[05:58] How far back does Tobi’s obsession for optimization go?
[08:14] How big is Shopify today?
[09:13] How did Tobi and I first meet?
[11:45] From my perspective, Shopify is a living example of what happens when the good guys win.
[12:31] Did Tobi’s early authority problems lay the groundwork for his current success?
[18:57] Something Tobi and Seth Godin agree on: the current characteristics of a temporary solution shouldn’t be mistaken as the ultimate objective.
[20:25] Even though you probably didn’t learn about him in history class, here’s how entrepreneur Malcolm McLean changed the world.
[23:13] A few of the books Tobi has found indispensable for finding footing in the business world.
[26:55] As a self-described slow reader with dyslexia, Tobi has to be selective with the books he takes in. By what criteria does a book make it to Tobi’s “to read” list?
[29:50] How Tobi’s role at Shopify changed from passionate programmer to reluctant CEO, and how he rose to the challenge to crash course his way through the learning process.
[36:05] When pitching to VCs on Sand Hill Road, this is how Tobi rolls (literally).
[37:36] Good and bad decisions Tobi made as a fledgling CEO.
[39:31] As a man whose expectations for employees match what he expects from himself, is Tobi difficult to work for?
[44:12] How does Shopify company culture facilitate the thick skin required to abide by Crocker’s Rules?
[47:37] Feedback is a gift.
[48:56] How the Enneagram system is used at Shopify as an empathy exercise rather than a personal horoscope.
[50:30] How can a growth (versus fixed) mindset — per psychologist Carol Dweck’s work — be fostered?
[55:24] Tobi’s definition of Hell.
[58:03] How Scott Adams’ “talent stacking” applies to Tobi’s career trajectory.
[1:03:08] Tobi addresses the factors that contribute to an underreported entrepreneurship crisis.
[1:08:39] How Shopify’s annual Build a Business competition came about, what it aims to accomplish, and some of the hurdles it has faced along the way.
[1:15:43] The first Build a Business winner and how its success was boosted by a happenstance presidential endorsement.
[1:17:39] The fascinating patterns, principles, and stories we observe every year when Build a Business time comes around.
[1:23:49] Does dyslexia affect Tobi’s coding?
[1:24:12] In search of an extended sense of peace? Here’s a book recommendation.
[1:25:59] What Tobi means by “the next box.”
[1:30:18] What Tobi learned about the next box from Jürgen, his mentor.
[1:33:37] Is it possible to understand the box you currently occupy and aim for the box you want to occupy next?
[1:34:37] In what box does Tobi see himself at the moment?
[1:35:38] How does Tobi choose ways to stress test possible exits from his current box?
[1:36:50] We examine the reasons behind Tobi’s discomfort with comfort on a business level in spite of generally considering himself “the most fortunate person on the planet” on a personal level.
[1:40:21] On identifying himself as the bottleneck that held back Shopify for a period of time, what caused this, and what Tobi is doing to ensure he doesn’t take on this unenviable role again.
[1:42:35] Why does Tobi think the business not only survived this period in the bottleneck, but actually began to thrive?
[1:47:44] Increasing “luck surface area” and staying in touch with the front lines by getting in the trenches from time to time.
[1:49:13] How Shopify’s chief investor from the early days still helps Tobi focus on what’s important — by ensuring he’s not “meddling” in minutiae.
[1:51:54] Though the future is admittedly uncertain, here are two things Tobi believes a forward-looking CEO can do to peek into what seems most probable.
[1:54:05] Is modern China showing us tomorrow today?
[1:55:00] What can the massively successful but mostly ignored video game industry teach the business world about the human psyche?
[1:57:18] What would Tobi’s billboard say?
[1:57:49] What books does Tobi most frequently gift?
[2:00:01] What is the Adlerian separation of tasks?
[2:00:52] Why Tobi believes we, as a society, need to celebrate and support entrepreneurship now more than ever.
[2:03:00] What cities does The Oracle of Ottawa believe are doing the best job of taking business into the future?
[2:04:32] Parting thoughts.