Jesse Kay - How An 18-Year Old Got To Interview People Like Jack Dorsey And Gary Vaynerchuk - E.127

April 2, 2019

How does an 18 year old get to interview the likes of Gary Vaynerchuk and Jack Dorsey?


He starts early and sends 350 emails a day.


Jesse Kay started his entrepreneur venture when he was 9 years old when he started flipping shoes on eBay. Which led to starting the podcast at 16. When you send 350 emails, someone is going to respond, and as they started to pile up, it lead to internships and relationships that allowed him to grow his own media company.

Now he helps mainly athletes with their social media growth and finding ways to monetize their audience on social media. 


How do you interview the best of the best?

  • Send 350 emails a day, yea it sounds like a lot, but when you’re first starting out and don’t have a reputation to go off of; that means you have time to spend to build that reputation

  • Find a differentiating point. Jesse used that he was a 16 year old podcast host, what's your differentiating point?

  • Go into it to build a relationship, not a one and done thing where you get an interview and thats that

How to build legitimacy, especially when you’re young?

  • Start off with one client, make sure you give him more value than they are paying you

  • Referrals, referrals, referrals

  • Find your way in, for Jesse it was getting people onto the podcast and then he shows people what they do

  • Give free advice and give them as much advice as possible

When you hear Jesse talk, it seems like he’d be an extrovert and someone who has always been open to talking to people on a regular basis, but it was actually the complete opposite for him growing up. He had severe anxiety and the best way he found to cope with it was putting himself in situations where he couldn’t back out. For example his first ever speaking engagement was on stage with Gary Vaynerchuk in front of a thousand people… 


Jesse preaches a message of being consistent with your actions, putting in the time and effort to get results, and honing in on your one key differentiator to help you break into a market.



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