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Tobi Lütke: Calm Progress

Nov 15, 2022 2h 42m 44 insights
My guest today is Shopify co-founder and CEO Tobi Lütke.  We discuss the differences between founders and professional managers, how he’s scaled with Shopify, the constant fight against bureaucracy, how he thinks about innovation in a large company, and how he manages to keep his head when everyone else is losing theirs.   A coder at heart who emigrated from Germany to Canada two decades ago, Lütke co-founded the e-commerce giant Shopify in Ottawa in 2006. The Globe and Mail named Lütke "CEO of the Year" in November 2014,  and in May 2021 the company reported that it had more than 1.7 million businesses in approximately 175 countries using its platform. As of July 2022, Shopify is among the top 20 largest publicly traded Canadian companies by market capitalization, and the company’s total revenue for 2021 was $4.611 billion. Lütke previously appeared on Episode 41 of The Knowledge Project.   --   Want even more? Supporting Members get early access, hand-edited transcripts, member-only episodes, and so much more. Learn more.   Every Sunday, our Brain Food newsletter gives you a mental edge in 5 minutes with timeless insights you can use. Add it to your inbox.   Follow Shane on Twitter.   Our
Actionable Insights

1. Protect Your North Star

During volatile times, focus on protecting the overall strategy and north star (the reason a company exists), rather than getting sidetracked by current tactics, to navigate obstacles while maintaining direction.

2. Rethink Roadmaps & Plans

Instead of rigid roadmaps, have a clear guide view of what matters to your merchant, a strong model of your company’s capabilities, and continuously rerun the function of deciding the very best thing to work on, allowing teams to pick the next task as needed.

3. Practice Subtraction Relentlessly

Founders and leaders should focus on subtraction, removing things that no longer make sense or are less effective, because it’s much easier to add than to remove, preventing accumulation of unnecessary complexity and maintenance work.

4. Embrace Differentiated Work

Avoid doing the same thing everyone else does; instead, use all your learned knowledge to create something as good as possible, as following “best practices” is often a way to avoid risk and leads to undifferentiated work.

5. De-Risk Failure Internally

Companies should provide psychological safety for internal failure, reframing underperformance as “successful discovery of something that did not work” and an opportunity to gain more data and try again.

6. Innovate Across All Disciplines

Strive to innovate across all disciplines and groups within a company, encouraging every team to find ways their approach is better than general industry implementations through first-principle thinking.

7. Derive Business from Programming

Re-derive all business practices from programming principles, applying concepts like resilient systems design, auditable functions, data processing, observability, and unit tests to business models and operations.

8. Define Your Infinite Games

Reflect on and define your personal “infinite games” (journeys with no end goal, like fitness or self-mastery), and align your life decisions and finite games (tasks with specific goals) with these overarching purposes.

9. Welcome Change in Infinite Games

Cultivate an attitude where change is welcome and clarifying, especially when pursuing an “infinite game,” as new information helps you adapt and continue the journey rather than ending the game.

10. Prioritize Long-Term Decisions

When making decisions, consider what the company in 10 years would wish you had done, prioritizing long-term benefits and predictable secondary/tertiary effects over short-term expediency or ease.

11. Remove Bad Ambiguity

In times of significant change, remove ambiguity quickly by clearly communicating decisions and their implications, even if they are difficult, to help people plan and adapt.

12. Focus on Core Value

Maintain composure by understanding your inherent value comes from your brain, choices, experience, skill, and intuition, not external accreditations or job titles, and focus on being valuable and flexible.

13. Opt for Skill Range

Most people should opt to develop a range of skills and knowledge across multiple fields, as the ability to learn new things quickly (learning as a skill) allows for competence in many areas.

14. Integrate Engineering Thinking

Integrate engineering thinking and systems design principles as the core of your decision-making, applying lessons learned from building resilient systems to all aspects of business and leadership.

15. Use Humor Against Bureaucracy

Use humor to address silly or ineffective processes, making fun of them as a way to identify and replace them with something better.

16. Design Aligned Systems

Design company systems so that individual intelligent actions and local incentive systems align with society-level benefits, mission, and overall company goals, minimizing bureaucracy.

17. Centralize Strategic Decisions

Foster a culture where ideas, actions, and proposals are omnipresent from everyone, but strategic decisions are made from the perspective that best understands the long-term goals of the business.

18. Simplify Compensation Systems

Implement a simple compensation system where everyone receives a clear annual number, allowing individuals to choose how they want to receive it (cash, stock options, etc.), treating people like adults who can make their own choices.

19. Replace Toil with Technology

Use technology to replace toil, drudgery, and “bullshit” jobs, freeing creative people to contribute more significantly when enabled with proper tools.

20. Prioritize User Experience (UX)

Prioritize User Experience (UX) as a fundamental equalizer that makes technology and its benefits available and approachable for everyone.

21. Leverage Tools as Multipliers

Recognize that tools, especially technology, act as multipliers of human ability, not mere additions, enabling individuals to achieve vastly different and greater results.

22. Learn Programming Quickly

To learn programming, dedicate focused time (e.g., a weekend) to online resources like Khan Academy, as it’s more accessible and quicker to pick up useful skills than often perceived.

23. Question Sleep Beliefs

Challenge and correct unhelpful beliefs about sleep (e.g., feeling drowsy means bad sleep, needing exactly eight hours), as these stories can negatively impact your sleep experience.

24. Practice Strict Bed Hygiene

Strictly limit activities in bed to only sleeping; avoid bringing phones, reading, or doing anything else in bed to condition your brain to associate the bed solely with sleep.

25. Go to Bed When Sleepy

Only go to bed when you feel genuinely sleepy, rather than at a set time, to improve sleep onset and quality.

26. Address Middle-of-Night Waking

If you wake up in the middle of the night and are wide awake, get out of bed, go to a nearby chair, and read for 15 minutes until you feel sleepy again, then return to bed.

27. Use Sleep Trackers

Use a sleep tracker (e.g., Oura Ring, Apple Watch) to gather data about your sleep patterns, which can be useful for understanding and improving sleep.

28. Explore CBT for Insomnia

For insomnia, explore Cognitive Behavioral Therapy for Insomnia (CBT-I), which has a high effectiveness rate comparable to or better than sleeping pills, by reading books or using apps.

29. Re-evaluate Travel Necessity

Re-evaluate the necessity of extensive travel, especially for routine meetings, as much of it can be a “tax” on spending time with people and can be replaced by more deliberate, focused interactions.

30. Build Trust Batteries

Build a “trust battery” by working collaboratively, making key decisions as a team, listening to all perspectives, but ultimately ensuring that a clear decision-maker is responsible for the final choice.

31. Leverage Transformer Models

Pay attention to transformer models in machine learning, as they are causing significant breakthroughs and accelerating progress in various fields.

32. Explore Open-Source AI

Explore open-source AI models like Stable Diffusion, recognizing their profound impact on human creativity and the rapid acceleration of progress they enable through community contributions.

33. Stay Optimistic on Crypto

Maintain optimism about valuable innovations emerging from the crypto world, especially after cycles that shed speculative “froth.”

34. Challenge Inconvenient Facts

Embrace the idea that “facts are friendly,” even when connections or effects are inconvenient for the main story you tell yourself, and be willing to re-evaluate positions based on new data.

35. Review Decisions Periodically

For important decisions, capture the rationale and inputs, and revisit them periodically, rerunning the function over evolving inputs to adapt to a changing world.

36. Seek External Expertise

When facing a problem, ask “who in the world is good at this, and what can I learn from them?” to find effective solutions and avoid common pitfalls.

37. Understand Sentiment vs. Reality

Be aware of the “I’m great, but everything else is fucked” effect, where individual optimism contrasts with perceived societal pessimism, and understand that sentiment often tracks actual experience differently.

38. Embrace Useful Models

Embrace the concept that all models are wrong, but some are useful, and apply this thinking to decision-making, understanding that you often have to make choices with incomplete information.

39. Don’t Wait for All Inputs

Do not wait for 100% of inputs before making a decision, as you will never have them; instead, make choices when necessary and later review how well you gathered relevant inputs.

40. Manage Archetypes Deliberately

Be deliberate about where you place conformist or aggressive conformist archetypes within the company, as they play important roles in some groups but can hinder innovation if misapplied.

41. Prioritize Mission Clarity

A clear, well-understood mission statement provides a reason for existence, clarifies purpose for everyone, and can rally people together, especially during challenging times.

42. Consider Second/Third Order Effects

Develop an intuition for secondary and tertiary effects of decisions, recognizing that while primary effects are often the focus, deeper consequences can have significant societal impact.

43. Avoid “Trust Fall” Management

Avoid the “trust fall” approach of simply hiring smart people and getting out of their way; instead, actively engage in important decisions, working alongside teams to leverage your perspective and make things happen faster.

44. Recognize Computation’s Impact

Understand that breakthroughs in computational speed and efficiency fundamentally change what is possible, leading to rapid progress across many domains.