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20VC: Shopify President, Harley Finkelstein on What is Being a Good Husband, What is Being a Good Father & How to Embrace Vulnerability and Authenticity in Leadership and Marriage

Mar 7, 2022

Harley Finkelstein, President of Shopify and a prominent entrepreneur, shares insights from his journey in building a billion-dollar tech giant. He delves into the importance of vulnerability and authenticity in leadership, revealing personal growth and insecurities. Harley discusses the art of marriage, emphasizing communication and collaboration with his wife. He illustrates how fatherhood reshapes priorities and values, while advocating for balance between work and family life, ultimately inspiring listeners to embrace their own journeys.

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ANECDOTE

Early Entrepreneurial Ventures

Harley Finkelstein's entrepreneurial journey began at 13, DJing at Bar Mitzvahs.
Later, he sold t-shirts to support his family after they faced financial hardship.

INSIGHT

Resilience Through Entrepreneurship

People react to setbacks with either resistance or resilience.
Entrepreneurship offers a tool for resilience, turning setbacks into opportunities.

ADVICE

Effective Communication

Effective communication requires understanding how others receive information.
Check for understanding and iterate to ensure clarity, even if it takes more time.

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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?

Item’s Mentioned In Today’s Episode with Harley Finkelstein

Harley’s Favourite Book: The Book of Ichigo Ichie: The Art of Making the Most of Every Moment, the Japanese Way