Lessons from Harley Finkelstein, President of Shopify

On Entrepreneurship and Building a Business

On the Modern Age of Entrepreneurship: “This is the greatest time ever, in the history of the world, to build a brand new business.” [1]
On the Core Purpose of Entrepreneurship: "I've always felt that entrepreneurship is a profound way to build something of value, And when things are rough, like they are right now, it's a way to survive. Maybe even thrive." [2]
On the New Path to Market: "This idea of shifting the sequence of events from product first, audience second to being audience first, product second. That is some of the coolest thing ever that that's ever happened in entrepreneurship." [4]
On the Entrepreneur's Unique Advantage: "If you're a coffee brand, Maxwell House has more money than you, Starbucks has more money than you... The one thing that they don't have is they don't have you, the entrepreneur.” [5]
On Strategic Intentionality: "There was a period of time where you could make a bunch of mistakes... I think now, you have to be a little bit more precise. You have to be a little bit more thoughtful." [5]
On Side Hustles: "Not everyone should commercialize their hobby, some hobbies should remain hobbies. But I do think that there is a real pent-up demand today that didn't exist 10 years ago for people saying you know what, I really love like tea... I'm going to start Firebelly Tea." [6]
On Acquiring Unique Skills: His mentor advised him to go to law school "not to become a lawyer but to be a better entrepreneur... to sharpen your point you should do something that is non-obvious." [7]
On Finding a Co-founder: "Most people start companies with people just like them... I think that's a terrible idea... walk across the street go to a different faculty... and find someone there to start a company with." [7]

On Leadership and Company Culture

On Re-qualifying for Your Job: “If you want to lead at a company like Shopify, you simply have to re-qualify for your job every single year.” [9]
On Vulnerability: “We're all better off when we take off the strong, iron facade, and speak with more vulnerability around how we're feeling.” [9]
On Maintaining a Startup Culture: "Even though we're a much bigger company... we very much culturally act like a startup... [The culture] should feel as ambitious, as optimistic, as enterprising, as entrepreneurial, as a one-person T-shirt business." [9]
On Specialized Leadership: “We like the idea of having very spiky objects,” referring to leaders who have deep expertise in specific areas rather than being generalists. [9]
On Hiring: "Often what we end up doing is we end up hiring entrepreneurs. We look for founders." [4]
On Remote Work: “The hybrid model often comes off as indecision... We're trying to be more decisive to say, 'work from anywhere, but make sure you and your team are getting together.'” [9]
On Being a Platform: "You know you're a platform when you create more value for others than you capture for yourself." [3]
On Empowering Employees: At Shopify, every new hire can drive positive impact within the organization, rather than just acclimatizing to a locked-in culture. [9]
On Impact Over Titles: He stepped down as COO to become President, moving from "managing many things adequately to doing one thing exceptionally." [10]
On Shopify's Core Mission: "We want to arm the rebels, we want to make sure entrepreneurs have everything they need to succeed—this was our objective from the start." [2]

On Personal Growth and Mindset

His Family Motto: "How you do anything is how you do everything." [11]
On Resilience: "Most people believe resiliency is this thing you either have or you don't have. And actually, it's not the case. Resiliency is learned." [5]
On Facing Hardship: "Every time it gets hard, you build new resilience and you are going to win, ultimately." [5]
On True Confidence: "True confidence isn't actually knowing what to do, it's knowing that whatever comes your way you will be able to figure it out." [12]
On Anxiety: He views anxiety as a potential "superpower when properly channeled." [1]
On Focus and Excellence: "What do you want to be world class at?" [11]
On Prioritization: "I think if you try to do all of it all the time you end up being very mediocre." [11]
On Reframing Failure: "We didn't view that as a massive failure we viewed that as a the successful discovery of something that did not work." [13]
On Incremental Progress: His experience climbing the equivalent of Mount Everest taught him the power of incremental progress. [1]
On Proactivity: “High agency is someone who sees a problem and says, 'I'm going to fix it' and then fixes it themselves.” [10]
On Personal Growth: “I need to grow equal or greater to the speed of how fast Shopify is growing.” [9]
On Finding Your Life's Work: "Does your personal mission and your professional mission do they overlap? Does the ven diagram overlap?" [13]
On Being Multi-dimensional: "I think more people are becoming more multi-dimensional, and actually that is a very good thing." [6]

On Strategy, Competition, and The Market

On Surviving Competition: "For a species to survive, they have to grow at a rate that is equal to or faster than the environment around them." [3]
On Passion as a Differentiator: "(The best) entrepreneurs just simply out-care other people. You can't beat someone who cares more than you." [10]
On Multi-Channel Presence: “If you're overly caught up in one particular channel and that channel disintegrates or goes out of fashion, you're going to scramble.” [14]
On Personal Branding: "Nobody wants to follow a corporate brand anymore... they want to follow you, they want to follow the person behind the company behind the product." [13]
On Authenticity in Branding: "This idea of having like this work life separation, I think is is is completely dated... there's no separation between your work persona and your personal persona." [13]
On the Power of Enthusiasm: "Part of... our success has been we simply just have more enthusiasm and more care about the product and the business than others do." [13]
On Being Resilient, Not Fragile: "We are not fragile. We are resilient." [2]
On the Value of His Own Store: Running his own Shopify store, Firebelly Tea, has been "one of the greatest tools... that has made me a better leader at Shopify." [7]
On Finding a Good Partner: “Most people need someone else to help them pull up to the next level.” [10]
On Managing Relationships: He categorizes people as "energy vampires" or "energy catalysts" and chooses to spend his time only with the catalysts. [10]
On Storytelling as a Benchmark: Every person at Shopify should be able to "give the keynote about how they're doing their job completely different than everybody in the crowd." [11]
On Analyzing Mistakes: "You have to rub your nose in your mistakes. Most people hide their mistakes. Harley analyzes his. Guess who improves faster." [10]
On the Scarcity Mindset: "I still don't think I'm doing enough, that I have enough, that I am enough," which he attributes to his family's history and which fuels his drive. [11]

Learn more:

Lessons from Harley Finkelstein, President of Shopify

On Entrepreneurship and Building a Business

On Leadership and Company Culture

On Personal Growth and Mindset

On Strategy, Competition, and The Market

Written by Antoine Buteau

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