Iron Pillar


The Big Picture – In conversation with Iron Pillar Network Member – Jay Chakrapani

In the latest episode of Iron Pillar’s Big Picture podcast, I had a delightful conversation with Jay Chakrapani, my dear friend, MIT fraternity mate, former CTO of McGraw Hill,, Inc. and an early employee of Trilogy Education (acquired by 2U) and now CTO at GLG. Jay is a key member of the Iron Pillar Network and his expertise is extremely helpful as we evaluate and invest in companies like Skill-Lync disrupting the future of work and education.

I tapped into Jay’s remarkable career and especially his insights into the future or work and future of education, domains that are deeply important to him and to the Iron Pillar team. I loved his quote “I have always been drawn to situations where I could apply technology that could make a large and positive impact to a particular industry or market”

His core messages for entrepreneurs especially in the Ed-tech space were spot-on. Jay hit on several topics including:

  • Adaptive learning
  • Never burning bridges
  • Differences between bringing about innovation at large companies versus starting something new – Key question to ask: Is there a “discontinuous growth opportunity” within a given structure
  • It’s all about “execution”…ideas are cheap
  • Distill your ideas into super small wins that you can deliver within a predictable period of time
  • I am not a “zero to one” guy. I like professionalizing the operation post product-market fit
  • Why join IPN – besides the relationship that goes back decade, it’s about the fact that Iron Pillar thinks globally and back the thinking that ideas, innovation and businesses are not just for Silicon Valley
  • Technology is the big equalizer and bridges the opportunity gap
  • Covid has accelerated technology adoption in the way we work and the way we learn. There is going to be a “great equalization” of innovation and Iron Pillar is a new genre of VC that is at the heart of that transition

I hope you enjoy this incredible conversation with Jay. Thank you Jay for your endorsement, your generosity and helping the Iron Pillar portfolio companies, especially those disrupting the Future of Work or Future of Education.

About Mohanjit Jolly

Mohanjit Jolly

Partner at Iron Pillar bringing to the table more than 2 decades of investing and operation experience.