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

May 8, 2023 1h 49m 17 insights
Harley Finkelstein, President of Shopify, discusses entrepreneurship as a tool for self-actualization, emphasizing its accessibility and the low cost of failure. He shares personal stories and insights on building resilient companies, cultivating unique skills, and the importance of self-awareness and vulnerability in leadership.
Actionable Insights

1. Embrace Anti-Fragility

Actively invite challenges and ‘pain’ into your company or personal life, as systems that are anti-fragile rebuild themselves stronger, better, and faster after being broken or tested. This approach leads to continuous improvement and resilience.

2. Reframing Failure as Discovery

Adopt the mindset that ‘failure is the discovery of something that didn’t work.’ This perspective shifts focus from personal failure to learning, allowing you to extract valuable insights for future attempts and iterate more effectively.

3. Cultivate Spiky, Unobvious Skills

Instead of striving to be well-rounded, focus on going deep and sharpening one unique, ‘spiky’ skill that is complementary to your main field but not obvious. This creates an arbitrage opportunity, making you a rare and valuable talent.

4. Prioritize with Your Calendar

Schedule all ‘must-have’ activities, both professional and personal (e.g., family time, exercise, mentorship calls), into your calendar and commit to them. This practice ensures that important priorities are consistently addressed rather than trying to fit them in reactively.

5. Seek Vertical Mentorship

Instead of seeking one all-encompassing mentor, identify different individuals who excel in specific ‘verticals’ or aspects of life (e.g., parenting, marriage, business). This allows you to gather specialized advice and build a diverse support system.

6. Vulnerability Builds Strength

Embrace vulnerability with trusted friends, family, and colleagues, as it shows strength, not weakness, and is a magnet for connection. Sharing your struggles and goals can foster accountability and deeper relationships.

7. Start Small, Remove Expectation

Begin your entrepreneurial journey by commercializing a hobby or a small idea, removing the expectation of immediate massive success. The low cost of failure and lack of pressure allow for experimentation and stumbling forward, often leading to unexpected growth.

8. Entrepreneurship is Accessible

Recognize that starting a business today is incredibly inexpensive, often costing less than a few coffees, and doesn’t require a formal business plan or prior experience. The cost of failure is at an all-time low, making it easier to try and iterate.

9. Build Diverse Founding Teams

When starting a company, partner with individuals who possess complementary skill sets, rather than those who are just like you. This enriches the team’s capabilities and creates a more robust foundation for innovation and problem-solving.

10. Leverage Hobbies for Business

Explore commercializing your hobbies or using them to gain valuable insights and empathy for customers. These ‘Sunday afternoon activities’ can lead to unexpected business ideas and make you a more effective leader by understanding product functionality firsthand.

11. Deep Customer Empathy

Maintain a deep empathy for how your customers use your product, focusing on their journey from small beginnings to potential large-scale success. This approach ensures you build solutions that add disproportionate value at every step, fostering loyalty.

12. Do It Better, Not Just Different

When faced with competition, focus on executing your idea better than existing solutions, rather than solely trying to be novel. Superior execution and a commitment to continuous improvement are key differentiators for long-term success.

13. Therapy for Self-Awareness

Consider therapy as a ‘hack’ to accelerate self-awareness and personal growth, especially for entrepreneurs dealing with underlying drivers like trauma or insecurity. Find the right therapist, as fit is crucial for effective progress.

14. Foster Resilience in Teams

Actively build a culture of resilience by hiring entrepreneurial individuals who embrace challenges and view them as opportunities for growth. Encourage a ‘surfboard people’ mindset where teams proactively ride the waves of change.

15. Find Your Entrepreneurial Tribe

Seek out groups of people at a similar stage in their entrepreneurial journey, even if in different industries, to share experiences, tactics, and support. Online platforms like Reddit or YouTube comments can be valuable resources for finding these communities.

16. Create Personal Rituals

Establish consistent personal rituals (e.g., family dinners, morning routines) that provide structure, connection, and meaning in your life. These rituals are crucial for well-being, especially in a world that often optimizes against natural connection.

17. Be Honest About Effort

Counter the misconception that success comes easily by openly sharing the hard work, preparation, and failures behind your achievements. This transparency inspires others, sets realistic expectations, and combats imposter syndrome.