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Shai Wininger
3,691 posts
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Shai Wininger
@shai_wininger
Tech entrepreneur🎗️🇮🇱🇺🇸. CoFounder and President @ Lemonade (NYSE:LMND), CoFounder of Fiverr (NYSE:FVRR). Mixer of Tech, Design and AI.
lemonade.com
Joined December 2007
186
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29.3K
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  • Pinned
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    Shai Wininger
    @shai_wininger
    Jan 21
    Thanks @elonmusk! This feels like the beginning of a wonderful friendship.
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    Elon Musk
    X
    @elonmusk
    Jan 21
    Insurance is half price when Tesla self-driving is activated, because it increases safety so much
    197K
  • user avatar
    Shai Wininger
    @shai_wininger
    Oct 17, 2025
    If @elonmusk is game, we'd be happy to explore insuring Tesla FSD miles for (almost) free.
    user avatar
    Shai Wininger
    @shai_wininger
    Oct 16, 2025
    We’re starting to roll out direct integration with @Tesla vehicles, removing the need for a UBI device in our Pay Per Mile product. This makes activating Lemonade Car on Teslas effortless and lets us cut hardware and shipping costs, helping lower prices for Tesla drivers even
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    1.9M
  • user avatar
    Shai Wininger
    @shai_wininger
    Oct 16, 2025
    We’re starting to roll out direct integration with @Tesla vehicles, removing the need for a UBI device in our Pay Per Mile product. This makes activating Lemonade Car on Teslas effortless and lets us cut hardware and shipping costs, helping lower prices for Tesla drivers even
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    00:00
    1.6M
  • user avatar
    Shai Wininger
    @shai_wininger
    Jul 28, 2022
    And… we’re closed! @Metromile is now a @Lemonade_Inc company! In return for $145m in $LMND stock, we got over $155m in cash + $110m in car premiums + 49 state licensed insurance entity + data from 500 million car trips!
  • user avatar
    Shai Wininger
    @shai_wininger
    Nov 5, 2025
    .@Lemonade_Inc's Q3 2025 results: Highlights (YoY): 🚀 8th consecutive quarter of accelerating growth 💵 $1.16 Billion top line (IFP +30%, ahead of plan) 🔥 Gross Profit $$ increased +113% to $80m 🔥 Gross Profit Margin at 41% 🔥 2.87 million Customers (+24%) 🔥 Adj. EBITDA loss
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    196K
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    Shai Wininger
    @shai_wininger
    Nov 5, 2025
    Alright. Back to work.
    58K
  • user avatar
    Shai Wininger
    @shai_wininger
    Aug 5, 2025
    Thrilled to share @Lemonade_Inc's results for Q2 2025 🚀 $1.083 Billion In-Force Premium, 7th Q of accelerating growth (+29% YoY) 🚀 Loss Ratio: 67% (12pt improvement YoY!) 🚀 Generated $25M of adj. Free Cash Flow 🚀 Gross Margin up 14pts to 39%, Gross Profit +109% 🚀 2.7M
    109K
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    Shai Wininger
    @shai_wininger
    Feb 3, 2023
    למה אני ולמונייד לוקחים חלק פעיל במאבק לשימור הדמוקרטיה הישראלית. מכתב פתוח לעובדי @Lemonade_Inc
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    Why Lemonade joined the fight for Israel’s democracy
    From lemonade.com
    48K
  • user avatar
    Shai Wininger
    @shai_wininger
    Oct 8, 2023
    Before you get a stream of fake news coming from various politically driven media sources, here's what happened yesterday in Israel: - Hundreds of heavily armed Islamist murderers breached the Gaza border into Israel. - They went into innocent civilian families homes with one
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    80K
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    Shai Wininger
    @shai_wininger
    Nov 7, 2025
    We’re so lucky to have such an incredible retail investor community! It feels like a new kind of partnership, maybe even friendship, between company leaders and the investors who truly get it. All within regulatory limits, of course 😉
    49K
  • user avatar
    Shai Wininger
    @shai_wininger
    Oct 17, 2023
    Important update: the explosion in the hospital in Gaza was caused by a failed terrorists rocket launch meant to hit Israel. This is critically important because Israel will be blamed for it.
    17K
  • user avatar
    Shai Wininger
    @shai_wininger
    May 28, 2025
    In under 48 hours, 100% of the @Lemonade_Inc engineering team had switched to agentic coding. We've been building our AI-powered Autonomous Organization for the last decade and have learned that incorporating AI has deep psychological, operational, and technical aspects that are
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    178K
  • user avatar
    Shai Wininger
    @shai_wininger
    Mar 4, 2023
    יותר מ 400,000 איש יצאו להפגין הערב נגד ההפיכה השלטונית. מדובר באחת ההפגנות הגדולות בתולדות המדינה! - העם צ ע ק את דברו, ואף אחד בממשלה לא מקשיב. הדיקטטורה כבר כאן.
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    20K
  • user avatar
    Shai Wininger
    @shai_wininger
    Nov 7, 2023
    2,000,000 @Lemonade_Inc customers 🚀
    22K

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