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Harley Finkelstein

👤 Person
446 total appearances

Appearances Over Time

Podcast Appearances

Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53

He knew that he wanted to put food on the table or had to put food on the table, had to put a roof over the heads of my father and my grandmother and my father's siblings. And so entrepreneurship wasn't this, what it is today, which is follow your dreams, build something with great desire and passion, something with great meaning. He was passionate about surviving.

Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53

He knew that he wanted to put food on the table or had to put food on the table, had to put a roof over the heads of my father and my grandmother and my father's siblings. And so entrepreneurship wasn't this, what it is today, which is follow your dreams, build something with great desire and passion, something with great meaning. He was passionate about surviving.

Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53

not passionate about the entrepreneurial venture themselves. And so I think the fortunate opportunity that I had was my parents didn't look at entrepreneurship as a luxury, as this creative outlet. They viewed it as a way to solve problems because that's what they saw their parents using it for as well.

Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53

not passionate about the entrepreneurial venture themselves. And so I think the fortunate opportunity that I had was my parents didn't look at entrepreneurship as a luxury, as this creative outlet. They viewed it as a way to solve problems because that's what they saw their parents using it for as well.

Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53

So I finished undergrad college and a mentor of mine, I've always had really great mentors in my life since I was a kid. Usually the group of mentors each has one, I don't know, call it a superpower that I really want to copy or really want to emulate. What I realized was there is no one person that exists on the planet who I want to copy the entirety of them.

Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53

So I finished undergrad college and a mentor of mine, I've always had really great mentors in my life since I was a kid. Usually the group of mentors each has one, I don't know, call it a superpower that I really want to copy or really want to emulate. What I realized was there is no one person that exists on the planet who I want to copy the entirety of them.

Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53

But I like one aspect of what they do. I like the way they parent. They're great mom or dads. Or they're great spouses. They have a great relationship with their wife or husband or their life partner. They're in incredible shape. They get to do crazy athletic challenges. Or the way that they articulate themselves is so interesting and so compelling. So I had a mentor of mine who convinced me that

Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53

But I like one aspect of what they do. I like the way they parent. They're great mom or dads. Or they're great spouses. They have a great relationship with their wife or husband or their life partner. They're in incredible shape. They get to do crazy athletic challenges. Or the way that they articulate themselves is so interesting and so compelling. So I had a mentor of mine who convinced me that

Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53

Well, the t-shirt business was a good business that that wasn't ever going to lead to having a large enough impact. And the t-shirt business was a good business, but it wasn't going to change an industry. It wasn't going to allow me to build something that I really wanted to build, which is something that is multi-generational and incredible. And he convinced me to apply to law school.

Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53

Well, the t-shirt business was a good business that that wasn't ever going to lead to having a large enough impact. And the t-shirt business was a good business, but it wasn't going to change an industry. It wasn't going to allow me to build something that I really wanted to build, which is something that is multi-generational and incredible. And he convinced me to apply to law school.

Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53

The idea was... I should apply to law school not to become a lawyer, but rather to become a better entrepreneur. And he was a lawyer, and he thought that law school would be like finishing school for me as an entrepreneur. I'd learn how to write and think and articulate myself and do all these things that maybe I didn't really have at that particular time when I was in college.

Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53

The idea was... I should apply to law school not to become a lawyer, but rather to become a better entrepreneur. And he was a lawyer, and he thought that law school would be like finishing school for me as an entrepreneur. I'd learn how to write and think and articulate myself and do all these things that maybe I didn't really have at that particular time when I was in college.

Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53

And he happened to be teaching law school at the University of Ottawa. And so I applied to one law school. It was just the University of Ottawa. I applied there, took the LSAT, fortunately got in, and I moved to Ottawa in 2005 to begin law school.

Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53

And he happened to be teaching law school at the University of Ottawa. And so I applied to one law school. It was just the University of Ottawa. I applied there, took the LSAT, fortunately got in, and I moved to Ottawa in 2005 to begin law school.

Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53

And I realized when I got there that this t-shirt business was never going to survive because ultimately it requires me going and meeting these student council people that were buying t-shirts face-to-face. My entire unfair advantage was I was selling t-shirts to students as a student myself. The business model just broke if I had to go to class.

Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53

And I realized when I got there that this t-shirt business was never going to survive because ultimately it requires me going and meeting these student council people that were buying t-shirts face-to-face. My entire unfair advantage was I was selling t-shirts to students as a student myself. The business model just broke if I had to go to class.

Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53

In law school, you actually have to attend class unlike undergraduate or college where you can just show up for the exams. So I moved to Ottawa in 2005 and wanted to meet people. I wasn't really becoming friends with people in law school. They were very serious. They wanted to be lawyers and they were very studious. I was an entrepreneur.

Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53

In law school, you actually have to attend class unlike undergraduate or college where you can just show up for the exams. So I moved to Ottawa in 2005 and wanted to meet people. I wasn't really becoming friends with people in law school. They were very serious. They wanted to be lawyers and they were very studious. I was an entrepreneur.

Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53

I was a lot more interested in the value extraction from the curriculum of law school. I didn't care about doing well on the exam. I cared about selfishly, you know, it's like an exchange. I'm giving the law school $10,000 or $15,000 per year in tuition. In return, I'm demanding $10,000 or $15,000 worth of value. And so I didn't get caught up in grades and exams because I wasn't why I was there.

Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53

I was a lot more interested in the value extraction from the curriculum of law school. I didn't care about doing well on the exam. I cared about selfishly, you know, it's like an exchange. I'm giving the law school $10,000 or $15,000 per year in tuition. In return, I'm demanding $10,000 or $15,000 worth of value. And so I didn't get caught up in grades and exams because I wasn't why I was there.