Claudia and Jackie Oshry, popular hosts of the podcast *The Toast*, recently shared insights about their personalities and experiences during an engaging live event in New York City. Taking place on May 16, the event was part of the Dear Media by Night series, where the sisters conversed about their lives, their hit podcast, and their connections with fans.
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*The Toast* has garnered a dedicated following for its unfiltered takes on a variety of topics, including pop culture and lifestyle trends. Known for their dynamic chemistry and relatable humour, the Oshry sisters have created an environment that allows fans to feel as though they know them personally. However, during their conversation with PEOPLE, the sisters revealed that there is much more to them than their lively on-air personas suggest.
As they stood before a responsive audience, Claudia and Jackie demonstrated their rapport by leading sing-alongs of their podcast’s theme song and even invited attendees to join in a spirited rendition of Miley Cyrus’s hit, *The Climb*. Their high-energy stage presence captured the spirit of the night, which aimed to celebrate the diverse talents of podcasters associated with Dear Media.
Despite their vibrant public appearances, Claudia, who is 31, admitted there is a quieter side to her character. “I’m more reserved in person. Online, I tend to portray a more extreme version of myself,” she explained. “People might expect me to be constantly entertaining, but I’m just a normal girl.” Jackie, her elder sister at 33, echoed this sentiment, declaring, “Many would be surprised at how shy we can be. We’re introverted extroverts, really.”
The evening featured an impressive lineup of fellow podcasters from Dear Media, including Amanda Hirsch, Josh Peck, and Claudia’s husband, Ben Soffer. Together, the event celebrated the close-knit community that has emerged within the podcasting realm, something the sisters find particularly rewarding. “Working alongside our fellow hosts is a fantastic experience, especially since we don’t get to see them often,” Jackie noted. “Being part of this larger group and enjoying each other’s content makes for a wonderful entertainment night.”
Claudia also addressed the unique aspect of working alongside her family, with both her sister and husband by her side. “For some, it’s hard to imagine working so closely with family, but for us, it’s the best gift. We share an incredible work-life balance and have the opportunity to do extraordinary things together.” Jackie added, “People often ask how we can work with family. I wonder, how do people do it without their family?”
On social media, Claudia has made quite an impression with 3 million followers on Instagram as @girlwithnojob, a username that catapulted her to fame even before launching *The Toast* in 2018. Jackie, on the other hand, boasts 365,000 followers and describes herself on social media as the “Founder and CEO of Turdy Lou Global,” referencing a shared inside joke that resonates with their audience. Claudia recently displayed her talents to an even broader audience when she appeared on the 14th season of *The Masked Singer*, although she surprised viewers by choosing to voluntarily exit the show.
Michael Bosstick, CEO of Dear Media, expressed admiration for what the Oshry sisters have accomplished in blending their online presence with real-world engagement through events like Dear Media by Night. “Our audience is incredible, and we want to create opportunities for them to connect in person, having fun both online and offline,” he shared. The success of the event exemplifies how the Oshry sisters are bringing their followers into the fold of their lives, fostering community and shared experiences.
Overall, Claudia and Jackie Oshry continue to entertain and connect with their audience, revealing a complex blend of humour, authenticity, and closeness that resonates deeply with fans. As they navigate their careers in podcasting, their journey exemplifies the evolving landscape of media and the importance of real-life connections in an increasingly digital world.