The discussion contrasts the roles of insiders and outsiders in venture capital, emphasizing how these identities shape opportunities. Insights on personal journeys reveal biases and the importance of authentic connections. The conversation also explores the dynamics of empire building, highlighting the insider's maintenance focus versus the outsider's quest for growth. Listeners gain perspectives on navigating the entrepreneurial landscape, learning that perseverance and collaboration are vital for success.
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question_answer ANECDOTE
Insider vs. Outsider Advice
Elizabeth Warren was advised to be an insider for influence.
Outsiders aren't listened to, while insiders have access but can't criticize each other.
insights INSIGHT
Defining Insiders and Outsiders
Insiders generally conform to established norms and are “in the know”.
Outsiders challenge conventions, offer unique perspectives, and may lack collective affirmation.
question_answer ANECDOTE
NFL Scout's Bias
Grant Gregory’s friend, a skilled football player, was told scouts favored established recruits.
Scouts prioritize their job security over betting on outsiders, even if they have potential.
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In this memoir, Elizabeth Warren recounts her journey from a modest childhood in Oklahoma to becoming a distinguished law professor and eventually a U.S. Senator. The book highlights her experiences with financial hardship, her education, and her career in law and politics. Warren discusses her battles against big banks and corporate lobbyists, her role in advising Congress on bankruptcy laws, and her advocacy for consumer protection. The book also touches on her personal life, including her family and her decision to run for public office at the age of 62.
Boyd
The Fighter Pilot Who Changed the Art of War
Robert Coram
This book tells the story of John Boyd, a fighter pilot who had a profound impact on military strategy and aviation. Boyd is credited with saving fighter aviation from the Strategic Air Command, developing the 'Energy–maneuverability theory' that influenced the design of fighter planes like the F-16, and creating the 'Aerial Attack Study,' which became the standard tactics manual for air forces worldwide. He also developed the OODA (Observe-Orient-Decide-Act) loop, a strategic concept that has been applied in various fields beyond military aviation. The book details Boyd's abrasive yet principled personality, his challenges against Pentagon bureaucracy, and his lasting legacy in military and business strategy[1][3][4].
Larry’s tone was in the friendly advice-category. He teed it up this way: I had a choice. I could be an insider or I could be an outsider. Outsiders can say whatever they want. But people on the inside don’t listen to them. Insiders, however, get lots of access and a chance to push their ideas. People — powerful people — listen to what they have to say. But insiders also understand one unbreakable rule: They don’t criticize other insiders. — Elizabeth Warren, A Fighting Chance
Grant and Hammad discuss the concept of Insiders and Outsiders and how this applies to founders and investors alike. Grant pulls the curtain back on how these relate to hiring, fundraising, and more. Hammad talks about his first impression of Grant in the Susa Fellowship program and Grant shares his path into venture. Hammad closes us out with sage advice: Play the hand of cards you’re dealt (and enjoy it while you do!)
Exploring what makes great companies and technologies work. Brought to you by Grant Gregory & Hammad Aslam. Grant is an investor at Cantos where he focuses on physical world technologies. Hammad is a Partner at Kivu Ventures, Susa’s growth fund. Learn more about the hosts:
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