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Articles by Harley
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Our image of an entrepreneur desperately needs an update--here's how we change it
Our image of an entrepreneur desperately needs an update--here's how we change it
"Young people are just smarter," Mark Zuckerberg infamously said to 650 aspiring entrepreneurs at a Y Combinator…
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17 Comments -
Why I Let My Employees (Literally) 'Ask Me Anything'Oct 3, 2018
Why I Let My Employees (Literally) 'Ask Me Anything'
Originally published at Forbes.com on November 23, 2016.
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7 Comments -
From "Side Hustle" To "Life's Work" -- Evolving The Gig EconomySep 12, 2018
From "Side Hustle" To "Life's Work" -- Evolving The Gig Economy
Originally published at Forbes.com on May 8, 2018.
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3 Comments -
5 Trends That Will Change The Way Your Customers Shop In 2018Aug 22, 2018
5 Trends That Will Change The Way Your Customers Shop In 2018
Originally published at Forbes.com on January 10, 2018.
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9 Comments
Activity
149K followers
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Harley Finkelstein shared thisMAC Cosmetics didn't follow beauty culture. It built it, and it didn't stop there. It turned makeup into a tool for self-expression. It was radically inclusive before inclusivity was a strategy. Its artists have shaped fashion, music, and pop culture. Four decades later, MAC is still dominating. Still built for the pros. Still setting the standard everyone else follows. But here's what most people never see. The complexity behind a brand like this is staggering. Thousands of products. Every shade. Every variant. Across one of the biggest beauty operations on earth. We shoulder that complexity, so MAC can focus on what it does best. Making the products that define culture, on a faster storefront with the best-converting checkout on the planet. Shoutout to Teifi Digital, Domaine, and Pipe17 for making this happen behind the scenes. Welcome to Shopify.
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Harley Finkelstein shared thisEntrepreneurs are some of the hardest working people I know, and some of the least celebrated. They rarely get the spotlight. So when there's a day that actually acknowledges it, we're going to lean all the way in. That's why we dropped the Entrepreneur Collection for Shopify Supply, on World Entrepreneurs' Day. We didn't hire models. We brought in real founders, and put their businesses at the center of the story. Because entrepreneur isn't a job title. It's an identity. And that's exactly who this collection is for. Now you can wear it too. https://lnkd.in/exrAisBU
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Harley Finkelstein shared thisCultural moments make headlines. Now they also make entrepreneurs. Here’s what I mean. May 8, 2025 at 1:25pm. A new pope is announced. Minutes later, a Shopify merchant is selling "da pope" t-shirts. That's the speed of commerce today. And it's why entrepreneurs are my favourite people. The guy behind it had spent years making one-liner shirts for Cubs fans. No factory. No warehouse. Just an idea and enough speed to act before the moment cooled off. That kind of speed used to be reserved for people who already had capital, inventory, and a manufacturing deal lined up. Not anymore. One person with an idea and a free afternoon can do what used to take a company months. That's what I love about this. Worth a read: https://lnkd.in/g7V-yPh3Commerce now moves at the speed of culture. And anyone can move with it.Commerce now moves at the speed of culture. And anyone can move with it.
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Harley Finkelstein shared thisBuilder Sundays might be the most Shopify thing we do. We open our offices every Sunday, where founders and builders show up for focused deep work. Side projects, early-stage startups, experiments. Solo builders and small teams, heads down, making things. Building can be lonely. Builder Sundays is the fix. You're in a room full of people using the same tools and chasing the same kind of goal, happy to tell you what they know that you don't. And at the end of every session, we do demos. Anyone can stand up and show what they've been working on, answer questions, and get real feedback. People have met their co-founders here. Some have met their first customer. It started as a tiny thing in Toronto, then Montréal. Now Ottawa is open too. New spots are released every Wednesday at noon ET for the following Sunday. If you're building something, come spend a Sunday with us. Bring your project. Keep going. buildersundays.ca
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Harley Finkelstein shared thisIf you’re a founder or operator of any commerce company in 2026: do one thing now. Read the post I’ve linked below. This is what the billion dollar brands of the next decade are focused on now. AI search. AI is the new discovery channel. Both traffic and orders to Shopify stores from AI channels have tripled since last year. It’s small today, but it’s growing fast. And here’s the best part. AI search is not fighting traditional organic search. It’s complementing it. In fact, shoppers are using it to do very different jobs. And, I cannot stress this enough. If you are running a business in 2026. You. Need. To. Know. This. There’s a lot in the report, but my top takeaway was this: AI search is conversational. Shoppers don’t talk to their agent in keywords. So you shouldn’t either. As usual, Shopify merchants are ahead of the game. Our Catalog structures product data so every and any AI partner can access it directly: giving agents the ability to discover, understand, and recommend our merchants’ products. No one can do this better than us, because we have 20 years (and billions of data points) on how people shop. But whether or not you’re on Shopify, this report breaks down how to make your products “agent-ready”. And there might be nothing more important than this if you want to succeed in the next era of commerce. AI search is a goldmine. If you know how to use it. But whatever you do, don’t underestimate it. https://lnkd.in/gNvjyY3WAI and organic search are doing different jobs: What Shopify's data shows (2026) - ShopifyAI and organic search are doing different jobs: What Shopify's data shows (2026) - Shopify
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Harley Finkelstein shared thisCommerce keeps getting more complex. That's exactly what makes Shopify more essential. One unified stack. World-class checkout. The whole journey, end to end. We are the commerce infrastructure for the future. Thank you Jim Cramer.
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Harley Finkelstein shared thisA harness for a French Bulldog. A car seat that sits three across in a sedan. A screenless phone for kids. These are all real products on Shopify already benefitting from AI search. AI is rewriting how people shop. Shopify merchants are as always, ahead of the curve. Thank you Fox Business Network for having me. It’s always great being on your show.
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Harley Finkelstein shared thisThe Q2 numbers are in, and it was a monster quarter. → $116B in merchant sales, up 32% YoY, our fifth straight quarter of 30%+ GMV growth → $3.6B revenue, up 34% YoY → $654M free cash flow, an 18% margin → Traffic and orders from AI channels both tripled YoY as ChatGPT, Google, and others become real discovery engines → 75% of AI-attributed orders came from outside the top 100 categories, the specialized long tail winning on relevance, not budget → Sidekick usage is up 3.6x YoY, helping merchants get to their first sale faster and run smarter after → Shop Pay crossed $400B in lifetime GMV → Iconic names across fashion, beauty, and retail all moved onto the platform this quarter Behind every one of these numbers is a simple job we've done for twenty years: absorb the complexity of commerce so merchants can focus on what they actually care about, their products and their customers. Today an entrepreneur can have an idea in the morning and their first sale by the end of the day. That's an entirely different velocity of entrepreneurship, and it's only accelerating. Watch the video for the full story on Q2 and what this new era means for entrepreneurs.
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Harley Finkelstein shared thisThe Economist just called America "an entrepreneur's paradise." From where I sit, that's not hype. It's the clearest shift I've seen in twenty years of building for entrepreneurs. Their explanation is AI. They're right that it matters. But AI isn't the whole story. It's the accelerant. For a century, ambition had a cost most people couldn't pay. Capital. A storefront. A team. Permission from someone who'd already made it. So people chose the path that promised stability, and the dream of being your own boss stayed a dream. It’s not that people got more ambitious. It's that the price of acting on that ambition is collapsing. But here's the part I find even more interesting. It's not just that more people are starting businesses. It's which ones are starting to win. For years, the internet rewarded the popular. The biggest, broadest brands won the top of the page, and anything specific got buried. That's changing. I've been saying this all year: discovery is shifting from popularity to relevance. From how many people know a brand to how well a product actually fits what someone wants. And when merit wins, the advantage quietly moves to the small, specialized business built for a particular customer. At Shopify, I get a front-row seat to this every day. The momentum isn't coming from the giants. It's coming from the specific, the specialized, the ones too small to have ever made sense in the old economy. AI didn't replace the entrepreneur. It created millions more. https://lnkd.in/gnyqWsPD
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Harley Finkelstein liked thisM·A·C Cosmetics is now live on Shopify in the U.S., an exciting moment in The Estee Lauder Companies' ongoing collaboration with Shopify. Bringing a brand as iconic and complex as M·A·C onto a unified commerce platform is no small undertaking and I’m proud of our teams for bringing this to fruition so quickly. Together with Shopify, we’re delivering seamless shopping experiences – helping consumers discover new products, explore the full brand, and shop M·A·C wherever and however they choose. This is the foundation for the future of shopping, through the emerging world of conversational and agentic commerce. And it's all in service of our number one priority: creating incredible experiences for our consumers. This is just the beginning as we continue to migrate more brands to Shopify this year. Congratulations to the teams at The Estée Lauder Companies Inc., MAC Cosmetics, and Shopify. https://lnkd.in/g2x7jpxt
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Harley Finkelstein liked thisHarley Finkelstein liked thisMAC Cosmetics US is now live on Shopify. We’re excited to celebrate the launch of M.A.C.’s new ecommerce experience, built in partnership with the teams at M.A.C. Cosmetics, The Estée Lauder Companies Inc., Shopify, Teifi Digital, Pipe17 and Domaine. For a business of this scale, the work went far beyond building a new storefront. Our team created a single headed codebase and flexible design system designed to serve multiple brands, each with its own distinct identity and commerce requirements. The result is an enterprise Shopify environment built with scale in mind: creating a shared foundation that can support MAC Cosmetics today and more brands across the Estée Lauder Companies portfolio to come. A major milestone for an ambitious, highly collaborative project. Explore the new MAC Cosmetics US experience: https://lnkd.in/gXv8MrE
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Harley Finkelstein liked thisHarley Finkelstein liked thisMAC Cosmetics is now live on Shopify in the U.S. This is an exciting step forward in the partnership between The Estée Lauder Companies and Shopify. Together we are reimagining how customers discover and shop for beauty online.
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Harley Finkelstein liked thisHarley Finkelstein liked this6 years ago today, Shopify President Harley Finkelstein stopped by 1909. Randomly, Matthew Ferrer called me asking if he could film for a Discovery Channel reality show featuring his startup VERSATTIRE. He buried the lede. A dozen film crew later, and coworking turned into a studio. And of course, the fellow eCommerce legend BRĒZ founder Aaron Nosbisch was there. Was a good day, that day.
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Harley Finkelstein liked thisHarley Finkelstein liked thisThose who know me know I love numbers, so here’s one I’m especially proud of: 1,000,000 orders. This week, Arctic Cool received Shopify milestone award recognizing our one-millionth order, a milestone reached by fewer than 0.1% of Shopify brands. While Shopify is only one of our channels, this award gave us a chance to pause and appreciate what we’ve built over the past eight years. Thank you to our customers, team, partners and everyone who has supported us along the way, and especially to my partner in business and life, Jessica Hawes ! If you’ve been part of the Arctic Cool journey, let us know how you first discovered the brand. Cheers to the next million. 🥂 #shopify #shopifymilestone Harley Finkelstein
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Harley Finkelstein liked thisHarley Finkelstein liked thisShopify President Harley Finkelstein says small businesses are benefiting the most from agentic commerce. "The merchants that seem to be benefiting the most from agentic commerce are not the big-box stores. It is the long tail of these specialized independent businesses." "On agentic alone, AI-driven traffic to Shopify stores was up 3x, orders were up 3x, and conversion from our Shopify catalog was 2x more than general AI scraping." "The volume in agentic commerce is small relative to the $116B [in Q2 merchant sales], but the trend and growth is real."
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