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Shai Wininger

Co-Founder, Fiverr

Search every verified Shai Wininger interview, podcast appearance, and on-the-record quote β€” each transcript cross-checked by AI and human review to confirm speaker identity. Shai Wininger, co-founder of Fiverr and Lemonade, has discussed the insurance industry's conflict of interest, stating that "every dollar that I claim is a dollar less on their bottom line." He described Lemonade's model, where the company takes a flat 20% fee and donates remaining premiums to causes chosen by customers, as a way to eliminate that conflict. Wininger noted that about 30% of claims at Lemonade are processed by a bot in seconds. Wininger has also spoken about Fiverr's growth and operational challenges. He recalled an incident where PayPal's anti-fraud system shut down Fiverr's transactions at midnight, which he said "we actually thought would kill us." He advocated for a data-driven culture, saying that "one out of eight things that you're gonna build will actually make an impact" and that "data wins and discussions end" when testing ideas. Wininger described the $5 entry point as "the ability to try something before you actually pay a higher amount."

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