Harley Finkelstein (Shopify): Keys to Entrepreneurial Success in 2025

Summary:

Harley Finkelstein, President of Shopify, shares his insights on entrepreneurship.
Finkelstein discusses his background and early entrepreneurial ventures [00:01:08].
Emma Grede and Finkelstein explore the decreased cost of failure and the accessibility of entrepreneurship today [00:03:36].
They discuss commonalities among successful entrepreneurs, including grit, expanding total addressable market (TAM), and meeting customers where they are [00:08:13].
Finkelstein emphasizes the importance of story, mission, and authenticity in building a brand [00:15:30].
He also highlights the shift towards building an audience first and then creating a product around their needs [00:19:52].
Finkelstein and Grede delve into what's required for brands to stay relevant and scale without losing their soul [00:36:12] [00:40:58].
Finkelstein gives his advice and action items for aspiring entrepreneurs [01:28:22].

Harley Finkelstein talks about how you have to keep going through the failures to win. [ 00:09:00 ]

Harley Finkelstein's Origin Story [00:01:08]

He describes his background as the child of a Hungarian immigrant who came to Canada in 1956.
He grew up surrounded by entrepreneurs, due to his family using entrepreneurship as a means to provide for themselves.

In 1876, John Womaker created WMakers department store, one of the first department stores in America. To sell products there, one had to convince a retail buyer.
Historically, entrepreneurship had barriers to entry such as money or people.
Now, anyone can be an entrepreneur because there are no more gatekeepers and the cost of failure is almost zero.
Entrepreneurs should surround themselves with people who encourage their ambition.
Entrepreneurs should focus on expanding their TAM, not just taking a slice of the pie.

Grit and Perseverance: Most successful entrepreneurs have a history of failures but persevere.
Expanding TAM: Successful entrepreneurs believe they can grow the market itself rather than just take a slice of the existing pie.
Omni-channel Approach: Selling on every surface area where the consumer spends time, rather than being limited to online or offline channels.
Empathy: Understanding who your customers are and tailoring experiences to them is essential.

A great origin story or founding story matters as it carries the consumer along on the journey.
Selling a mission or idea is more powerful than selling widgets, as consumers want to be part of something bigger.
Founders have an advantage over professional managers because they have a story to tell.
Authenticity is key; entrepreneurs can ask their audience for opinions to involve them in the process.

Today, it's more effective to start with an audience and then build a product around their needs.

To stay relevant, brands must always be willing to change what they do. They have to be willing to always look for new categories.
A healthy disrespect for the status quo matters.
The most important things for the modern entrepreneur are story, values, and how you make people feel.

They give up too early due to the negative connotations of failure.
They do not surround themselves with people that are these force multipliers of your ambition.
The people around them have a negative mindset that pulls them down

Harley describes that as people gain experience, they transition from being a "jack of all trades" to a "triple threat," and eventually to a "spiky object," excelling in a specific area.
Harley has a team to do the things he does not do as well, like being a CTO, is a "spiky object" himself and excels at what he does.
When creating a team, think of it as assembling The Avengers.
They are all so different, and each of them individually have these very spiky objects.

Entrepreneurship is about building something deeply meaningful, more people are recognizing it.
The "velocity" is unbelievable in today's market, meaning that one can reach an incumbent level faster.
Today, it is the best time in the world to start a business.

First thing in the morning: Meditate.
Last thing before bed: Kiss his wife.
Killing it business: Ember Mugs.
Harley aspires to be a worldclass storyteller.
Books: Rich Dad Poor Dad by Robert Kiyosaki, Antifragile by Nassim Nicholas Taleb.
What Harley values that he didn't 20 years ago: Peace.