Tobi Lütke — From Snowboard Shop to Billion-Dollar Company (#359)


“Feedback is a gift.” — Tobi Lütke

Tobi Lütke (@tobi) is the founder and Chief Executive Officer of Shopify. In 2004, Tobi began building software to launch an online snowboard store called Snowdevil. It quickly became obvious that the software was more valuable than the snowboards, so Tobi and his founding team launched the Shopify platform in 2006. He has served as CEO since 2008 at the company’s headquarters in Ottawa, Canada.

Tobi is an active advocate for computer literacy and education, and serves as a board member of Canada Learning Code, an organization working to give all Canadians access to digital skills. In 2014, Tobi was named The Globe and Mail‘s CEO of the Year. He served as Chair of the Digital Industries Table, an advisory board commissioned by the federal government to provide recommendations on how to turn Canada into a digital leader.

Please enjoy!

Listen to the episode on Apple Podcasts, Spotify, Stitcher, Overcast, Castbox, or on your favorite podcast platform.

You can find the transcript of this episode here. Transcripts of all episodes can be found here.

Want to hear the story of a go-getter who launched his now seven-figure business on Shopify? — Listen to my conversation with SpyGuy’s Allen Walton in which he describes how he made the switch from overworked and under-appreciated employee to entrepreneur (stream below or right-click here to download):

#351: Real 4-Hour Workweek Case Studies — Allen Walton and SpyGuy, The Path to Seven Figures

This podcast is brought to you by Peloton, which has become a staple of my daily routine. I picked up this bike after seeing the success of my friend Kevin Rose, and I’ve been enjoying it more than I ever imagined. Peloton is an indoor cycling bike that brings live studio classes right to your home. No worrying about fitting classes into your busy schedule or making it to a studio with a crazy commute.

New classes are added every day, and this includes options led by elite NYC instructors in your own living room. You can even live stream studio classes taught by the world’s best instructors, or find your favorite class on demand.

Peloton is offering listeners to this show a special offer. Visit and enter the code TIM at checkout to receive $100 off accessories with your Peloton bike purchase. This is a great way to get in your workouts, or an incredible gift. Again, that’s and enter the code TIM.

This episode is also brought to you by LegalZoom. I’ve used this service for many of my businesses, as have quite a few of the icons on this podcast — such as Automattic CEO Matt Mullenweg of WordPress fame.

LegalZoom is a reliable resource that more than a million people have already trusted for everything from setting up wills, proper trademark searches, forming LLCs, setting up non-profits, or finding simple cease-and-desist letter templates.

LegalZoom is not a law firm, but it does have a network of independent attorneys available in most states who can give you advice on the best way to get started, provide contract reviews, and otherwise help you run your business with complete transparency and up-front pricing. Check out and enter promo code TIM at checkout today for special savings and see how the fine folks there can make life easier for you and your business.

QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

Scroll below for links and show notes…


  • Connect with Tobi:

Website | Twitter | LinkedIn

  • Connect with Shopify:

Shopify | Twitter | Instagram | Facebook | YouTube


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


Posted on: February 7, 2019.

Please check out Tribe of Mentors, my newest book, which shares short, tactical life advice from 100+ world-class performers. Many of the world's most famous entrepreneurs, athletes, investors, poker players, and artists are part of the book. The tips and strategies in Tribe of Mentors have already changed my life, and I hope the same for you. Click here for a sample chapter and full details. Roughly 90% of the guests have never appeared on my podcast.

Who was interviewed? Here's a very partial list: tech icons (founders of Facebook, Twitter, LinkedIn, Craigslist, Pinterest, Spotify, Salesforce, Dropbox, and more), Jimmy Fallon, Arianna Huffington, Brandon Stanton (Humans of New York), Lord Rabbi Jonathan Sacks, Ayaan Hirsi Ali, Ben Stiller, Maurice Ashley (first African-American Grandmaster of chess), Brené Brown (researcher and bestselling author), Rick Rubin (legendary music producer), Temple Grandin (animal behavior expert and autism activist), Franklin Leonard (The Black List), Dara Torres (12-time Olympic medalist in swimming), David Lynch (director), Kelly Slater (surfing legend), Bozoma Saint John (Beats/Apple/Uber), Lewis Cantley (famed cancer researcher), Maria Sharapova, Chris Anderson (curator of TED), Terry Crews, Greg Norman (golf icon), Vitalik Buterin (creator of Ethereum), and nearly 100 more. Check it all out by clicking here.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

Comment Rules: Remember what Fonzie was like? Cool. That’s how we’re gonna be — cool. Critical is fine, but if you’re rude, we’ll delete your stuff. Please do not put your URL in the comment text and please use your PERSONAL name or initials and not your business name, as the latter comes off like spam. Have fun and thanks for adding to the conversation! (Thanks to Brian Oberkirch for the inspiration)

19 comments on “Tobi Lütke — From Snowboard Shop to Billion-Dollar Company (#359)

  1. Hey Tim,

    Thoroughly enjoy your podcast and the guests you have. It has been enjoyable to say the least. Whenever I was listening to certain episodes regarding psychotropic medicines I could not help to thank about Wade Davis. Have you attempted to have him on an episode? It would be great considering his proximity to a significant amount of early western research.


  2. Just wanted to share with you how much I enjoy your Podcasts. I listen to them during my commute and find the topics and interviews fascinating.
    Keep up the good work!


  3. Dear Tim,

    you probably hear “thank you” so often that it might lose its emphasis, but I cannot understate how valuable your podcasts are for me. I feel an inner sense of peace when listening to your podcasts, probably because I feel deeply understood.

    I especially love the nuances in how you’re doing your interviews, following your own curiosity and deepening the conversation, being so present with your interviewee. The way you connect things and what you share about yourself often makes me think: That’s just like me. And realise: I can do even better. Actually, I name your podcast as one of the main resources in learning how to cope with ADHD – paradoxically most great resources don’t name ADHD explicitly very often (too bad!), but are detailed descriptions of one’s own experiences that others can draw from – and your podcast is just a goldmine for that.

    Most of all, I wanted to say: Thank you.



  4. “Feedback is a gift ”
    It was great to listen another inspiring story about Toby. Thanks to Tim and team who made this possible.


  5. As a fellow Canadian and German I am so happy that Tobi has found the success he has. His mindset, way of thinking and attitude toward life is something to be celebrated. There are not may folks is his position that are as humble as he is. Tobi leads by example. Let that be an example to us all. Clearly I am a fan-boy (don’t mind admitting it).


  6. Among many favourite quotes from this podcast, I’ll pick: “Failure … we call it the successful discovery of something that did not work.” Really enjoyed this one, so had to comment and forward it to a friend or two who are starting or running small businesses. – Thanks!


  7. Love Crocker’s Rules – hadn’t heard of it before – but very useful. And love your work. It has been more helpful than you could imagine!


  8. Hi Tim,

    Thanks for another awesome and inspiring podcast!

    I was wondering if you’d be interested in doing business here in Brazil. I’ll be honored in talking to you 🙂

    Best regards


  9. I really enjoyed on this interview with Tobi. I myself is from Canada. I really like his attitude on the optimization methods that catapulted to his present day success with Shopify. I hope i listen to more podcast to inspire me on my online business pursuit.


  10. An inspiring guy.
    Said a few things that made an immediate impact on me.
    The one about Hell being meeting what you could have been just before you die. That seems a lot more encouraging than the usual, “you only have one life” mantra.
    The other one was what he said about getting your own cellphone made in a day in Shengzen.
    Make one wonder what is really possible. Most folk never see the kind of stuff that puts those ideas in their heads. Such is the value of these podcasts.
    I’d love to hear more of this guys thoughts.
    It’s also nice to know that folk like this are looking after my Shopify store……..


  11. A megapisode.
    Tobi’s analogy around the self-awareness of the box you’re in was profound. And, I had the notebook out to jot “Hell is meeting the best version that you could have become, at the end of your life”. And, glad to hear Tim reference “Awareness” as mentioned in the Peter Mallouk episode. After one-clicking it to Kindle, I had to buy a hard copy too this last week…


  12. Tim, I second all the positive responses here, and also wanted to say I find it somehow inspiring that you too are a Six on the Enneagram. I share some of your scepticism about it (naturally), but admire greatly how you’ve triumphed over the doubt and anxiety inherent to our Type which can be such huge impediments to success.