The Power of Contrarianism in Entrepreneurship

This chapter discusses the importance of contrarianism in entrepreneurship, focusing on the potential of creating new industries instead of merely altering existing products. It highlights the need for unique insights and the challenges entrepreneurs face in distinguishing between innovative contrarian views and misguided ideas.

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The latest episode of The Eric Ries Show features my conversation with Reid Hoffman. Executive Vice President of PayPal, co-founder of LinkedIn, and legendary investor at Greylock Partners are just a few of his official roles that have changed our world. He’s also been a mentor to countless founders of iconic companies like Airbnb, Facebook, and OpenAI. He’s an author, a podcast host – both Masters of Scale and his new show, Possible, with Aria Finger – and perhaps most importantly a crucial steward of AI, including co-founding Inflection AI, a Public Benefit Corporation, in 2022.

Reid has also long been a voice of moral clarity and a stabilizing influence on the tech ecosystem, supporting people who are working to make the world a better place at every level. He’s a firm believer that “the way that we express ourselves over time is by being citizens of the polis – tribal members.” That includes not just supporting the legal system and democratic process but also building organizations “from the founding and through scaling and ongoing iteration to have a functional and healthy society.”

We talked about all of this, as well as AI, from multiple angles – including the story of how he came to broker the first meeting between Sam Altman and Satya Nadella that led to the OpenAI-Microsoft partnership. He also had a lot to say about how AI will work as a meta-tool for all the other tools we use. We are, as he said,” homo techne,” – meaning we evolve through the technology we make.

We also broke down his famous saying that “entrepreneurship is like jumping off a cliff and assembling the plane on the way down” and:

• The human tendency to form groups

• The relationship between doing good for people and profits

• AI as a meta-tool

• What he looks for in a leader

• The necessity of evolving culture

• Being willing to take public positions

• His thoughts on the economy and the upcoming election

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