Harley Finkelstein - Building the Entrepreneurship Company - [Invest Like the Best, EP.294]

My guest today is Harley Finkelstein. Harley is the President of Shopify and has been with the company since its early years. He is a lawyer by training but an entrepreneur by calling and that is the focus of our discussion. We discuss 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. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [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; Distilled [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] - How Brands Grow; 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