About Values, Startup Culture, and Pink Lemonades

Shai Wininger,
Co-founder, President, and COO of Lemonade

Shai is the co-founder, president and COO of Lemonade which recently went public on NYSE and is now valued in billions of dollars. He is also the founder of Fiverr, which went public the year before. 

In an honest and open conversation, Shai shed light on recurring questions and themes throughout his 30-year entrepreneurial journey: 

  • How he engaged in life and celebrated wins while taking two companies public within the span of a year
  • How to overcome our inherited negative beliefs like ‘being too modest’ and ‘not taking money from others,’ and how does it manage us when meeting investors? 
  • How to overcome our fears?
  • What is the best way to build strong & balanced relationships with investors? 

We had an in-depth conversation about values as a mechanism of decision-making. Shai freely shares the values that are the basis of Lemonade and its people, and how those are also the key to choosing the right investors & employees. For Shai, the answer is that everything starts within, at home. 

Shai shared his own truth about his currency of happiness, discussed the gorgeous fuchsia color of Lemonade, and the essence of our wish for pink lemonades in insurance and life itself. We concluded that the best book we'll ever read and learn from is our own and how we should follow our gut feelings. Last but not least, Shai reflects and shares that sometimes, the best thing to do is, quite simply, the hardest. 

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