Invest Like The Best
Episode 294 Building the Entrepreneurship Company
Invest Like The Best

Episode 294: Building the Entrepreneurship Company

Invest Like The Best

Episode 294

Building the Entrepreneurship Company

Harley Finkelstein is the President of Shopify. We cover the different dimensions of entrepreneurship, the most interesting trends in e-commerce today, and the lessons learned from Shopify's transition to public markets.

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[00:02:26] - [First question] - His interpretation and definition of a person’s life's work 

[00:05:50] - The story of the riverstone and the average polished executive 

[00:08:36] - The thing he can’t help but do; and focusing on our compulsions

[00:13:12] - How he would boil things down to the most simple entrepreneurial formula

[00:16:38] - What is harder and easier about new business formation today 

[00:21:03] - The countervailing forces for small-to-medium business entrepreneurship 

[00:24:31] - What he’s learned about operationalizing ideas and mentor lessons

[00:29:08] - A piece of fortune cookie advice that he finds terrible

[00:30:49] - His philosophy on marketing distribution  

[00:35:27] - The most effective distribution strategies he’s seen work in Shopify that might be portable to other businesses

[00:38:43] - What it was like getting their first app developer for the Shopify app store

[00:41:17] - The state of ecommerce today writ large and what trends are interesting 

[00:45:46] - Lessons learned about the digital places that people are buying 

[00:49:06] - What it’s been like as an executive working at a company that had their stock price explode over the pandemic 

[00:52:25] - Tips for communicating effectively with Wall Street

[00:54:14] - An investor that stands out in memory that really impressed him

[00:55:10] - Important aspects of his world that are worth mentioning 

[00:57:04] - Lessons learned about motivating people through DJing 

[00:59:12] - Whether or not reading the crowd can apply to business

[01:03:49] - The kindest thing anyone has ever done for him

Building the Entrepreneurship Company

Introduction

Patrick
My guest today is Harley Finkelstein. Harley is the president of Shopify and has been with the company since its early years. He's a lawyer by training, but an entrepreneur by calling, and that is the focus of our discussion. We discussed the different dimensions of entrepreneurship and Shopify's role in promoting it, as well as exploring the company's transition to public markets, and what the last few years have been like. Please enjoy my discussion with Harley Finkelstein.

Finding Your Life's Work

Patrick
So Harley, maybe the place to begin is with a term that I and my team have spent a lot of time thinking about and trying to define, which is this notion of life's work amongst entrepreneurs. Obviously, you can be doing your life's work outside of a business, and there's lots of people that do with great outcomes, but our specific interest is what does it mean for an entrepreneur to be doing their life's work? Is it something that's there at the beginning? Is it something that's developed after the fact when they come to realize that they're enjoying their work? Trying to really define this concept, which I think can be an unbelievable fuel for a durable enduring business franchise is of great interest to me. Given that you've been doing what you've been doing at Shopify with Tobi for so long and I think are doing your life's work or would say you are, I'd love to hear your interpretation of this term, whether or not you think it's as powerful as I do, and if so, what the definition or dimensions of it are to you.

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