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Can I Laugh On Your Shoulder?

Jun 23, 2021

My guest today is Dilan Dane, CEO of System2, the first relationship based, technology accelerated fitness brand that prioritizes longevity over quick fix exercise fads. He grew up in Sri Lanka, and his family’s income was less than $20 a month.

Through the kindness and generosity of others, Dilan was able to move to the U.S. at 20 and received a scholarship and financial aid to attend MIT, where he studied computer science and physics. It was not always easy because he barely spoke English and struggled with social anxiety. He was completely overwhelmed and felt physically and mentally exhausted.

After passing out during a final exam, a professor offered Dilan the chance to take the exam again if he sought help immediately for his depression. Dilan eventually learned about fitness and therapy, which changed his life. That led him to found System2.

3:58 – Dilan 101

  • He lives in San Francisco and runs a fitness/tech startup company. He wants to bring a team of coaches to every human.
  • Growing up in Sri Lanka, his dad was a police officer and his mom was a housewife.
  • Dilan was always good in school and was encouraged to apply to U.S. universities.

11:48 – Dilan’s childhood

  • He had a very complicated relationship with his father. His father was a good man who wanted to provide for his family, but he struggled to do that and had problems with alcohol and anger issues.
  • He craved his father’s love the most and wanted his father to see him.
  • His father was so proud that Dilan was top of his class, and that became Dilan’s identity. He craved that recognition and love.

18:45 – An angelic professor

  • An angelic professor made a huge impact on Dilan’s life. He noticed that Dilan did well in class but failed finals and encouraged Dilan to meet with a therapist.
  • The therapist encouraged Dilan to exercise, and the habit stuck.

30:59 – Fitness world

  • What really helps with mental health is changing your core set of habits, including moving your body, Dilan says.

34:50 – System2

  • Besides fitness, Dilan is also passionate about artificial intelligence. Due to recent advancements, he thought there might be a way to take personal training and make it scalable.
  • It would give trainers multiple eyes, so they can see their clients when they work out in person, at home or on the road.

40:25 – How System2 works

  • People do better when they’re not struggling alone. System2 gives people a coach, trainer and friend who helps people move forward in their journey.
  • People pay $99 a month and get a custom program.

49:36 – Get to know you

  • Most unusual talent? Trusting people very quickly.
  • Something important he doesn't talk about a lot? Spending more time with his aging parents.
  • Who would play him in a movie? Jake Gyllenhaal


“Having the opportunity to learn from incredible people in their respective fields, that was very inspired.”

“There’s a running joke in Silicon Valley that all the startup founders have daddy issues.”

“MIT is a very intense and hard place to survive at. Not everyone survives that place, but I did.”

“I feel like a lot of us have, in some way, this angelic person show up in your life, and it might be for just like a moment, but that really makes a big difference in your life.”

“I sometimes think all problems are problems of loneliness.”


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