Moment 130 Shopify's President The 1 Skill You MUST Have To Thrive In Business Harley Finkelstein

Summary Notes


In a conversation with the host, entrepreneur and Shopify executive Harley Finkelstein discusses the concept of 'spikiness'—leveraging unique and complementary skills to excel in entrepreneurship. Drawing from personal anecdotes, including advice from mentor Philip Reimer and his own law school experience, Finkelstein emphasizes the importance of skill stacking and the pursuit of unorthodox education to sharpen one’s business acumen. He illustrates this through his diverse experiences, from DJing to assisting his wife's ice cream business, and even starting a tea company during the pandemic. These pursuits, while seemingly unrelated, provided him with invaluable insights and empathy, making him a more effective leader at Shopify. Finkelstein advocates for starting businesses with complementary partners, experimenting with ideas, and embracing the learning process without the pressure of immediate success.

Summary Notes

Concept of Spikiness in Career Development

  • Spikiness refers to the idea of focusing on one's unique strengths and abilities in a career.
  • It suggests doubling down on what you are good at rather than trying to improve in areas where you are weak.
  • The concept encourages finding and cultivating a distinctive edge or 'spiky point' that sets you apart in your field.

"You referenced spikiness. You know, you said you. And that gave me flashbacks to a conversation I had with Jimmy Carw where he said, we don't need more people that are shit at physics, find the thing you're good at, and, like, double down there as career advice for an entrepreneur or someone that's not an entrepreneur."

This quote introduces the concept of spikiness, emphasizing the importance of recognizing and investing in one's strengths rather than trying to be mediocre in everything. It sets the stage for the discussion on how this concept applies to entrepreneurship and career development.

The Role of Education in Sharpening Entrepreneurial Skills

  • Education, such as attending law school, can be used strategically to gain skills that enhance entrepreneurial capabilities.
  • The speaker's mentor, Philip Reimer, advised using law school as a means to gain a sophisticated skill set for business rather than to practice law.
  • The idea was to absorb information and insights from law school to become a more sophisticated entrepreneur.

"He basically convinced me to go to law school, and he convinced me to go to law school, not to become a lawyer. He's like the skill set that you need. Given what I think your ambitions are around business creation, business building, entrepreneurship, you are lacking some sophistication."

This quote explains the mentor's advice to use law school as a training ground for entrepreneurship rather than as a pathway to a legal career. It highlights the value of a law education in developing a sophisticated understanding of business and entrepreneurship.

Utilizing Unique Skills as Competitive Advantage

  • The speaker discusses the idea of finding a unique skill or knowledge area that competitors might not possess.
  • This unique aspect can be seen as an alpha or arbitrage opportunity in entrepreneurship.
  • The speaker's own experience with law school provided him with writing, negotiation, and critical reasoning skills that were not common among entrepreneurs but valuable for his career.

"So when you leave law school, you can return to entrepreneurship in a much better version of yourself because you'll have something that the competitors said other entrepreneurs wouldn't have."

The quote underlines the competitive advantage gained from pursuing an unorthodox path like law school for an entrepreneur. The skills and insights acquired are unique compared to what other entrepreneurs might have, providing a distinct edge in the business world.

The Importance of Identifying and Focusing on One's Spiky Point Early

  • Recognizing one's spiky point early in a career can guide decision-making and career development.
  • The speaker reflects on how identifying his interest in entrepreneurship shaped his choices from a young age.
  • Understanding the personal significance of entrepreneurship allowed the speaker to make strategic decisions that aligned with sharpening his spiky point.

"I think the sooner you figure out that spiky point, you don't have to be precise. I didn't know I was going to run a software company, but I knew that entrepreneurship was deeply important to me."

This quote emphasizes the value of early identification of one's spiky point, even if it's not fully defined. It suggests that having a general direction or area of focus can significantly influence one's career trajectory and success.

Skill Stacking in Industry

  • Skill stacking involves combining multiple, complementary, and often rare skills within an industry.
  • The concept suggests that being in the top 10% in six complementary skills can make someone the best in a field among a large population.
  • This approach is contrasted with focusing solely on improving a single, more common skill.
  • Examples given include Cristiano Ronaldo, who is not the best in any single football skill but is highly rated across several, and Steve Jobs, who combined knowledge of typography and design to create beautiful devices.
  • The recommendation for someone like Jack, who records podcasts, is to acquire rare but valuable skills that could set him apart, such as storytelling, theater, set design, or DJing.

I think we should go through this in a little bit more detail because I think it can really have a profound impact on people.

This quote emphasizes the importance of discussing skill stacking and its potential significant impact on individuals' careers.

If Jack wanted to be a podcast director, what all podcast directors or producers do is they'll go learn how to do microphones and cameras. Now, interestingly, I don't think that's the place to be placing your time to become the best in the world.

The speaker suggests that acquiring common skills like handling microphones and cameras might not be the most effective way to stand out as a podcast director.

Complementary Skills and Business Partnerships

  • The idea of starting a company with people who have different skill sets is emphasized.
  • It is recommended that individuals seek out partners from different faculties, such as Arts or Philosophy, rather than sticking to those with similar backgrounds.
  • Complementary skills can lead to a richer set of abilities and potentially more successful partnerships.
  • The speaker, Philip Reimer, reflects on how his experience as a DJ taught him valuable lessons applicable to running a large public company.
  • Establishing a good relationship with clients or counterparts before formal interactions can lead to more favorable outcomes, as trust and common ground are established.

Most people start companies with people just like them. Yeah, most people start companies with people that they would have been friends with in high school. I think that's a terrible idea.

Philip Reimer advises against forming business partnerships solely with like-minded individuals, suggesting that diversity in skills and perspectives is more beneficial.

In fact, if you are in college right now, listening or watching this, and you're in the business program, commerce, or you're in the engineering program, don't start a company with the person sitting next to you. Walk across the street, go to a different faculty, go to the Faculty of Arts, or go to the faculty of Philosophy, or go to faculty of engineering and find someone there to start a company with.

Philip Reimer encourages students to seek out partners from different academic backgrounds to enhance the diversity of skills within a startup.

If the pre meeting went really well with the client, no matter how the party went, it was going to be a great result, because if I had a good relationship or good connection with the client, even if half the party didn't want to dance, the client knew me and knew enough about me and knew that I was going to try my best, that even if half the party was dancing, they were happy about.

Philip Reimer shares his insight from DJing that having a strong pre-existing relationship with a client can lead to positive perceptions of performance, regardless of actual outcomes.

Understanding and Adapting to the Audience

  • The importance of reading the audience's reactions to tailor music selection.
  • The skill of gauging audience engagement and adjusting accordingly.
  • Implementing creative strategies to encourage audience participation without direct requests.
  • The application of DJing skills in managing public companies.

"So one of the things about djing you have to do is you have to read the audience."

This quote emphasizes the critical skill of audience perception in DJing, which is applicable in broader management contexts.

"Oh, they really like this song. Great. I'm going to go like, mo money, mo problems from Torius B-I-G and the whole crowd erupts."

The quote illustrates the immediate feedback loop between the DJ and the audience, guiding the DJ's next move to maintain engagement.

"Instead have something in the middle of the dance floor that people want to see."

This quote suggests using indirect methods to draw people in, demonstrating a strategic approach to achieving desired outcomes.

The Value of Hobbies and Curiosity

  • The significance of hobbies and external interests in providing inspiration and clarity in one's primary work.
  • The tendency to undervalue hobbies when focusing on primary business goals.
  • Encouraging a holistic view of personal development and its impact on professional success.

"What I've heard from that is our hobbies and the things and the curiosity we have outside of the area that we're building in is equally important."

This quote highlights the integral role of hobbies in contributing to creativity and perspective in one's main professional endeavors.

"Taking a step away from the painting allows us to see the picture a bit clearer and also to create that picture a bit clearer."

The quote uses a metaphor to explain how distance from work can enhance vision and creativity.

The Concept of a Polymath

  • Defining a polymath as someone knowledgeable in various fields.
  • The advantage of having diverse interests and knowledge bases.
  • The application of polymathic qualities to business and leadership.

"A polymath is someone who knows a lot about a lot of different things."

This quote defines the term "polymath" and sets the stage for discussing its relevance in business and personal growth.

Practical Learning from Hobbies

  • The real-world business skills gained from supporting a spouse's ice cream business.
  • Developing empathy for entrepreneurs through hands-on experience.
  • Personal growth and coping strategies discovered during the pandemic.
  • Launching a tea business as a hobby to explore and understand Shopify's features.

"My wife started an ice cream company in 2016... that was super valuable because, one, it built huge empathy for the people that you shop that are starting out."

The quote underscores the empathetic understanding and business acumen gained through close involvement with a family business.

"I was drinking so much more coffee... I'm going to replace your coffee with really great green tea."

This quote reflects a personal change that led to the creation of a tea business, demonstrating how personal experiences can lead to new ventures.

"Both those things have made me, as a leader at Shopify, so much more valuable."

The quote connects the speaker's hobbies to professional development, showing the practical benefits of diverse interests.

Overcoming the Fear of Starting a Business

  • The psychological barrier of starting a business is compared to looking up at Mount Everest.
  • The fear stems from the perceived need for substantial money, a team, product sourcing, logistics, branding, and immediate success.
  • Success is often equated with making a large amount of money, which can be a daunting expectation for new entrepreneurs.

"When I think about starting a business, like a tea business or any business, I'm stood at the bottom of Mount Everest looking up, thinking, Jesus Christ, like, I've got to find a website... Who's going to work for me? Where do I get the tea from? How do I send it in the post? What's the packaging? I need to do branding and I need to do it all now."

This quote encapsulates the overwhelming feeling that potential entrepreneurs may experience when considering all the components and challenges of starting a business.

The Power of Starting Small

  • Emphasizes the importance of starting with a passion and without the pressure of it becoming more than a hobby.
  • Suggests that removing expectations and time frames can lead to more successful business ventures.
  • Encourages entrepreneurs to start with small, manageable steps and to allow the business to evolve naturally over time.

"Remove the expectation, which Sir David Brailsford told me about really well, just remove the expectation of you ever being anything more than a hobby and just get going and you'll stumble forward along the way and that's okay."

This quote highlights the advice given by Sir David Brailsford about reducing pressure by not expecting the business to be anything more than a hobby initially, which can lead to more organic growth and learning.

The Entrepreneurial Journey in Modern Times

  • Many successful businesses on platforms like Shopify start without a formal business registration and with minimal initial investment.
  • The modern entrepreneurial landscape has reduced the cost of failure, making it less risky to try out new business ideas.
  • The best time to start a business might be during school or as a side hustle due to lower expectations of success.

"Most people on Shopify don't register their business until weeks after they sign up for Shopify. So most people don't even assume they're going to need to register a business. And that's okay."

This quote indicates that many Shopify users begin experimenting with business ideas before formally establishing a company, suggesting a trend of informal and exploratory business development.

Celebrating Small Wins and Reducing Pressure

  • Small achievements in the early stages of a business are celebrated, which encourages continued effort.
  • The lack of scrutiny over financial metrics like revenue and EBITDA margins in the initial stages can alleviate pressure on new entrepreneurs.

"You sell one, everyone clap."

This brief interjection by Speaker A underscores the importance of celebrating even the smallest successes when starting a business, which can be a morale booster and motivation to keep going.

Accidental Success Stories

  • Many successful Shopify businesses began unintentionally and grew from simple ideas or dissatisfaction with existing products.
  • Examples include FIGS, Gymshark, and Allbirds, which all started from a desire to improve existing offerings in their respective markets.
  • Long-lasting, impactful businesses are often not the result of extensive business plans but rather from curiosity and exploration of a core idea.

"Most of the businesses on Shopify that are really successful, the homegrown success stories, they were accidental... That's not how businesses are created in modern times."

This quote by Philip Reimer illustrates how many successful businesses on Shopify started by chance and grew out of a desire to solve a problem or fill a gap in the market, rather than from a detailed business plan.

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