Sydney & Jake first played together at a jam session in their native Tulsa, Oklahoma in December of 2013. Sydney had been living in Tulsa after graduating college at The University of Oregon. She was co-founder of a street band called The “S” Band that played early jazz, swing, and folk songs in the historic Brady Arts District in downtown Tulsa. The “S” Band’s efforts resulted in the creation of a busking scene in Tulsa that thrives to this day.
Jake was in town for the holidays visiting from Denton, Texas where he was working as a bandleader, composer, and private instructor following his graduation from The University of North Texas. The two exchanged numbers at that fateful jam session and kept in touch.
Dester once again visited Tulsa in the summer of 2014 and the two met up to play tunes and bonded over their shared love for many of the same songs and recordings. It was then, too, that their feelings for each other began to emerge. They stayed in contact, and over the next few months traveled back and forth growing together both musically and romantically.
In the fall of 2014, Jake, following a series of personnel shifts in his band, Feat Sauce, determined it would be best to move away from his college town to a larger city with a more consistent pool of musicians and greater stability. Having a couple of friends in Chicago, drummer Luke Angle and guitarist Lindon McCarty, who would have a room available in their apartment the next June, Jake got dibs on the vacancy and decided that he would try life in the city for a change.
In February of 2015, Sydney visited Dester in Denton on her way to New Orleans where she was going to meet up with an old friend, pianist and accordionist Clark McMahon, to perform in the streets during Mardi Gras. Jake, in the midst of a professional dry spell, opted to tag along.
The two spent ten days playing music together and exploring New Orleans. Staying with punks at a squat house, filling their bellies with po’ boys and beer, and running all around town soaking up the sights and sounds of Mardi Gras, their bond became even stronger.
In March of 2015, Jake moved to Tulsa to be with Sydney and try life in the same city together. If their bond strengthened, then they would move to Chicago together; if it weakened, Jake would move by himself. It turned out that being closer yielded great results.
While they both lived in Tulsa during the spring of 2015, they practiced music together and were active in the local jazz scene. Jake and Sydney regularly appeared at the Oklahoma Jazz Hall of Fame’s weekly jam session, and they frequently shared the stage with the city’s finest jazz artists, namely saxophonist Mike Cameron, and bassists Jordan Hehl and Dean DeMerritt.
Jake and Sydney moved to Chicago in the summer of 2015. They tried many different strategies to get work in the scene--including busking around the city--both together and separately, but the opportunities which they pursued were largely unfruitful. The period spent in Chicago soon became one of reevaluation and transition.
The two embarked on a quest for self-understanding as well as the understanding of personal development, business, and entrepreneurship spurred by the writings of Napoleon Hill and an online course by serial entrepreneur Tai Lopez. This time was spent shedding attachments and seeking new information from a multitude of books on management, psychology, entrepreneurship, self-improvement, and a myriad of other previously unexplored disciplines outside of music.
During this period in Chicago, Jake quit playing sax and exclusively sang and played guitar while Sydney put down the guitar and began playing bass. In this configuration, the two artists explored new instruments and the “new standards” from the 1950s on (from Sam Cooke to ABBA to Radiohead, they covered the covers).
One evening at dusk, while eating pizza on a rooftop near the coast of Lake Michigan, a pair of bats flew over their table. A friend yelled, “pizza bats!” and Sydney & Jake officially adopted The Pizza Bats as their band name. Sydney & Jake's first gig as The Pizza Bats was a fumbling hack through alternative rock covers, but, in time, the duo would build a skillful set of songs representing the greatest works from the past six decades.
Utilizing social media, running a YouTube channel featuring a new cover every week, and refining a system for learning and rehearsing repertoire, The Pizza Bats began building a sound (albeit a crude one at first), an image, and a brand. They hustled and landed gigs for their new configuration, adopting and applying the concepts they were now learning from the indispensable nonfiction works that they were adamantly consuming.
In February of 2016, following their regular gig at Irish Eyes Pub in Lincoln Square, the duo decided it was time to move to a more advantageous location. Study of the music industry had led The Pizza Bats to find that Chicago, while its music scene was undoubtedly filled with amazing talent, was clearly lacking in business connections, particularly in publishing and the like.
It was time, they concluded, to move to either Nashville, New York City, or Los Angeles. The pair ultimately opted for NYC (being carless since moving to Chicago), bought one-way plane tickets, spent a month donating, selling, or otherwise discarding their personal possessions, and, in March, Sydney & Jake landed in the city with nothing but “one carry-on and one personal item” each.
When they arrived in New York, they slept on floors and couches, in spare rooms and music practice rooms, and in hostels. Constantly at the mercy others, living by the generosity of friends, and unsure of when they would be asked to relocate, Sydney & Jake concluded that, though it wasn’t ideal, they would quickly need to find consistent jobs in whatever industry would have them.
Jake had bought a secondhand dobro and had been busking some, but income from playing in the subway was scant so he went to work as a cook in a busy Manhattan café. Sydney got a job as a cashier at a liquor store. The two eventually had enough combined income to secure more long-term shelter solutions.
A pair of brief subleases followed shortly after they found regular work. For a couple of months, Sydney & Jake scraped together their funds and eventually had enough to make a deposit on a longer-term agreement in a windowless, lofted bedroom in Bushwick which they affectionately dubbed “these batcaves”.
When they weren’t at work, their time was spent planning, studying, writing songs, and rehearsing new material. The duo performed around the area at such venues as Bizarre Bushwick, Bushwick Public House, Legion Bar, Wayward Social, and Terra Firma. They also spent a good deal of time busking during this period, playing their hefty set of covers on subway platforms off the L line.
By late summer of 2016, they were picking up steam and had a little money saved up so Sydney & Jake agreed that they would quit their jobs and pursue music full time. For several weeks, they focused all of their energy on the project, but they ultimately failed to secure enough income to be self-sufficient, and they went back to working jobs again.
Sydney now found herself as the office manager at a real estate company in Bushwick, and Jake--after multiple failed attempts to secure work teaching music--was employed full-time as a breakfast cook in a Williamsburg hotel.
Dester’s position in the hotel kitchen was largely subordinate: he spent the first three hours of his days my himself performing menial tasks such as plucking parsley leaves, zesting lemons, or separating egg whites from their yolks. After some time, in the midst of the mindlessness of it all, he began hearing bebop saxophone lines in his mind.
Although he had, while living in Chicago, denounced his identity as a saxophonist for a number of personal and deeply psychological reasons, he felt called back to the instrument by the musical ideas which now nagged him continually. In October of 2016, he borrowed a horn from a good friend and hit the subway platform to see what would come out.
Growth was slow at first, but feedback was highly positive. In time, Dester was making more money per hour playing sax in the subway than he was working as a cook. After an existential conversation with his supervising chef, he took the leap and quit his job at the hotel to busk full time. Soon after, he was getting hired to play gigs outside of the subway, and it didn’t take much to persuade Sydney to join him singing and playing guitar.
By November of 2016, Sydney & Jake had come full circle; they were a jazz duo once again, but now possessed a fresh perspective on their reality and dreams, their musical journeys, on business, and on life. Starting with just six tunes, the duo began playing in the subway at every opportunity. Money was good, and the higher level of musical expression afforded by the standard tunes and Christmas carols they were now playing was deeply refreshing artistically.
In January 2017, Sydney quit her job at the real estate office, and The Pizza Bats--now wholly convinced that they were on the right path--fought through the rest of winter in the chilly tunnels of the subway, developing a new set of songs and cultivating their unique sound. They have since made considerable headway and are now performing events throughout the city.
In March of 2017, the duo performed a benefit for the LGBTQ organization, Kaleidoscope Youth Center. In April, the band’s music was broadcast live on NYC’s WBAI 99.5FM. This June, the duo will be featured as a part of Make Music New York’s annual city-wide concert.
This May, the duo released (as The Pizza Bats) a 7-track album of jazz classics called Live at Bill’s Place, which is available on iTunes, Amazon, and Spotify.
In June, Sydney & Jake realized that The Pizza Bats had given birth to something new and that a new name was in order for their jazz duo pursuits.
They took the naming issue to social media, and after sifting through a long list of submissions, Sydney & Jake decided to call themselves Sydney & Jake for all jazz duo related matters.
Currently, the duo is focused on playing for private events throughout the New York City area, with the occasional public performances here and there.