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



In this candid conversation on "20vc" with host Harry Stebbings, Harley Finkelstein, president of Shopify, reflects on his journey from DJing at bar mitzvahs to spearheading Shopify's growth, emphasizing life lessons over business strategies. Harley discusses his personal evolution, the importance of being a present and empathetic partner and father, and the value of therapy in achieving these goals. He also shares his insights on leadership, the art of storytelling, and his mission to make entrepreneurship more accessible. Harley's partnership with Shopify co-founder Toby Lütke thrives on mutual respect, fun, and the ability to embrace each other's strengths, a dynamic that extends to his marriage and parenting approach. As he looks to the future, Harley is optimistic about fostering entrepreneurship and personal growth, both at Shopify and in his own life.

Summary Notes

Introduction to Harley Finkelstein's Background

  • Harley Finkelstein is the president of Shopify and has been instrumental in growing the company's revenue and team size.
  • Besides his role at Shopify, Harley is an advisor and has held board seats at various organizations.
  • He is also featured on CBC's Next Gen Dragons Den.

"Over the last twelve years, Harley's partnered with Toby to the tune of building Shopify's revenue to over $4.6 billion in 2021 and the team to over 10,000 employees."

The quote highlights Harley's significant contribution to the growth and success of Shopify, both in terms of revenue and team expansion.

Harvard Management Company (HMC) and Mercury

  • HMC manages Harvard University's endowment and invests in venture capital.
  • Mercury offers banking services tailored for startups, including banking accounts, debit cards, and integrations with other startup tools.

"Harvard Management Company is constantly seeking out the next generation of great investors and entrepreneurs."

This quote emphasizes HMC's commitment to investing in and supporting new investors and entrepreneurs.

Sprig User Research Platform

  • Sprig provides a platform for user research through in-product micro surveys and concept tests.
  • It is used by companies like Dropbox and Square to gather customer insights quickly.

"With Sprig, both teams can get their own way."

The quote suggests that Sprig's platform satisfies the needs of both user researchers and product teams by facilitating quick and efficient feedback collection.

Harley Finkelstein's Entrepreneurial Journey

  • Harley started his entrepreneurial journey as a teenager by starting a DJ company.
  • He later sold T-shirts to universities and moved his business online using Shopify.
  • Harley pursued law school to become a better entrepreneur, not to practice law.
  • He joined Shopify full-time after realizing his passion for entrepreneurship outweighed his interest in law.

"I became one of the first merchants to use Shopify, and I built an online t-shirt shop."

Harley's quote describes his early adoption of Shopify for his online T-shirt business, which was a stepping stone in his entrepreneurial path.

Dealing with Personal and Professional Setbacks

  • Harley uses entrepreneurship as a tool to overcome setbacks, such as his family's financial struggles.
  • He admires resilient individuals who find opportunities in devastating situations.
  • The COVID-19 pandemic forced businesses to adapt quickly, demonstrating the power of resilience and entrepreneurship.

"I think entrepreneurship, this incredible tool to dealing with incredible setback."

The quote encapsulates Harley's belief in entrepreneurship as a means to navigate and overcome life's challenges.

Empathy and Effective Communication

  • Harley learned the importance of effective communication and taking the time to ensure his team understood his vision.
  • He adopted new techniques, such as recording meetings and encouraging questions, to improve clarity and productivity.
  • As Shopify grew, Harley adapted his leadership and communication style to better suit the expanding team.

"I needed to change the way that I communicated. I needed to change the way that I provided a vision or direction."

This quote reflects Harley's realization that his approach to leadership and communication needed to evolve along with the growth of Shopify.## Empathy in Communication

  • Recognizing the importance of how the message is received, not just how it is delivered.
  • Empathy involves understanding the other person's perspective.
  • Empathy can enhance clarity in communication and improve outcomes.

"And I think that is all about empathy, which is like, okay, you think you're being clear. What does the other person think? If they don't think you're clear, then it doesn't matter what you think."

This quote emphasizes that effective communication is not just about the speaker's intention but also about the listener's understanding. Empathy is crucial in ensuring that the message is received as intended.

Vulnerability in Leadership

  • Discusses the challenge of being vulnerable as a leader without demotivating the team.
  • Vulnerability can be seen as a strength and can bring teams closer.
  • Sharing personal challenges, like anxiety, can make a leader more approachable and relatable.

"Can you be vulnerable today? And if so, how can you? And I guess you're kind of advising me here because I don't want to lose the morale. I don't want to lose the excitement."

Harry Stebbings asks Harley Finkelstein about the balance between vulnerability and maintaining team morale, indicating the complexity of leadership communication.

Harley's Personal Journey with Anxiety

  • Harley shares his experience with anxiety and the value of having a language to describe it.
  • Speaking about anxiety publicly led to support and advice from others.
  • Being open about personal challenges can make leaders seem more human and approachable.

"So one, I now was able to manage my anxiety better because now I have a term for it. There's nomenclature."

Harley Finkelstein explains how identifying his anxiety allowed him to seek information and support, demonstrating the power of self-awareness and communication.

Insecurities and Growth

  • Discusses the insecurities of not keeping up with the rapid growth of Shopify.
  • The importance of learning at a pace that matches or exceeds the rate of change.
  • Insecurity can be a driving force for personal and professional development.

"The most important law of ecology is this. For an organism to survive, the rate of learning must be equal to or greater than the rate of change happening around them."

Harley quotes a law of ecology to illustrate his insecurity about keeping up with Shopify's growth and the necessity for continuous learning.

Distinction Between Eustress and Distress

  • Eustress is motivating and action-oriented, while distress can be paralyzing.
  • Understanding the type of stress one is experiencing can lead to better management and harnessing of stress.

"First, so my wife's a psychotherapist, so I get all these sort of psychotherapist terms thrown at me on a daily basis. But one is just, it's simply two different reactions to stress, and one is paralyzing and debilitating, and the other one is action oriented and actually fairly motivating."

Harley explains the difference between eustress and distress, highlighting the impact of stress on performance and motivation.

Entrepreneurship as Personal Growth

  • Entrepreneurship is seen as a journey of personal growth.
  • Recognizing one's strengths and weaknesses is key to personal development.
  • Building a support system of people with complementary skills is essential.

"I heard this thing that entrepreneurship is a personal growth journey disguised as a business."

Harley reflects on how his journey with Shopify has been a vehicle for personal growth, showing the interconnectedness of personal development and entrepreneurial success.

The Art of Storytelling

  • Concerns about the decline of storytelling skills among founders.
  • The importance of a clear mission and its articulation through storytelling.
  • Storytelling is crucial for recruitment, employee engagement, and conveying the company's mission.

"I think we've lost the art of storytelling. I think a lot of founders today, 99% cannot tell a brilliant narrative, cannot really entice people along their journey."

Harry Stebbings expresses concern that many founders lack the ability to effectively tell their company's story, suggesting that storytelling is a critical skill for leaders.

Mission-Driven Companies

  • Successful companies often have a clear and compelling mission.
  • The mission is communicated to the world through storytelling.
  • A strong mission helps in recruiting and retaining employees who resonate with the company's values.

"I think what you're talking about is, actually, I would replace the term story with mission."

Harley argues that a company's mission is fundamental to its success and that storytelling is a means to communicate that mission to others.

Personal Connection to Work

  • Harley shares his personal connection to Shopify's mission.
  • The alignment between personal and professional life can be fulfilling.
  • Having a clear focus on one's strengths contributes to the impact one can make in their work.

"I'm lucky that the ven diagram of my personal life and my professional life overlaps so meaningfully."

Harley discusses the personal significance of Shopify's mission in his life, indicating the importance of aligning personal values with professional endeavors.## The Craft of Storytelling

  • Storytelling is essential for effective communication, especially in media like podcasts.
  • Harry Stebbings uses personal anecdotes to make his podcast relatable.
  • Harley Finkelstein emphasizes the importance of storytelling in business, particularly in his role at Shopify.
  • He shares the story of Gymshark's founder to illustrate the power of narrative in understanding a brand.

"You're talking about the craft of storytelling, and I think the craft of storytelling is incredibly important."

This quote highlights the significance of storytelling as a fundamental skill in various forms of communication, including podcasting and business leadership.

Building Successful Teams

  • Teams should consist of members with complementary, not overlapping, skill sets.
  • Diversity in skills and perspectives can lead to the creation of more robust and successful companies.
  • Harley Finkelstein describes his relationship with Toby as an example, where Toby focuses on product development and Harley on storytelling and brand awareness.

"If you look at some of the best teams out there that have built incredible companies, they are really different."

The quote stresses the value of assembling a team where each member brings unique skills and strengths, which collectively enhance the team's overall capabilities.

Conflict Resolution and Trust

  • Harley Finkelstein discusses the concept of "disagree, but commit" in professional relationships.
  • Trust is foundational for healthy debate and conflict resolution.
  • Shopify uses a "trust battery" metaphor to encourage constructive disagreement without personal conflict.
  • Mutual respect and having fun are considered key elements of a successful partnership.

"The key is to get your trust battery as high as possible. Because at that point, that's when debate, that's when disagreement becomes far richer."

This quote explains the "trust battery" concept, which is about building trust to a level where disagreements can be about ideas and not taken personally, thus enriching the discussion.

Maintaining a Successful Marriage

  • Harley Finkelstein acknowledges that social media often portrays only the positive aspects of relationships.
  • He emphasizes the importance of learning from others to improve as a spouse.
  • Harley and his wife Lindsay see themselves as a team, supporting each other in different roles.
  • They have been proactive in maintaining their relationship through couples therapy.

"We are a team. And sometimes I'm on team Lindsay because she's going through something. And sometimes she's on team Harley because I need something."

This quote encapsulates the teamwork approach to Harley's marriage, where both partners support each other through various challenges, reinforcing their bond.

Couples Counseling and Communication

  • Harley Finkelstein and his wife have been attending couples therapy since the early days of their marriage.
  • Therapy serves as a space to communicate openly and work on relationship dynamics.
  • Harley shares a communication tactic he learned: asking his wife if she wants him to listen or to help solve a problem, which has greatly improved their relationship.

"Do you want me just to listen or do you want me to help you solve it?"

This quote reflects a practical communication strategy that Harley uses to better support his wife, showcasing the benefits of clear communication in a relationship.

Balancing Entrepreneurship and Personal Life

  • Harley Finkelstein discusses the challenge of balancing the demands of entrepreneurship with personal relationships.
  • He emphasizes the importance of deciding whether to run a marriage like a business, recognizing that some principles may apply to both.
  • Harley and Lindsay have a ritual of date nights to maintain their connection, demonstrating the importance of dedicated personal time.

"How you do anything is how you do everything."

This quote suggests that the approach one takes in small tasks can reflect their overall attitude and behavior, which is relevant in both business and personal life.

Fatherhood and Presence

  • Harley admits he has not always been a great father, initially focusing on material aspects of care rather than being emotionally present.
  • He learns that presence and mindfulness are what his children value most.
  • Harley shares a realization from couples therapy about the importance of being truly present with his children.

"What actually my kids valued more was my presence. Was I actually there?"

This quote reveals Harley's insight into what truly matters to his children, emphasizing the importance of being emotionally and mindfully present as a parent.## Value of Attention in Parenting

  • Realizing the importance of being fully present for children.
  • The fear of being a superficially good parent rather than an authentically present one.
  • Making changes to ensure quality time with children.

The kids don't value some special pancake mix or some special bacon. The kids value, do they have your entire attention?

This quote emphasizes that children appreciate undivided attention from their parents more than material things or special treats.

Changes to Personal Routine

  • Adjusting daily schedule to prioritize family time.
  • Hiring a trainer to establish a consistent workout schedule.
  • Importance of being present for children's bedtime.
  • Scheduling family activities on weekends to ensure full attention.

I just hired a trainer... every day at 530 would show up at the house.

The speaker made a change to his daily routine by hiring a trainer to ensure he finishes work on time to spend the evening with his children.

Time Management and Scheduling

  • Using scheduling to balance work, fitness, and family time.
  • Importance of booking time for family activities.
  • The challenge of maintaining romance while being organized.

I will put in my calendar, like a two hour block to ski with Bailey.

This quote illustrates the speaker's method of ensuring dedicated time for family activities by scheduling them in advance.

Perspectives on Reading and Podcasts

  • The value of consuming content outside one's professional field.
  • The benefit of learning from different subjects and experts.

I find listening or reading about things that are completely outside my day to day is so incredibly interesting.

The speaker finds it enriching to engage with topics unrelated to his professional life, suggesting it can offer new insights and perspectives.

Reflection on Leadership

  • Admiration for leaders who bring others along on their journey.
  • The importance of compelling communication in leadership.
  • Learning from board members about organizational resilience and information processing.

There's a guy named John Hope Bryant that I recently met... He's amazing.

The speaker admires John Hope Bryant for his leadership and ability to inspire and mobilize people towards a common goal.

Traits for Children to Adopt

  • Desire for children to be passionate, kind, and ambitious.
  • The importance of being ambitious about the right things.

I want them to be passionate about something... I want them to be kind... I want them to be ambitious.

The speaker hopes his children will adopt these traits, which he values as essential for a fulfilling life.

Professional and Personal Goals

  • Aiming to encourage more people to try entrepreneurship.
  • Personal growth and being a great husband and father.
  • Optimism about the future and the world's direction.

I want to change the way the people consider entrepreneurship.

The speaker's professional goal is to make entrepreneurship more accessible and to change perceptions about it, while also focusing on personal development and family life.

Appreciation for the Podcast Discussion

  • Enjoyment of unexpected, meaningful conversations.
  • The value of discussing topics like marriage and fatherhood.

This is totally not what I thought we were going to talk about, but hopefully this is interesting.

The speaker expresses that the conversation took an unexpected but valuable turn, highlighting the importance of discussing personal topics.

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