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Spotlight on Jesse Kay

What inspired you to start your podcast, 20 Under 20s?

At the beginning of Junior year of high school, I was sitting in an “entrepreneurship” class. For the class, all of the students had to come up with a product or service and write a business plan for it. I realized that all of the students in my class were incredibly creative but had no idea how to execute on their idea. After seeing that, I decided to interview successful entrepreneurs and leaders that had done it themselves to help educate and inspire the next generation of leaders.


What has been your most memorable episode of the podcast, and why?

The most memorable episode of the podcast is my recent interview with Twitter and Square Founder/CEO Jack Dorsey. He is by far the largest guest I’ve ever had on the show. Also, I got him on from spamming a periscope he was doing asking him to come on the show in person… it worked!


Your first business was flipping sneakers on eBay at age 9. Do you see yourself moving into other entrepreneurial ventures in the future? If you do, what knowledge will you take from your podcast to apply?

Absolutely, that is what I’m doing now with my marketing work with small companies, influencers and fortune 500s. It’s been amazing getting to use the connections I’ve built from the podcast to grow deep relationships and even retain clients.


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