Sahil Bloom is a writer who attempts to demystify the world. He’s an investor, advisor, and creator. As a pitcher at Stanford, he once gave up a grand slam on ESPN in 2012 and he’s still waiting for it to land. Sahil is an angel investor in 25+ startups across the technology landscape. In this capacity, he works directly with entrepreneurs and founders to identify and execute against core value creation initiatives to build scalable, sustainable value for all stakeholders.

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The Learning Leader Show

  • Writing makes you better at everything you do. Writing is the best way to expose gaps in your thinking. When you write, you think better.
  • The makeup of a great coach – Never too big to do the small things. They push you beyond what you think you’re capable of. Everyone should take a moment and say thank you to someone who has done this for them.
  • Learning Circles — Develop a circle of people to collectively learn with. Push your thinking. I do this with my Learning Leader Circles and it’s some of the most rewarding work I do.
  • Why the cheeky Twitter bio? (“Once gave up a home run on ESPN that hasn’t landed yet”). “People take themselves too seriously.”
  • The difference between big public failures and private ones: “I think private failures can shape you more.”
  • Freshman year at Stanford was a grind… “I thought I was hot shit.” “Are you willing to spring when the distance is unknown?”
    • It’s all about how you bounce back from failures.
    • “You need to be able to take constructive feedback. You can’t crumble.”
  • Sahil asks, “What do I want to instill in my child?” Let them fail… It’s the greatest experience.
  • Angel Investing – An individual who provides money to start-ups.
  • The “must-have” qualities in a person for Sahil to invest in them: Resilience and Grit. “You’re going to get knocked around. They are willing to die before they’ll fail.”
    • “I’m driven by relationships over data points. I like to ask: Tell me about a time you got your ass kicked…”
    • Sahil invests because he learns so much through the process of it. The intellectual returns make it worth it.
  • “Writing is the best way to expose gaps in your thinking. It makes you better at everything you do.”
  • Be a teacher: “I’m learning alongside you.”
  • Great storytelling… “It is a built skill.”
    • Disney, Pixar… It’s a foundational skill. They infuse personality in writing.
  • The three biggest keys to storytelling:
    • Elicit an emotional response
    • Novelty – That “Oh wow!” moment
    • Punchy & Concise – “I didn’t have time to write a short letter so I wrote a long one instead.”
  • Viral tweet threads – It started in May 2020 for Sahil. He went from a few followers to hundreds of thousands…
  • Be “Positive Sum.” The world is positive sum. A rising tide lifts all boats. You should genuinely root for others to succeed.
  • The makeup of a great coach:
    • In the trenches with the team – never too big to do the small things
    • Willing to challenge you and call you out. They help you get better
    • They push your thinking
  • Coach John Beverly (Sahil’s high school baseball coach)
    • He was first to suggest that Stanford could be a reality for Sahil (“He was nuts”)
    • He had very high expectations
    • He believed in Sahil more than Sahil believed in himself
    • He changed the trajectory of people
  • Cognitive bias – High expectations lead to higher performance
    • You need to vocalize your appreciation for those who have pushed your thinking and expected a lot from you
  • The power of learning circles:
    • There is push & pull with others
    • Helps you develop circles of friends to collectively learn with and push your thinking
  • Apply to be part of my Leadership Circle


More Learning:

Episode 078: Kat Cole – From Hooters Waitress To President of Cinnabon

Episode 216: Jim Collins — How To Go From Good To Great

Episode #300: AJ & Keith Hawk – How To Instill Work Ethic & Curiosity In Your Children

Episode #303General Stanley McChrystal – The New Definition Of Leadership