Why do people hesitate to pursue entrepreneurship, and how has this changed?

Many people perceive entrepreneurship as financially risky or lacking in know-how. Historically, capital was the main ingredient for starting a business. However, today, the cost of failure is near zero, and formal business education is less critical, making it more accessible for anyone to start.

How important is passion in entrepreneurship?

Passion can be a catalyst, but necessity/desperation is also a powerful driver. While pure passion for the product isn't always present at the start, it's crucial to genuinely like what you're doing for long-term success. Harley cites his T-shirt business, driven by survival, versus his passion for Shopify's mission.

Should entrepreneurs seek therapy?

Harley Finkelstein believes self-aware entrepreneurs should consider therapy as a 'hack' to address personal traits and mindsets more effectively. He compares finding the right therapist to finding the right partner, emphasizing that a bad experience with one doesn't invalidate the entire concept.

What is Shopify's philosophy on failure?

Shopify views failure as the 'discovery of something that didn't work,' a concept taught by founder Toby Lütke. This reframing encourages learning and improvement for future endeavors, allowing the company to boldly launch many new features and products.

How can developing 'spiky' skill sets lead to greater entrepreneurial success?

Spiky skill sets involve going deep on one core area while gaining complementary, often unobvious, skills from other domains. This creates unique value and reduces competition, as seen in Steve Jobs' typography knowledge or Harley's legal education making him a better entrepreneur.

How do hobbies contribute to effective leadership and innovation?

Engaging in hobbies, even small ones like starting a tea or ice cream business, can build empathy for customers and help leaders understand the functionality of their own products. These 'Sunday afternoon activities' foster innovation and provide valuable real-world experience that translates to better leadership.

How should new entrepreneurs approach starting a business without feeling overwhelmed?

New entrepreneurs should start small by focusing on a hobby they enjoy, removing the expectation of immediate massive success, and allowing themselves to 'stumble forward.' The low cost of failure today means testing ideas is accessible, with many successful Shopify merchants starting accidentally or without a formal business plan.

What is Harley's framework for effective prioritization?

Harley prioritizes by calendaring everything important, both professionally and personally. This turns 'nice-to-haves' into 'must-haves' and ensures dedication to key areas like family, work, and charity, guided by the 'ikigai' concept of finding purpose and value.

How does Shopify approach remote work and team collaboration?

Shopify operates under a 'digital by design' model, allowing employees to work from anywhere. While physical offices are 'bursting locations' for occasional team gatherings, the company mandates quarterly in-person team meetings to foster connection and trust, acknowledging no perfect solution exists.

Why is vulnerability important, especially for men, and what is its effect?

Vulnerability, when shared with true friends and family, is a magnet, not a repellent, and shows strength, not weakness. Harley learned this during a period of loneliness and anxiety during the pandemic, realizing that honest communication could have alleviated much grief and fostered deeper connections.

What is Harley Finkelstein's closing advice for aspiring entrepreneurs?

Harley advises aspiring entrepreneurs to remember that the cost of failure is currently the lowest it has ever been. This dramatically reduces the risk of trying new ideas. He encourages everyone with an idea, big or small, to 'try it,' as many successful companies started from simple concepts that evolved over time.

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Shopify President: How To Become A Millionaire For The Price Of A Starbucks Coffee! E245

The Diary Of A CEO

People & Blogs4 min read111 min video

May 8, 2023|688,075 views|14,354|678

The Diary Of A CEO steven bartlett steve bartlett podcast the diary of a CEO podcast life lessons CEO

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TL;DR

Shopify President Harley Finkelstein on entrepreneurship, failure, and building a business affordably.

Key Insights

Entrepreneurship is more accessible and affordable than ever, costing less than a few Starbucks coffees.

Failure is a critical part of the entrepreneurial journey, serving as a discovery of what doesn't work.

Passion is important, but survival and a genuine desire to solve a problem are powerful drivers for entrepreneurship.

Self-awareness and focusing on 'spiky' skills, rather than being well-rounded, lead to greater success.

Mentorship is best approached vertically, seeking advice from different people for different life aspects.

The low cost of failure today removes many barriers, making it an ideal time to explore business ideas.

THE ACCESSIBILITY AND AFFORDABILITY OF STARTING A BUSINESS

Harley Finkelstein, President of Shopify, emphasizes a fundamental shift in entrepreneurship: it's no longer an exclusive club. He debunks the myth that starting a business requires significant capital or expertise. In today's digital age, launching a venture can cost less than a few coffees, making it accessible to almost anyone. This democratization is key to Finkelstein's mission of encouraging more people to pursue their entrepreneurial dreams and self-actualize through business creation.

FAILURE AS FUEL AND THE ROLE OF PASSION VS. NECESSITY

Finkelstein reframes failure not as an endpoint, but as a valuable discovery process. He suggests that embracing failure, understanding what didn't work, allows for iteration and improvement. While passion can be a motivator, he highlights that necessity or being driven by hardship, as experienced in his own early life, is an equally powerful, if not more potent, catalyst for entrepreneurial action. This perspective encourages a 'fail fast and learn' mentality.

THE POWER OF SPICINESS AND SELF-AWARENESS IN CAREER GROWTH

A core insight Finkelstein shares is the importance of 'spikiness' – developing deep expertise in a particular area rather than trying to be a generalist. He advocates for self-awareness, understanding one's unique strengths, and doubling down on them. This contrasts with the traditional idea of becoming a 'well-rounded' individual, suggesting that focusing on a few rare and complementary skills creates more value, similar to how Steve Jobs's focus on typography influenced Apple's design.

SKILL STACKING AND THE UNEXPECTED VALUE OF HOBBIES

Finkelstein illustrates the concept of skill stacking through his personal journey, including his experience as a DJ and his use of law school not to become a lawyer, but to develop critical thinking and writing skills essential for entrepreneurship. He also highlights how hobbies, like his wife's ice cream business or his own ventures into tea and ice cream, provide invaluable empathy and practical experience that directly benefits his leadership at Shopify. These seemingly unrelated pursuits can offer unique advantages.

BUILDING RESILIENCE AND FOSTERING AN ENTREPRENEURIAL CULTURE

Shopify's success is attributed to its 'anti-fragile' nature and its culture built by entrepreneurs for entrepreneurs. Finkelstein emphasizes that resilience is a learned trait, fostered by embracing challenges and learning from them. He advocates for companies to invite 'pain' and disruption, as it leads to growth. This is reflected in their 'digital by default' approach, allowing for global talent acquisition while mandating in-person team 'bursts' to maintain strong connections and foster a culture where entrepreneurs want to be.

MENTORSHIP, TRIBE-BUILDING, AND NAVIGATING LONELINESS

Finkelstein's mentorship philosophy involves seeking guidance vertically, finding different experts for different aspects of life, and building a 'tribe' of peers facing similar challenges. He acknowledges the inherent loneliness in the entrepreneurial journey, exacerbated by remote work, but stresses the importance of rituals and consistent connection, whether through formal mentorship or informal peer groups. He encourages vulnerability as a strength, a magnet for connection, and a key to navigating life's inevitable difficulties.

THE INVESTOR'S MINDSET AND BACKING FOUNDERS

When considering investing, Finkelstein looks for creators leveraging their audience to build better products, niche specialists creating best-in-class offerings, and innovators making quality accessible to the masses. He prioritizes founders with resilience, optimism, and a strong mission – individuals who would pursue their venture regardless of financial reward. He believes these 'surfboard people,' who actively embrace challenges, are the ones most likely to succeed and create lasting value.

PRIORITIZATION AND FINDING LIFE'S WORK (IKIGAI)

Effective prioritization, Finkelstein explains, comes from diarizing important personal and professional commitments as 'must-haves' rather than 'nice-to-haves.' This disciplined approach, rooted in identifying one's 'ikigai' or life's work, ensures focus on what truly matters. He emphasizes that the mission of a company should deeply resonate with an individual's own life purpose, allowing them to contribute their best work and find fulfillment, rather than simply pursuing a role for status or compensation.

VULNERABILITY AS STRENGTH AND THE HARDEST CHALLENGES

Finkelstein shares personal struggles, including loneliness during the pandemic and the professional challenge of transitioning roles, highlighting that vulnerability is a strength, not a weakness. He admits to making the transition harder by not speaking up sooner and by feeling he didn't have 'permission' to struggle. He advocates for open communication about goals and challenges, viewing vulnerability as a magnet that fosters connection and builds stronger relationships, both personally and professionally.

THE REALITY OF ENTREPRENEURIAL FAILURE AND WORK ETHIC

Addressing a common misconception that his ventures have always been successful, Finkelstein reveals numerous business failures, including a slipper company and a poker chip company. He stresses that his success stems not from innate genius, but from an intense work ethic and refusal to shy away from difficulty. He encourages aspiring entrepreneurs to emulate this dedication and focus on the journey, acknowledging that true success is hard-won and involves overcoming many setbacks, not just showcasing the final results.

Mentioned in This Episode

●Products

●Software & Apps

●Companies

●People Referenced

Common Questions

Harley Finkelstein, President of Shopify, aims to get more people to become entrepreneurs and self-actualize through building businesses. He believes that the world is more colorful when individuals commercialize their hobbies and find their life's work.

Topics

Skill Stacking

Mentioned in this video

Products

Beast Burgers

Burger chain founded by Mr. Beast, an example of a creator-led brand that improved upon existing fast-food options.

Kylie Cosmetics

Makeup brand founded by Kylie Jenner, highlighted as an example of a creator building a successful product by improving existing offerings.

Feastables

Chocolate bar brand by Mr. Beast, further illustrating creator-led product development from personal passion.

People

Seth Rogen

Artist whose interview Harley listened to as part of his research and preparation, demonstrating his work ethic.

Companies

Supreme

Lifestyle brand, a 'Moby Dick' target for Shopify due to their challenging flash sales, which test and improve Shopify's infrastructure.

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