Jon Cattivera and the work that outlasts the show

The tour dates were late. At Sessions, where Jon Cattivera worked in the record-label department, a band’s website might get updated only a week before the musicians left town. Sometimes it did not happen at all. For someone trying to get people to a show, this was an awkward arrangement. The audience needed to know where to turn up. The website appeared to be keeping its options open.

Cattivera learned to handle the updates himself. The label needed artwork, advertisements and posters, too, while the company’s art department had an apparel business to attend to. Design entered his working life through a queue of things that needed doing. It came with a deadline and people he knew.

Today he is the founder and CEO of Sleepless Media, the agency he began in 2003. He is also the singer, guitarist and songwriter of Time Spent Driving. Those two descriptions have shared a biography for years. The interesting question is how he has kept making room for both.

A website, a deadline, a $600 computer

Before Sessions, Cattivera worked at Peet’s on Pacific Avenue in Santa Cruz. A volunteer position in the label department offered a way into a world he already cared about. It became a full-time job in sales and marketing, with the design work accumulating alongside it.

When the department downsized, he bought a $600 Dell, set up in his living room and emailed his contacts. He called the business Sleepless Design, then Sleepless Media, after the hours he spent working. Early websites included projects for Washburn Guitars and Santa Cruz skate, snowboard and surf brands.

By the agency’s fifteenth anniversary in 2018, Cattivera described a staff of about twelve and hundreds of completed websites. The business had moved from the living room to Pearl Alley, then the Old Sash Mill and later 41st Avenue. Each address marked the same small problem becoming a larger operation. He credited local clients for helping him make a living in the place where he grew up, and for making that possible for his employees, too.

The practical overlap is easy to see. A musician understands why a show announcement matters. Someone working around skate brands knows that the artwork belongs to the product’s appeal. His first business relationships grew around interests he already had. The contact list preceded the company.

Sleepless Media now describes a team working remotely across the United States. Its current roster includes designers, developers, project managers and strategists. Cattivera is listed as founder and CEO; Leslee is creative director. The agency’s Shopify Plus work places it in the detailed business of helping brands sell online. The job has grown beyond the original band-site problem, with more people needed to do it.

Before the business, a badminton partnership

There is an earlier origin story, with less commerce and more shuttlecock. Cattivera and future bandmate Derek had attended school together since fifth grade. They became friends around their sophomore year, when they were partners in P.E. badminton. In Cattivera’s recollection, their record was formidable. Rock history is usually more interested in the guitars.

His father had given him one for Christmas, without being asked. Derek knew a few songs and taught him material by Bad Religion and Nirvana. They started a punk band and improved together. Eventually, after earlier groups, they began the project that became Time Spent Driving. When a separate singer proved elusive, Cattivera took the microphone.

His musical education also happened through skateboard videos, zines, record sleeves and other people’s recommendations. A band named in a thank-you list could lead to another record. A sticker on a drum kit might be enough reason to investigate. Black Flag’s In My Head was an early record that pulled him further into punk.

That is a wonderfully particular way to learn: follow the small clue someone else left behind. It demands curiosity and a little effort. Before recommendations arrived automatically, a listener could make an evening’s research out of the inside of a CD case.

The art of staying together

Time Spent Driving released Just Enough Bright in 2002, with J. Robbins producing. Touring took the band around the United States and Europe; its music also appeared in video games. There was momentum, followed by the ordinary difficulties that can stop a group: personnel changes, distance and a schedule that became hard to sustain.

Cattivera continued playing. His musical life included Crucial Unicorn and Gentlemen of Japan, as well as a Fury 66 reunion. When Time Spent Driving returned in 2012, he already had years of running a studio behind him. The reunion entered a different calendar from the one the original band had known.

By 2020, he was describing a slower approach. Fewer rehearsals and less pressure to tour made staying together more practical. Work that once took months could take years. That trade allowed the group to continue around jobs and families. Passed & Presence arrived in 2015; Estrangers, Vol. 1 followed in 2020, ahead of the full album in 2023.

A slower release schedule can look uneventful from outside. Inside a band, it can contain writing, arranging, replacing a member and finding a date when everyone is available. The audience sees the record appear. The musicians have also had to keep the group possible.

A demo is where the argument begins

Cattivera writes and demos complete songs, including the lyrics, before the other musicians work on them. Having the shape ready helps the group move. It also creates something he has invested in before anybody else has offered an opinion.

He welcomes their editing, even when it requires letting go of an idea. The band can hear what he has become too attached to. Long experience together makes the discussion easier, though familiarity also means anticipating everyone’s reaction before they have heard the song.

“I want to create and put things out into the world.”

Jon Cattivera

Even building that shared vocabulary involved some gentle persuasion. When drummer Kem joined, his reference points were closer to mainstream rock. The others gave him CDs for Christmas to introduce the records informing their sound. A gift can be both generous and a politely wrapped artistic suggestion.

Cattivera’s advice to his younger self has included learning to record and mix earlier. He has also spoken about easing up on ego and taking things less seriously. These are useful ambitions for someone whose work repeatedly goes through other people’s hands. A song may start privately. Finishing it requires company.

The woods get into the work

In the Santa Cruz Mountains, the landscape has become part of Cattivera’s visual vocabulary. The video for “Intents and Purposes” was filmed on his property. He described wanting its colors and contrasts to create a deliberately surreal appearance. The surroundings supply recognizable details, while the treatment gives them another atmosphere.

There is also Breathing Trees, his outdoor accommodation project with cabins and a treehouse. Tree Tents USA’s team page lists him as USA partner and executive director, leading its North American division. The company makes small outdoor structures, bringing another form of design into his working life.

The connections are unusually tangible. A place can become a setting for a video, accommodation for a visitor or an occasion to think about how something is made. In each case, there is an experience to arrange. The scale changes from a screen to a room suspended among trees.

There is another record to make

Lost Leaves arrived in August 2026 through Thirty Something Records. Much of its writing happened between October 2022 and January 2023, before Estrangers had been released. Home recording and file sharing helped the musicians develop parts without waiting for every idea to be worked out in one room.

The new music also makes room for old friends. Chris Wicky of Favez contributes vocals to “The Red Dress.” On “She’s the One,” Marc Allen supplies high harmonies. Meanwhile, the band has returned to Just Enough Bright with Robbins, whose new mix accompanies its vinyl release. The back catalogue and the next record are occupying the same present.

In October, Cattivera was discussing prospective shows, more demos and a planned seven-inch. He had also hosted acoustic performers at Breathing Trees and was considering more music there. A song, a gathering and a place in the woods can all generate another project. The practical question remains when to fit it in.

For a smaller glimpse of his appetite for independent judgment, consider pizza. His preference is pepperoni and pineapple, perhaps with jalapeños. He has defended it with cheerful confidence. After years of making work that other people will have opinions about, choosing his own toppings seems a reasonable privilege.

His careers keep producing specific things: a website someone can use, a recording someone can play, another arrangement to finish. The band website that once needed attention has become a long working life with several open files. Somewhere in the schedule, there is still another song.