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Jesse Kay: How Gen Z can make entrepreneurship a lifestyle

Jesse Kay isn’t like most 19 year-olds. Kay is the Founder and CEO of Vyber Media, a digital marketing company that has had professional athletes, business executives, and other successful social icons as clients. He also hosts Trendsetters with Jesse Kay , formerly the 20 Under 20’s podcast, a show that focuses on entrepreneurship, aiming to inspire the next generation of business leaders. Since Kay started the podcast at age 16, he has gotten to interview the likes of serial entrepreneur Gary Vaynerchuk and Founder/CEO of Twitter & Square, Jack Dorsey.

It goes without saying that Jesse Kay leads a life very different from those of his peers. Growing up in an entrepreneurial home, Kay started his first business at age 9, when he began flipping sneakers on eBay.

Kay is a firm believer that Gen Z has the capacity to be just as, if not more, entrepreneurial than any of the previous generations. As he describes, growing up in a post-9/11 world and having experienced the recession at an early age, Gen Z has learned firsthand that nothing is given in life. In an age where as many as 85% of Americans “hate” their day job, Jesse Kay hopes to teach future professionals that there are options outside of the 9 to 5.

With this mission in mind, Kay started Trendsetters, beginning with 0 listeners, and no way of connecting himself with industry leaders. So, without any alternatives, Kay began cold-emailing roughly 350 people a day.

This strategy quickly landed him interviews with Gary Vaynerchuk, Grant Cardone, and other business magnates. He was able to land Jack Dorsey, who, after ignoring his invitation several times, eventually accepted when Kay joined his periscope live stream and continued to ask. His grit is admirable, to say the least.

Jesse Kay’s philosophy of never taking no for an answer ultimately brought him to a point in his career where Fortune 500 companies and professional athletes were asking him for help. With his skills and experience, Kay has helped numerous clients get their name out, and monetize their presence on social media. This, along with hosting a podcast that now garners upwards of 100k listeners every month.

What can budding professionals learn from Jesse Kay’s success?

Jesse Kay’s experience teaches Gen Z that they can get started with the careers of their dreams while they’re still young. A college student himself, Kay demonstrates that it’s possible to strike the perfect balance between business and academics. As a matter of fact, school might just be the perfect place for young entrepreneurs to begin along their paths.

Jesse Kay describes his inspiration for starting a podcast as coming from an “entrepreneurship” class he took in high school. At one point in the school year, he remembered hearing fellow students discuss potential business ideas. The only issue was that they had no clue how to take the first step in starting their endeavors. He thought, why not create a platform that inspires students to begin their own entrepreneurial journeys?

School, whether it be high school or college, is a fantastic place for fostering new ideas and approaches that can eventually turn into successful businesses. Educational contexts often serve as the breeding grounds for game-changing products and services. Often, students are told that their only purpose in school is to study and do well in their classes. What Jesse Kay’s success story tells, is that you’re never too young to begin pursuing your professional dreams.


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