Transitions between different content worlds and the importance of believing the story we tell ourselves

Shay, Managing Partner at Greenfield Partners, together with Yuda Doron, Avery Schwartz and Raz Mangel. Greenfield has over $500 million AUM and invests in early stage growth startups (Series B-C) to work with entrepreneurs on scaling the company.

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After long service as an Air Force pilot, Shay made a profound change in his life and went from pilot to entrepreneur arriving in the US with no experience in this field, and dealing with uncertainty and many challenges leaving his comfort zone. The mantra that accompanies him was & still is: 

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"You know yourself, no one knows your situation, act rationally." - There is no one who can really understand all the considerations in depth before making a decision and therefore you need to lay out all the considerations and act rationally within existing constraints. 

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In discussing decision making, I (Gali) emphasize the importance of the three brains - the mind, the heart and the gut. Shay emphasizes the significance of taking small steps even in crises in relation to the word "act" from his quote, because even in the biggest crisis if you get up every morning and take one or two steps it will make all the difference. Shay recognized the possibility of making mistakes but emphasized navigating the situation for personal growth.

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Looking back on the dot-com bubble, Shay experienced both positive and negative aspects, and emphasized the fundraising challenges during the 2001 bubble burst. He discussed the role of aggressive investors in tough market conditions and shared key takeaways from the experience he gained. 

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Shay's transition from entrepreneur to investor was a profound change that required time and self-belief. He stressed the importance of humility, hunger, moving forward and self-awareness during such transitions. The important lesson Shay shared with us around transitioning from one content world to another, in addition to understanding it's a process that takes time, is the importance of believing your own story. He shares that until he believed his own story when he went from being an entrepreneur to investor, the environment didn't believe him either. 

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We touched on many of the pressures experienced by entrepreneurs and the role of investors in helping companies move forward. We emphasized the importance of communication and transparency, while highlighting the importance of sharing the emotions we experience to help us cope with challenges and create transparent dialogue together with partners.