Entrepreneur // @Shopify President // @BigShotPodcast Creator

Joined June 2008
1,491 Photos and videos
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Shabbat Shalom. This week, I had the honour of giving the convocation speech at McGill. It is about my grandfather. It is about immigration. It is about entrepreneurship. It is about the courage to start before you feel ready. One of the greatest honours of my life. Full speech here.
Replying to @mcgillu
Here's my convocation speech (hint: it's about my immigrant family & entrepreneurship)
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Harley Finkelstein retweeted
Hearing these names read back to back gave me chills: Barry Diller. Jeffrey Katzenberg. Lloyd Blankfein. Michael Ovitz. Stephen Ross. Bobby Kotick. Irwin Winkler. When David and I started @BigShotPodcast it was a passion project. Today it's a small but mighty archive of Jewish entrepreneurship, chutzpah, grit, and stories that would otherwise be lost. I couldn't be prouder. Shabbat Shalom, friends 🙏
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For one glorious day, Canadians from every province, political party, and postal code came together in agreement: “That Globe and Mail headline was insane.” Nation-building works in mysterious ways.
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Harley Finkelstein retweeted
Let’s go
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Beautiful scene. More of this spirit and pride pls 🇨🇦
The scene in Toronto for the World Cup 🤯 (via @Devin_Heroux)
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You don’t have to love Elon Musk to recognize what this headline says about us. A country that spends more time criticizing wealth creation than encouraging it sends a clear message to builders: your success is tolerated, not celebrated. Canada should be the best place in the world to build ambitious companies. Headlines like this make us look like we’re not quite ready for that.
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Update:
Jun 12
JUST IN: SpaceX is now worth more than Canada
Community note
SpaceX's market cap is about $2 trillion. Canada's GDP is about $2.5 trillion per year. The post compares the company's valuation to the country's annual economic output. finance.yahoo.com/quote/SPAX.PVT/ worldometers.info/gdp/canada-gdp/
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This isn’t much better 🇬🇧
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Rocky is one of the greatest movies ever made. And it exists because two people had the audacity to bet on themselves before anyone else would. Stallone was an unknown actor who wrote the script for free and refused to sell it because he believed he was the one who should star in it. Irwin Winkler was the producer who trusted his own instincts when every studio said no. Because his instincts told him this movie needed to exist. I've been talking a lot about audacity lately. This is what it looks like. Two people who refuse to wait for permission. New @bigshotpodcast episode out now.
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Could not agree more with @saranormous. Commerce is not a prompt. Generic AI can write copy, generate images, or give plausible advice. But helping a merchant make the right call requires understanding the business down to the studs. Inventory. Margins. Pricing. Customers. Payments. Fulfillment. Fraud. Returns. Taxes. Apps. Goals. These are not thin wrappers. These are existential questions. That’s Sidekick inside Shopify: 20 years of commerce insight, context, and trust. Generic AI can sound right. Shopify can help merchants actually get it right.
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Rocky. Goodfellas. Raging Bull. Wolf of Wall Street. The Irishman. Creed. Irwin Winkler’s name may not be top billing on the poster. But his fingerprints are all over modern Hollywood. On the new @bigshotpodcast, we sat down with the invisible architect behind visible culture. This one is a masterclass in how chutzpah, relentless adaptability and a little bit of luck built Hollywood as we know it.
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Every object in your life is about to get an AI strategy. Apparently desks are first.
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The word "disruptor" gets thrown around a lot. @elfcosmetics actually earned it. First beauty brand on TikTok. First on Roblox. First ever TV commercial? The Super Bowl. They don't follow. They go first. A true disrupter. 5 brands. All on @Shopify. Welcome, e.l.f.
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Harley Finkelstein retweeted
Everyone's talking about AI-generated HTML. But have you tried giving your sites a zero-config API for saving data, file storage, AI, websockets, etc? We did this at Shopify. Runs on a single VM that costs $200/month, and it's changed the way we work. We call it Quick 👇🧵
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I tell stories about entrepreneurs. @Nikbentel tells stories through objects he creates. When we asked Nik to design something with us, he looked at an item that touches nearly every entrepreneur's product but almost no one thinks twice about: the yellow shipping strap. Then he turned it into a handbag.
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Le Mans: where normal people see a race and @tobi sees product market fit đź’Ş
24h of Le Mans this weekend
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It’s a beautiful day to give your haters something new to complain about while you keep building.
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