Kaiser grew up in Santa Clara, California, and began competitive karting as early as 2003, competing in the International Kart Federation through 2009. He won his first national championship in the HPV-1 class in 2008 and claimed the Infineon Raceway 3-hour Karting Enduro in 2009. His early formation included the Skip Barber Racing School Western Regional Championship, where he earned second place and Rookie of the Year in 2009/10, and returned to finish third in 2011. Alongside his racing commitments, Kaiser has been enrolled part-time at Santa Clara University.
In 2012, Kaiser competed in the Formula Car Challenge with World Speed Motorsports, winning the Pro Mazda class championship with eight race victories and eleven podium finishes in fourteen races — establishing him as a dominant junior-formula talent.
He made his professional open-wheel debut in September 2012 at the Star Mazda Championship at Mazda Raceway Laguna Seca. For the 2013 season, he joined World Speed Motorsports full-time in the Pro Mazda Championship, finishing seventh with a best result of fifth place. He switched to Juncos Racing for 2014 and claimed his first professional victory at Sonoma Raceway in the season finale, finishing sixth in the championship with four podium finishes. The move to Juncos would define the next chapter of his career.
Kaiser stepped up to the Indy Lights series with Juncos Racing in 2015. Over his first season, he recorded two podiums and seven top-five finishes in sixteen races, ending sixth in the championship. He returned in 2016 with greater pace, securing two race wins and eight podiums in eighteen starts to finish third overall.
For 2017, Kaiser contested his third consecutive Indy Lights season with Juncos Racing. The campaign proved decisive: he won the championship outright and claimed the associated one-million-dollar scholarship granting entry to the IndyCar Series. The title capped a three-year development arc at Juncos that had steadily elevated his results year on year.
Kaiser made his IndyCar Series debut with Juncos Racing in 2018, competing in four events. He remained with the team for select appearances through 2019, including his most prominent moment in the sport.
At the 2019 Indianapolis 500, Kaiser secured the final spot on the starting grid, qualifying ahead of Fernando Alonso — a two-time Formula One world champion racing under a joint McLaren and Carlin effort. Alonso failed to qualify for the race after being edged out, an outcome that drew considerable international attention. Kaiser's performance in claiming that last grid spot was widely regarded as one of the more notable qualifying upsets in recent Indianapolis 500 history.
Kaiser did not compete in either the 2020 or 2021 IndyCar seasons, as Juncos Racing — rebranded as Juncos Hollinger Racing after the arrival of co-owner Brad Hollinger — focused financial resources on establishing a full-time entry. The team selected Scuderia Ferrari test driver Callum Ilott for their full-time 2022 program, though they did not rule out bringing Kaiser back in a second car on a part-time basis, including for the Indianapolis 500.
Kaiser's career represents a compact but noteworthy trajectory through American open-wheel racing. His 2017 Indy Lights title remains his highest competitive achievement, and his role in eliminating Fernando Alonso from the 2019 Indianapolis 500 field ensured his name entered broader motorsport conversation. His association with Juncos Racing across multiple categories forms the throughline of his professional career.
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