nights and weekends getting ready to perform LIVE near WWDC once again.

For 2025, the show returns to The Art Boutiki—a funky San Jose gem of a venue and self-proclaimed “Geekeasy”.

(Being a sucker for a nice pun, when scouting venues last year, they pretty much had me at “Geekeasy” before I even walked in the door.)

Carrying on what has become a yearly tradition, this year’s show poster is inspired by vintage National Parks posters of the 1930s. It leans into the theme of the venue and the name of the show, with a Tiki outpost near, but not at WWDC, with Apple Park in the distance.

The poster art was created a talented artist at the legendary Iconfactory. They were a pleasure to work with as we iterated on the design, moving from a truly terrible rough concept sketch and a few pages of notes I provided to the finished artwork. I am very happy with how the poster turned out and am looking forward to hanging it on my wall.

Show posters (11” x 17”) will be on sale at the event with all proceeds going to Techtonica. If you‘re a VIP ticket holder, we already have you covered, one is included with your ticket.

You can get tickets to the show as well as full details (date, time, venue address, etc.) at livenearwwdc.com.

Tickets are still available but they have been going quickly.

Every year I hear from people who waited to buy tickets and then were disappointed that the show was sold out. If you are planning on coming to the show, I encourage you to get your tickets now to save yourself a lifetime of regret. ;)

Introducing A New Song

At the end of April, at the Deep Dish Swift conference, I performed a new song as a work in progress. I had arrived in Chicago on Saturday afternoon with a partially-written song with a chorus and bridge but no verses at that point. By noon on Monday, I had a completed draft of the full lyrics and melody. Between conference sessions I would rush back to my room to rehearse the new song for our Breakpoint Jam on Tuesday afternoon.

Because it was brand new, there wasn’t time to have the other performers learn it, so it was just me singing and playing ukulele. On stage, I called it the TestFlight version of the song because just like an app in TestFlight, it wasn’t the final version and the entire thing could potentially come crashing down at any moment.

We’ve been working on the arrangement for the full band and are really looking forward to sharing it everyone live at the show.

The Band

Speaking of the band, as in past years, we have an eclectic group of musicians ranging from the core band of drums, bass, rhythm and lead guitars to violin, banjo, saxophone, Croatian tamburica—and of course: slide-advance keyboard; additional vocalists round out the sound.

At present about 18 different musicians are expected to perform, arriving in the Bay Area from various locations around the globe. The exact lineup is always subject to change right up until showtime. This year, we have a mix of longtime Breakpoints as well as some folks performing LIVE near WWDC for the first time.

I am incredibly grateful to everyone who lends their time and talent to the show. This includes all of the musicians as well as folks volunteering to do operations like working the door and the merch table, photographing the show, and producing on the livestream.

For me, one of the greatest joys of this band has been the number of people I have had the chance to meet, get to know, and perform with over the years at various LIVE near WWDC shows and Breakpoint Jams. This community has so many wonderful, talented people and it has been a true honor to have so many join me on stage.

A Big Night During A Big Week

WWDC25 is promising to be an exciting week full of announcements and almost certainly some surprises.

And for Wednesday, June 11th, we‘ve been working on a show we hope you’ll really enjoy.

Once again, all of us are incredibly excited and grateful to be able do this show again; happy to be supporting Techtonica; and very thankful for the support of our sponsors.

We all hope you can join us on Wednesday night for LIVE near WWDC 2025! •


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

And speaking of sponsors—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!

Platinum Sponsor

Gold Sponsors

Silver Sponsors


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