From High School Dropout to CEO
Episode 3
November 21, 2018

From High School Dropout to CEO

With Sahil Jain, Co-Founder and CEO of AdStage

In this episode, Sahil shares his journey from dropping out of high school to work for Yahoo! at age 17, to building his own company and the many invaluable lessons and insights he learned along the way.

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In this Episode You'll Hear About:

  • How and why Sahil dropped out of high school
  • How he landed a job at Yahoo! full-time at age 17
  • His experience working for AOL at age 19 and why he got fired
  • The valuable lessons he learned from his first startup
  • What prompted Sahil to launch AdStage
  • Why he’s not a big fan of outsourcing
  • How his emotions impact his business and how he stays consistent and patient.
  • His process for hiring the right people and how he gauges if the applicant is the right fit
  • Why his company hosts hackathons
  • His experience in raising capital for his business and tips on pitching
  • Why he thinks staying naive is an important part of success
  • His perspective on the future of digital media  & advertising
  • His advice for aspiring founders or anyone looking to start a business

To Find Out More:


  • "It's really important who you start a company with and it's really important to pick your founders properly and people who you get along with philosophically as well as just in general."
  • "My co-founder and I often remind ourselves that if we're having a really bad day, we can't bring it in with us to the office."
  • "Hiring is your most important job as a founder and as a leader."
  • "Getting someone excited (about your business) can be done in many many different ways."
  • When it comes to fundraising: "I think the most important thing is authenticity."

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