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Shopify President, Harley Finkelstein on What is Being a Good Husband | Full Interview

Harley Finkelstein is the President of Shopify, the platform modern commerce is built on. Over the last 12 years, Harley has partnered with Tobi to the tune of building Shopify’s revenue to over $4.6BN in 2021 and the team to over 10,000 employees. On the side, Harley is an Advisor to Felicis Ventures and in the past has held board seats at CBC, Omers Ventures and The C100. If that was not enough, you can see Harley on a screen near you as one of the “Dragons” on CBC’s Next Gen Den. In Today’s Episode with Harley Finkelstein You Will Learn: 1.) The Founding Story: -What was Harley’s first entrepreneurial endeavour? -How did seeing his family lose everything impact Harley’s mindset and ambition? -How did Harley first meet Tobi @ Shopify? How did the Shopify journey begin? 2.) Leadership Lessons: -How has Harley changed as a leader over the 13 years with Shopify? -How does Harley embrace vulnerability and authenticity in his communication with the team? -What is Harley most insecure about when he looks at leadership today? -What have been some of the biggest lessons Harley has learned from his board on what great leadership is? 3.) The Art of Marriage: -What does Harley believe makes the most successful marriage? -Why have Harley and his wife been seeing a marriage therapist from the -early days? -What is the biggest mistake people make when communicating with partners? -How has Harley changed as a husband over the years? 4.) The Joy of Fatherhood: -Does Harley always believe he has been a good father? -What was his realisation moment that he was not being the father he wanted to be? -What core elements of his behaviour did he change? How did that impact his relationship with his kids? -How does Harley ensure he performs at the highest level while also being there and being present for his family? #HarleyFinkelstein #Shopify #20VC #VentureCapital #HarryStebbings #fatherhood #newparents #business #productmanager

Harry StebbingshostHarley Finkelsteinguest
Mar 10, 202259mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Shopify President Harley Finkelstein On Love, Leadership, And Growth

  1. Harley Finkelstein traces his journey from scrappy teenage entrepreneur to President of Shopify, framing entrepreneurship as his primary tool for surviving and transforming hardship. He explains how personal setbacks, including his family losing everything and living with anxiety, shaped his mindset toward resilience, learning speed, and service to entrepreneurs globally.
  2. The conversation dives deeply into emotional leadership: empathy, listening, vulnerability, and the importance of storytelling and clear mission for building enduring companies and motivating teams. Harley shares concrete tactics for being a better communicator, partner, and father, such as recording meetings, explicitly inviting confusion, and seeking coaching and therapy.
  3. A large part of the interview explores his marriage and fatherhood—how couples counseling, rituals like date night, and explicit communication (“do you want me to listen or solve?”) help him build a strong foundation at home that enables high performance at work.
  4. He closes with his long‑term ambition for Shopify to become “the entrepreneurship company” and his personal goal to keep learning faster than the rate of change around him, while remaining optimistic about the future of entrepreneurship and society.

IDEAS WORTH REMEMBERING

5 ideas

Use entrepreneurship as a practical tool for survival and self‑actualization.

Harley repeatedly turned to entrepreneurship when his family lost everything or when his career felt misaligned, showing that business-building can be both a financial lifeline and a path to meaningful work.

Resilience beats resistance: channel stress into action (eustress) instead of paralysis (distress).

He contrasts those who tried to ‘wait out’ COVID with those who adapted, arguing that anxiety and pressure, when understood and discussed openly, can become a powerful motivator rather than a crippling force.

Great leadership requires slowing down communication to go faster overall.

Moving from rushed 10‑minute ‘bull in a china shop’ meetings to longer, recorded, clarifying sessions made his team more productive and aligned, proving that surface efficiency can actually destroy true efficiency.

Vulnerability and honesty make leaders more approachable and more effective.

By openly sharing his anxiety internally and externally, Harley received coping tools from others and discovered that authentic vulnerability deepens connection and increases the impact of his motivational messages.

Know your spikes and hire to fill your gaps, not mirror yourself.

He emphasizes being ‘spiky’—world‑class at a few things like storytelling and evangelism—while delegating operations and detail work to others, and building leadership teams whose strengths minimally overlap.

WORDS WORTH SAVING

5 quotes

Entrepreneurship is a personal growth journey disguised as a business.

— Harley Finkelstein

For an organism to survive, the rate of learning must be equal to or greater than the rate of change happening around them.

— Harley Finkelstein (quoting an ecology principle)

Vulnerability, when it’s true and not performative, can come off as an incredible strength, not a weakness.

— Harley Finkelstein

We don’t want to create river stones at Shopify. I don’t want to be a river stone. I want to be spiky in certain areas.

— Harley Finkelstein

You want to go fast, go alone. You want to go far, go together.

— Harley Finkelstein

Harley’s entrepreneurial origin story and path to becoming President of ShopifyResilience, anxiety, and using entrepreneurship to navigate setbacksEmpathetic leadership, communication, and vulnerability in high-growth companiesMission, storytelling, and the ‘lost art’ of narrative for foundersBuilding a strong partnership with a founder/CEO and managing disagreementWhat it means to be a good husband: teamwork, therapy, and ritualsRedefining fatherhood: presence over performance and practical lifestyle changes

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