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
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
The Twenty Minute VC
4.4 • 637 Ratings
🗓️ 7 March 2022
⏱️ 49 minutes
🧾️ Download transcript
Summary
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
Transcript
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| 0:00.0 | We are back. This is 20VC with me, Harry Stebbing. Today's show is a special show. The first time I |
| 0:04.7 | had this guest on it was over five years ago. And this discussion, it's really a good sign of how |
| 0:08.9 | the show's changed over the years. This conversation is less about business, but more a discussion |
| 0:13.3 | on life, marriage, parenting. Fetso was probably pretty out of my depth. And so with that, |
| 0:18.0 | I'm thrilled to welcome my good friend Harley Finkelstein, president at Shopify, |
| 0:21.6 | the platform modern commerce is built on. Over the last 12 years, Harley's partner with Toby, |
| 0:26.7 | to the tune of building Shopify's revenue to over $4.6 billion in 2021, and the team to over 10,000 |
| 0:32.8 | employees. On the side, Harley's also an advisor to Felice's Ventures, and in the past has held board seats at CBC, OMA's Ventures and the C-100. |
| 0:41.0 | And if that wasn't enough, you can also check Harley out on a screen near you as one of the dragons on CBC's next-gen-Dragons Den. |
| 0:47.6 | But before we move into the episode today, Harvard Management Company is constantly seeking out the next generation of great investors and entrepreneurs. |
| 0:55.1 | HMC has managed Harvard University's endowment for nearly 50 years and was one of the first |
| 0:59.9 | institutional investors in venture capital. Their experience in long-term investment horizon |
| 1:04.6 | makes them ideal partners to get world-changing ideas on a path to viability and success. They work as a |
| 1:10.7 | true partner providing |
| 1:11.7 | insightful perspectives to help managers succeed. I personally have had the pleasure of working |
| 1:16.4 | with the HMC team and can say that they're truly exceptional partners, people and incredibly |
| 1:21.2 | savvy investors. Whether you are launching your first fund or your fifth, HMC welcomes the |
| 1:26.3 | opportunity to partner with both developing |
| 1:28.1 | and established managers. Have an idea you want to share with the team? Just send it to venture |
| 1:32.6 | at HMC.harvard.edu. And speaking of amazing partners with HMC there, Mercury is building |
| 1:39.7 | full stack banking for startups. Applying under 10 minutes from anywhere for FDIC insured bank accounts, |
| 1:45.7 | physical and virtual debit cards, domestic and international wires, and integrations with |
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