YouTube2h 36m· Nov 2022· cataloged

Tobi Lütke: Empowering a World of Rebels | Knowledge Project Podcast


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The Knowledge Project Podcast - 152 with Tobi Lütke - Calm Progress (https://fs.blog/knowledge-project-podcast/tobi-lutke-2/)

Celebrated entrepreneur and Shopify co-founder and CEO Tobi Lütke discusses how Shopify endured through the COVID-19 pandemic, why he’s so optimistic about the future, the differences between founders and CEOs, how his job has changed as Shopify has grown over the years, how to fight bureaucracy, how he thinks about innovation in a large company, and how he manages to keep his head when everyone else is losing theirs, among other topics.

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00:00 - Intro 01:04 - How to lead through troubles 03:05 - Maintaining focus through chaos 09:33 - CEO vs. founders 18:28 - Taking risks 24:50 - On hiring vs. promoting talent 31:13 - How to fight bureaucracy in a company 40:36 - How Tobi thinks about compensation 46:03 - What businesses can learn from programming 01:01:42 - Why Tobi loves technology 01:04:37 - On leveraging technology 01:08:17 - Does tech make us more productive? 01:13:50 - On accurate vs. useful ideas 01:16:30 - On identity and status 01:22:56 - How to stay calm through the chaos 01:27:33 - How Tobi thinks about second and third-order effects of decisions 01:38:22 - Rapid grants 01:41:07 - “Future-forecasting” decisions in a company 01:47:36 - Tobi’s thoughts on conformity 01:54:06 - Tobi’s thoughts on the Infinite Game 02:06:46 - How Tobi fixed his sleep 02:18:03 - What Tobi used to spend time on that’s now wasteful 02:25:45 - What technology Tobi is most excited about

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0.75

Learning speed itself is a learnable skill; people who have developed good learning habits can pick up new fields much faster than the average person, which means the real skill distribution is around 'how good are you at learning' rather than 'how much do you know'.

factualhigh valueestablishednovelty 2/4durability 3/4· Tobi Lütke

Specialists will like everyone who knows that there should be a specialist no space should you know like it's like everyone should be in specialist now they should be like this is this is a very particular set of character traits um which wants to dedicate itself to a [very narrow kind of thing] what Specialists don't understand is like how how incredibly good journalists can be at at 50 things right like they think like a bit many people figure journalists is sort of like a jack of [all trades master of non-legates] this is one of the dumbest sentences I've ever heard that's like not like that's just usually someone who hasn't made a choice and is not good at developing any any kind of like a very fairly rare people um um uh you you like Pareto Principle and no one tells you but first 80 of every field can be done 20 of time so like you you can you can you end up easily five Fields um for uh in uh to to a degree of eight out of ten um what other specialist is just looking at [primary topic] right so um and frankly this is even incorrect because people know learning the next thing is significantly faster than learning previous thing because with skilled set of learning is itself a skilled set and it's actually your skill set of how quickly you are learning which determines how long it takes you to pick up any kind of New Field to to a certain head or 10 out of 10.

0.75

Computer science was historically marginalized in universities and placed in basements because it did not fit into existing disciplinary structures; it was treated as a practical tool rather than a fundamental field, similar to how a physics department might treat engineering.

factualhigh valueestablishednovelty 2/4durability 3/4· Tobi Lütke

where did everyone put them if you actually I I'm I'm well through the books that Chronicle the history even though it was our obscure [books that are] un like more people have to read um it's always a basement of some building click work a rental off campus across the street from the MIT or Harvard or something like this where they put people um because it didn't fit into anything right

0.75

Cognitive Behavioral Therapy for Insomnia (CBT-I) is more effective than sleeping pills (90%+ efficacy vs. lower efficacy and dependence risk) but is severely under-available (only ~100 certified practitioners in the US) and under-promoted, despite being one of the most important health interventions available.

factualhigh valueestablishednovelty 2/4durability 3/4· Tobi Lütke

CBT-I is a sub part of that called insomnia it's actually it's all correctly named but actually it's it's correct Han I think the taxonomy is correct so um finding out by this exists I tried finding a doctor for it I couldn't um because uh there's only like I think all of the United States is a hundred certified um people have been doing it since the 90s um Effectiveness rate is 90 is better at sleeping pills

0.74

Revision to the mean (entropy) is the default state for companies; bureaucracy, best practices, and process sediment all pull organizations toward the ambient industry competency level, which is typically mediocre, and the only way to fight this is through constant subtraction and strategic focus.

causalhigh valueestablishednovelty 1/4durability 4/4· Tobi Lütke

what happens is uh revision to the meal right like it's it's uh the tragedy of a comments uh is is is the active ingredient entropy you can call it like all these things describe the same thing they all affect companies um um we're a department or the tech company reverts to the sort of middle of a bell curve ambient industry competency um uh for everything it does um that's like really bad because ambient industry or like Orthodox quality is just quite low um uh on it just it just is

0.72

When you say yes to something, you actually say no to every other thing you could have done with that period of time, so adding things gradually makes the set of things that can be done smaller while the set of things that must be maintained grows larger, eventually leaving most people working on maintaining the status quo rather than innovating.

causalhigh valuecontestednovelty 2/4durability 4/4· Tobi Lütke

if you say no to a thing you say no to one thing if you say yes to a thing you actually say no to every other thing you could have done the first period of time and so as people are adding things um the the set of things that can be done it becomes smaller and smaller smaller and a set of things that has to be maintained gets larger and larger and larger

0.71

In large organizations, aligning individual incentives with organizational mission requires designing systems where people's local efforts naturally level up to systemic benefit; this is difficult because there is inherent tension between individual incentives and collective outcomes.

factualhigh valueestablishednovelty 2/4durability 3/4· Tobi Lütke

you do the same thing I hope in a in a microwave in the company right like it's uh you know like this if you are um in a company everyone is allowed and actually encouraged to be an intelligent actor in their own sort of local and Center sister um the system should be designed so um that people sort of individualistic um efforts level up to the society level benefits

0.70

All models are wrong but some are useful; the key skill is not finding the perfectly accurate model but finding the model with the right level of abstraction for the decision at hand and being able to assess whether you had enough information to make a good choice.

definitionhigh valueestablishednovelty 1/4durability 4/4· Tobi Lütke

I mean this is like a reoccurring topic that you I think teach extremely well like what concept of like all models I use uh are wrong but some are useful like yeah I just like it's it's a right way to think like I think this is another one of those things that you learn um um in engineering adjacency

0.69

Sleep quality is not well-understood by most people; common beliefs (like needing 8 hours, or that waking up feeling drowsy means bad sleep) are incorrect; actual sleep needs vary by individual and can be determined by looking at historical sleep data.

factualhigh valueestablishednovelty 1/4durability 3/4· Tobi Lütke

I had bad stories that I taught myself like such as if I wake in the morning up in the morning and I feel drowsy I had a bad night's sleep that's incorrect it's like that just means you you woke up in a [different part of a sleep cycle] right I need eight hours of sleep I don't I I in fact you can I think if you if you've spent enough times forgetting to church whoever was you probably have enough data to figure this out

0.69

One of the biggest challenges of leading a large innovative company is building psychological safety for people to take risks, learn from failure, and redefine failure as 'successful discovery of something that didn't work' rather than career-ending mistakes.

factualhigh valueestablishednovelty 1/4durability 3/4· Tobi Lütke

it's a successful discovery of something that didn't work if if you underperform it's it's we know actually more data and we um um uh they'll try again it's uh people actually a performance mashed out euphemism um to um if I don't take risks um so it's it's actually for your career a job fair is actually more risky too um not aim high and I think that environment um and with psychological safety to take [this risk is very hard to produce

0.69

Second and third-order effects of decisions are often hard to predict and much more consequential than first-order effects, but most decision-makers only consider primary effects, making strategic decisions difficult.

factualhigh valueestablishednovelty 1/4durability 3/4· Tobi Lütke

Secondary effects are very very um hidden on opaque of all I think Governor wrote a lot more than people realize um um very very often the secondary effects are and and tertiary effects are um are vastly more of societal impact and the primary effects

0.69

People often derive their value and self-worth from their job title or role rather than from their actual capabilities and contributions; this creates fragility because changing roles feels like a loss of identity rather than an opportunity to develop new capabilities.

factualhigh valueestablishednovelty 1/4durability 3/4· Tobi Lütke

a lot of people end up getting really invested in their sort of job title as an identity and um um they think they are valuable because the job is valuable unfortunately so much of a bird is like is is kind of is a second order effect of of self-confidence issues um people seem to have a fairly low opinion of themselves fundamentally

0.68

Stock options and equity compensation exist largely because of historical tax optimization, not because they are the best way to align incentives; in many jurisdictions (like Canada), there is no tax advantage, yet equity compensation persists, suggesting path dependency rather than rational design.

causalhigh valuecontestednovelty 2/4durability 3/4· Tobi Lütke

a lot of stock options and others use these things are exist because it's a tax optimization system very often it's not actually true anymore in many places like in in either Canada has a different tax system never had really uh stock options in most places actually bears in some instances now coming which is sort of interesting I think Germany is creating some tax favorability for stock options um and um so so like the world is very different um I think these things should be available but not prescribed

0.68

Best practices are actually just average risk-adjusted practices; they encode the wisdom of conventional wisdom and discourage deviation, but innovation requires doing things differently, and therefore taking on risk that best practices explicitly avoid.

causalhigh valuecontestednovelty 2/4durability 3/4· Tobi Lütke

best practices actually just simply means don't take risk and do with what everyone else is saying you should be doing um best practices are not that black good there should be best no their average risk adjustments yeah exactly it's just average and um I don't think I have no time for average

0.68

Environmental movements' historical opposition to nuclear power created a secondary effect: by reducing nuclear capacity, they made the world more dependent on coal and natural gas, which increased carbon emissions, leading to the very climate change they were trying to prevent.

causalhigh valuecontestednovelty 2/4durability 3/4· Tobi Lütke

a lot of our carbon issue introvert comes from uh the environmentalists convincing the world that is involving we're building a um economy that required Luca power we could somehow do it with colon Instead [and] um the oil now I think we got the scorecard for that this really worked very poorly um and I don't I still think it's an expense but pad of needed to run but like we did and um um until maybe a year ago it seemed like we actually were really not looking at this um because service I mean what I should make this explicit this secondary effect of us not building nuclear power plants is but now we have climate change right so um primary effect is environmental movement secondary effect is climate change

0.68

Academia is poorly designed for society's interests because it incentivizes narrow specialization and theory over practical problems; progress from academia has slowed too much for the amount of resources devoted to it, and founder-led academic institutions might be needed to drive reform.

factualhigh valuecontestednovelty 2/4durability 3/4· Tobi Lütke

I I I I I and I wish maybe we would have more founder-led academic institutions that could engage in some redesigns and their subtractions or figure out some different means by which we could enable some good thinkers of when legitimacy needed to make some changes there because otherwise we are just going to get paper citing papers and rings and and um I I think procus has from Academia is like slowed down too much for given the amount of sort of like off like 50 resources

0.65

The key to fixing insomnia is understanding that sleep comes when you are sleepy (not tired), and the way to build sleep hygiene is to only go to bed when sleepy, create a bedside reading chair for when you wake up and can't immediately fall back asleep, and stick to a consistent sleep schedule.

normativehigh valueestablishednovelty 1/4durability 3/4· Tobi Lütke

you cannot sleep when you're just fatigued and not sleepy but you can always sleep when you're sleepy um so what to do from it on an effective [basis] is uh you you do create this routine a lot of these tools are useful um you uh but and this is the hardest part you do not do basically that's some minor allowances anything in your bed better specific it's you see you'll be your best for sleeping you have a chair close by uh that's you take your book there um you would read there um you do not bring your phone to bed ever

0.65

Specialists develop extraordinarily deep expertise in narrow domains, while generalists can develop 80% competence across many fields much faster than becoming 100% expert in one; the Pareto Principle suggests most fields can be learned to 80% in 20% of the time required for 100%.

factualhigh valueestablishednovelty 1/4durability 3/4· Tobi Lütke

Specialists will like everyone who knows that there should be a specialist no space should you know like it's like everyone should be in specialist now they should be like this is this is a very particular set of character traits um which wants to dedicate itself to a [very narrow kind of thing] what Specialists don't understand is like how how incredibly good journalists can be at at 50 things right like they think like a bit many people figure journalists is sort of like a jack of [all trades master of non-legates] this is one of the dumbest sentences I've ever heard that's like not like that's just usually someone who hasn't made a choice and is not good at developing any any kind of like a very fairly rare people um um uh you you like Pareto Principle and no one tells you but first 80 of every field can be done 20 of time

0.64

Risk in business is most often not about taking bold action but about inaction or following best practices; the real risk is strategic obsolescence that comes from doing the same thing as everyone else, which only becomes apparent when you fast-forward time.

causalhigh valuecontestednovelty 2/4durability 3/4· Tobi Lütke

it is actually risky to not take uh if I try higher but like I a lot more people have it's not risky in the moment though right to to follow best practices it's only risky as you fast forward time yeah and I mean we should acknowledge why if you make like if you do what everyone else does you are like say like well that's what industry does um if you make an edit to it you are you will have a responsibility go to bed for for that change um at least that's it from if you risk avoidant this is something you don't you don't want no if of course if it works it's great

0.64

Stable Diffusion being released as open-source created an acceleration in the field because it enabled developers and practitioners to contribute improvements, not just academic researchers, and it has been getting faster and more efficient through these contributions.

factualhigh valueestablishednovelty 1/4durability 2/4· Tobi Lütke

what what is so profound I think stable diffusion is that it's gotten released as open source and now what's happening with it is just a wants to it's like all acceleration it has but all like this is already the property maybe minus crypto the fastest progressing field in the world and um has just found two or three more gears there because if you track like I mean we started like [I] think first versions on top of a line graphics cards on your own machine you can execute this by this open source um you could make an image in 15 seconds I think they're down to three yeah and and like with no Hardware changes and just like well because um the tooling behind machine learning was again it's a very academic field

0.62

Technology IS progress, and if people adopt a pessimistic view of technology, they are adopting a pessimistic view of human progress itself, which is both factually incorrect based on data and also corrosive to optimism and agency.

normativehigh valuecontestednovelty 1/4durability 3/4· Tobi Lütke

if you have the people who do like like um on the airwaves uh you know like every person on the planet ends up becoming oh well everyone becomes sort of average of five people they spend the most time with Fred like that's just sort of a really well documented or oh if it's fundamentally true but it's super useful as if as a as a mental [model] and I think that uh you know one of those people is a media for most people and um um so you're adopting a set of beliefs which are I think extremely colored um and in this particular case I think somewhat unfortunate because you just recast the applied field of human progress as something that is causing detrimental outcomes

0.60

The Turing machine, and by extension all computing, represents something more fundamental to life and human civilization than is commonly appreciated; it is as fundamental as DNA and deserves to be integrated into how we understand human history.

normativehigh valuespeaker onlynovelty 3/4durability 4/4· Tobi Lütke

I think what's the one of the greatest bit bits of like if technology is [progress] the turing machine is the engine of progress and uh that that almost all like net human purpose is going to be built on uh because everything is going to round to zero um and it was probably mainly needed for bootstrapping the turing machine

0.60

Programming synthesizes key properties of mathematics (theoretical purity and abstraction through symbols and equivalence) with practical linguistics, creating a new field that can reason about computable, resource-constrained systems that mathematics alone cannot address.

definitionhigh valuespeaker onlynovelty 3/4durability 4/4· Tobi Lütke

it's it's called a sort of um it's theoretical cohesion a very equivalency sign is like those two sides are exactly the same thing not just reasonably similar um it's it's it's sort of a language but it's actually it doesn't have a concept of abstraction it's like everything is just these formulas picture and um um so you end up with this new word of a turing machine which is actually the midpoint between human language and Mathematics

0.60

Transformer models and large language models represent a breakthrough in making machine learning practical and accessible, allowing millions of people to contribute improvements rather than just academic researchers.

factualhigh valueestablishednovelty 1/4durability 2/4· Tobi Lütke

machine learning has been unreasonably effective already um but why do Transformer models change everything like it's another one of us they've Transformer models feel a little bit more of a vocational than academic and like they're probably not as good an analogy to the brain as maybe some of her other like approaches or at least it's up as puplay as some of them um bad boy back it's crazy what's happening like it's crazy

0.59

The model of 'hire smart people and get out of their way' is not effective; instead, founders should maintain deep involvement in decision-making, maintain what Tobi calls a 'trust battery' with key leaders, and collaborate on important decisions to benefit from diverse perspectives.

normativehigh valuecontestednovelty 1/4durability 3/4· Tobi Lütke

I fell a little bit into this work through org chart treated as a trust for you know like uh hire smart people and then get out of their way I think that's a waste of everyone's time it's not even good for the like it's a nice story but it's like dumb [we have] a um idea of a trust battery that we talked about in previous times you talked about and today about um the trust battery builds we work together we work alongside we make key [decisions] together as a team everyone brings perspective we listen to absolutely everyone but the choice at some point has to be someone's

0.57

The convergence of Transformer models, large language models, and diffusion models is creating possibilities that will define the next era of human capability; this is the most exciting time in technology and requires both theoretical breakthroughs and practical engineering to implement.

forecasthigh valuecontestednovelty 1/4durability 2/4· Tobi Lütke

everything changes every time there's like a significant breakthrough in terms of speed and and and computation because uh like it is extraordinary how many things we can do [with] language large language models and uh diffusion models and Transformers and I I just like I wish I think in a more inspired world yesterday's breakthroughs in the world of stable diffusion would be every single day of the last couple months at the front page news

0.57

All of business should be rederived from programming and systems design principles because programming uniquely solves the problem of building resilient systems that must operate in chaotic, non-deterministic environments with incomplete information.

normativehigh valuespeaker onlynovelty 3/4durability 3/4· Tobi Lütke

I think all of business has to be rederived from programming principles I I had this intuition I think we even had this situation on previous episodes like we talked about this wherever I tried it it worked better and all other approaches

0.57

Legitimacy—the accumulated social credit from an organization's founding story—is a resource that can only be spent by the founder; when a founder leaves, the account remains but cannot be drawn upon, making it impossible for non-founder successors to execute the same kinds of changes.

factualhigh valuespeaker onlynovelty 3/4durability 3/4· Tobi Lütke

if the founders are still there they can still draw on as a count of legitimacy and so my role I see um very often is that um I have the like pretty humbling uh ability to like like use the resources deposited into this uh backup card of legitimacy in the company [you make changes and because I can speak for the entire story of a place yeah now if I would leave Shopify this bank account would only increase but no one could draw on it and therefore it can't be an active ingredient in a company

0.55

The human brain's compute capacity and intuition are more powerful than artificial computers combined, especially for making decisions in the moment with incomplete information; people should be more confident in their intuitive pattern-matching abilities.

factualhigh valuecontestednovelty 1/4durability 3/4· Tobi Lütke

the super computer in our brain is absolutely utterly in support not unsurpassed by auditory machines combined um coming to work to produce everything you've ever seen to make the best decision in the moment

0.54

Tobi is optimistic about the future and believes 'the best is yet to come'; in 20 years, these AI developments will be studied as the formative years of human civilization, when humanity had to ask existential questions about organization and prioritization.

forecasthigh valuecontestednovelty 1/4durability 2/4· Tobi Lütke

The Best is Yet to go it is it's and it's gonna be freaking amazing there is no chance like I'll take a long bet for a lot of money on this if anyone wants to take it [it'll] have to be a real long bet but like if I'm right I'll have to pay out um but for rest of human history but 20 years before this point I mean 20 years after I'm going to be more studied and will be treated as the coming of eight of our species um they are going to be treated as the formative years where we went through the questions we had to ask ourselves

0.53

The quality of a decision is independent of the outcome; a good decision with incomplete information that leads to a bad outcome is still a good decision, while a lucky decision with the right outcome is still a bad decision if it wasn't based on available information.

definitionhigh valuespeaker onlynovelty 2/4durability 4/4· Tobi Lütke

accuracy very often is um picking the right result but that's actually independent of making good decisions uh like that's just that's I think resulting is what poker players call this and I think it's not really the right thing to do

0.53

The Turing machine is not just an abstract mathematical object but represents something analogous to DNA in biology: it is a mechanism that reads and writes to itself, creating more of itself, which suggests computing is more fundamental to understanding life and systems than is commonly appreciated.

factualhigh valuespeaker onlynovelty 3/4durability 2/4· Tobi Lütke

I think what terrain like invented um is a uh his EP um um is not as separate as people make it out to be if you look at the cells that make all life this is kind of what DNA is like it's a it's a read head and the right and the right head and it like it creates more DNA it creates more cells

0.53

Russia's invasion of Ukraine forced Europe to reconsider its energy policies, creating a secondary effect where climate change may actually be solved faster due to the need for energy independence and rejection of fossil fuel dependence—a perverse silver lining to the crisis.

forecasthigh valuespeaker onlynovelty 3/4durability 2/4· Tobi Lütke

Russia invites Ukraine which seems to be a recurring topic here everything in primary is bad secondary effects many many many of them are bad like there's a secondary effect of everyone having to look at the energy policies and realizing holy health should be probably defeat nuclear power plants back so you know we actually um you know in a really odd way um Europe's dependence on Russia for natural gas pipelines Plus the act of aggression by Russia may actually cause climate change to be solved which is like an unbelievable [story]

0.52

Computer science and its practitioners were historically sidelined by academia and industry as a cost center, but the 'revenge of the nerds' is that companies founded on computing principles are now out-performing traditionally managed firms, though the broader public has not yet integrated this into their understanding of why the world is the way it is.

causalhigh valuespeaker onlynovelty 2/4durability 3/4· Tobi Lütke

the Revenge of the nodes is actually that we now build all these companies which have gone out performing everyone else and and and frankly everyone has to kind of understand but that isn't because we can technical skills but actually because we and I'm including myself here in sort of this engineering discipline

0.52

Business systems should be thought of like software systems with explicit models, configurations, and auditable functions that can be tested, versioned, and iterated; this allows organizations to make changes systematically rather than ad-hoc, making them more adaptive to changing conditions.

normativehigh valuespeaker onlynovelty 2/4durability 3/4· Tobi Lütke

I made all of this executable I now go and um just edit one file and then it rebuilds a model of a business I think and then if you like it in a engineering that's sort of engineering thinking company the bat becomes the new desired model and the goal of uh the um HR discipline is actually not to make all these arbitrary decisions but actually to look at what is the model of a company what is the actual state of a [company] whatever moves that gets the actual State as close to the model as possible

0.52

Understanding second and third-order effects can lead to cynicism if one focuses on how perverse incentives and unintended consequences are inevitable; the antidote is to focus on facts and systems thinking while maintaining agency to influence outcomes.

normativehigh valuespeaker onlynovelty 2/4durability 3/4· Tobi Lütke

the danger with secondary advert but tertiary effect thinking his it really lends itself to cynicism um because because um sometimes you see these connections which are like Felix trying out the inconvenient for for for for the main story if you tell ourselves um but I I also think facts are friendly uh I mean I mean and also those are not Factor facts they are like compounding systems

0.52

Applied computational philosophy, combining principles from computer science, systems design, engineering, and other fields, should probably be a core academic discipline with a dedicated faculty, not relegated to 'computer science' departments.

normativehigh valuespeaker onlynovelty 2/4durability 3/4· Tobi Lütke

I think that's completely unappreciated right now as as a source of um business thinking value uh and um uh I find I find it's very very interesting this is really what I mean with applied computational thinking in a applied computational philosophy being almost the higher order [academic department] that should exist on the campus and by way it should probably have the nicest building

0.52

The book 'Why We Sleep' is anxiety-inducing and misleading because it makes unsupported claims about universal sleep requirements and the catastrophic consequences of sleep deprivation, whereas actual data (from modern sleep trackers) shows significant individual variation.

factualhigh valuespeaker onlynovelty 2/4durability 3/4· Tobi Lütke

there's a book which initially I thought was good called why we sleep which is actually very bad um from everything I know now um I I mean it's it's not bad for Coke as incorrect in the macro sense but it gives you it it I think the book itself is anxiety-inducing um because it makes claims on which I don't think prove out on the um importance of sleep and how everyone's goals should be to sleep eight hours and there is no variance

0.52

Professionally managed (non-founder-led) companies tend to excel at operational excellence and quantifiable metrics through careful stakeholder management and planning, but they struggle with subtraction and cannot draw on founder legitimacy to make disruptive changes.

factualhigh valuespeaker onlynovelty 2/4durability 3/4· Tobi Lütke

professionally managed companies are often like the mental picture comes to my mind it's like a river stone right something that's like really smooth around all the edges it's like um there's like it's a very similar uh skill level on everything but usually they're like if they have significant competencies they're often about just operational excellence and uh you're very very quantifiable things um everything that can be measured they tend to be very good at

0.52

The rapid technological change and pace of new infrastructure emergence (internet, mobile, SaaS, broadband all converging in the 2000s) created a Goldilocks zone for startup creation, and this environment has become less favorable now; future entrepreneurship will more often involve extracting great ideas from large innovative companies and applying them to other fields rather than creating entirely new categories.

forecasthigh valuespeaker onlynovelty 2/4durability 3/4· Tobi Lütke

these examples are not coming along at the pace anymore as the early 2000s right like um or you know a lot of a multi-billion dollar companies um uh in in Technologies uh like come from is it a three four five year period of startup creation right which was this extreme Goldilocks zone of um uh everything was changing the mobile SaaS internet uh Broadband um member Broadband folder um all of these things happen at the same time

0.52

The key advantage of the engineering/computing mindset in building large organizations is experience designing systems that must be resilient to chaos and non-determinism, which trains the mind to think in terms of abstraction and model-building in ways that historical business training does not.

causalhigh valuespeaker onlynovelty 2/4durability 3/4· Tobi Lütke

we spent our formative years designing systems that are have to be resilient to like weird non-deterministic like the kinds of things that are even that you can't even really put into a market formula right like the hacket loss and like um and you know our word actually is one of Chaos in which we are trying to pretend that it isn't and then we have to put abstract systems almost in the heritage of linguistics

0.52

Most books and media narratives about history in the last 50 years have not integrated computing and the information revolution into their main narrative; computing remains relegated to a sideshow while the 'real' history is told through political and economic events, but this is an extraordinarily lossy model of what is actually happening.

factualhigh valuespeaker onlynovelty 2/4durability 3/4· Tobi Lütke

I think 120 years from now when we talk about human history um like these books felt like hacker by Stephen Levy and a dream machine and um look code by pets old and you know office kind of these books are actually um going to be referenced books that show the actual Mainline history of our species right and currently we like it's sort of like relegated like the newspapers talk about I mean current affairs which we showed like they are also important but it feels like we are living on this in in this weird word but actually has not integrated its own Mainline history track uh into the public Consciousness

0.52

The widespread pessimism and anxiety about the future and technology, despite objective improvements in life expectancy, poverty, disease, and opportunity, is driven by media consumption patterns; people think they are doing OK but believe everyone else is doing poorly, creating a sentiment-reality gap.

causalhigh valuespeaker onlynovelty 2/4durability 3/4· Tobi Lütke

everyone in the world is like I'm doing great everyone's anxiety is based on their understanding of everyone else which everyone else literally disagrees with like so we all think everyone has to do bad at everything that's getting worse but it isn't like it it's it the numbers don't bear down there's countries I think South Korea was like 9010 like 90 people are doing fine and they're only fake like ten percent think anyone else is okay

0.52

Good decision-makers are not necessarily those who make correct decisions in hindsight, but those who can identify the relevant inputs for a decision, properly weight them, and explain their reasoning in a way that makes the decision obvious in retrospect.

factualhigh valuespeaker onlynovelty 2/4durability 3/4· Tobi Lütke

everyone who looks at the info kind of come to the same I I've actually never really seen this situation where people are truly making different choices like there's always if there are like people on different sides you just have to like okay let's take it from the top and like talk or click State or the unstated assumptions that are actually inputs into decision making and once was uh flushed out it becomes pretty obvious

0.52

Decisions should be revisited periodically as new information emerges and as your understanding of the inputs evolves; maintaining a decision record allows you to assess whether the decision would change based on new evidence.

normativehigh valuespeaker onlynovelty 2/4durability 3/4· Tobi Lütke

and then after you make this decision you don't just if it's an important decision like strategy or something you don't like throw away this entire book you actually capture it and you revisit it because again the world keeps changing and by the way your appreciation of inputs are that you considered end up evolving as well and so you should actually at any moment we run a function over the inputs

0.52

The transition from building companies on old tools (process, story, rules) to building them with computational thinking will make incentive system design more complex but more auditable, allowing companies to move faster while remaining aligned.

forecasthigh valuespeaker onlynovelty 2/4durability 3/4· Tobi Lütke

now with computation impactual Computing I think we can Implement more complex systems that are more auditable be able to provide some of the analysis if things are going in the right direction and so in in a macro sense um and and will actually make it much easier to implement uh in a more complex incentive systems

0.50

The transition from financial optimization of compensation systems (using stock options for tax benefits) to explicit, auditable systems (clear salary + choice of how to receive it) represents applying engineering thinking to HR, making it more transparent and adaptable.

factualhigh valuespeaker onlynovelty 2/4durability 3/4· Tobi Lütke

so I mean we switched to a very simple system where everyone gets a number this is what you make every year and um so everyone agrees but like the ground truth is of compensation and then you can say we want this in cash do you want visit stop options um uh and there's going to be other things like uh so like we will hopefully get to a place where you can use uh like like we have currently I think two or three sliders but you can uh choose how you want your conversation and then like they're hopefully will be 10 or so to get as we build more capacity for different options

0.50

Founder-led companies are often described as immature, but this is incorrect; they are instead 'spiky objects' with very strong aptitudes in specific areas (often matching the founder's strengths) and sometimes surprising weaknesses, but organized around solving a particular set of problems.

factualhigh valuespeaker onlynovelty 2/4durability 3/4· Tobi Lütke

in a in a way where you have Riverstone on one side you really have sort of a sort of volcanic ash kind of spiky object thing um of a rock on the other side like they like some have very very strong aptitudes spiky object sometimes surprising weaknesses it's it's not a well-rounded thing in Rand but it's usually perfectly appropriate in terms of well an ideal case it's appropriate in its aptitudes for the um a particular set of problems that the company a company serves

0.50

The ability to subtract—to remove products, initiatives, and people—is one of the most valuable and rare capabilities a founder can provide to a company, but it requires bravery and legitimacy and can be done perhaps 10-100 times more easily by founder-led CEOs than by professionally managed ones.

factualhigh valuespeaker onlynovelty 2/4durability 3/4· Tobi Lütke

what does office mean well the best thing Founders can do with subtraction this is surprising but like it's it's the the reason like it's much much much easier to add things um than it is to uh to to to to remove um things um adding things is a lot more expensive than removing things actually um uh however it requires some measure of bravery

0.50

Innovation should happen everywhere in a company, not just in product R&D; every function—from HR compensation systems to sales processes—should be reimagined from first principles, and the best acquisitions are those that bring in ideas that can be adapted and improved rather than replacing internal innovation.

normativehigh valuespeaker onlynovelty 2/4durability 3/4· Tobi Lütke

I think every group in a company should be able to go to a conference and talk about how we are doing like how our group is better than sort of a general implementation of this discipline or idea um and by us doing things differently and how you're thinking about this first principle thinking applied to uh any area can can yield huge upside and um I mean ideally that I think the best uh like like a way I would like that to see this is actually that for our own purposes to build the best company that supports it being extremely Innovative for entrepreneurs in the retail space um we are innovating across all the disciplines

0.50

The proper framework for evaluating a decision is to ask: given the information available at the time, was this a good decision? If information was available but not considered, that is a failure of due diligence. If information was unavoidable and the decision was still wrong, that was acceptable risk-taking.

definitionhigh valuespeaker onlynovelty 2/4durability 3/4· Tobi Lütke

my my test interpreter is always like wherever any 20 minutes I could have spent to pull this piece of information I didn't consider right into the set of things I uh used as inputs to make the decision if so I wasn't equal to the task of making the choice at the time and I need to um understand this better in the future and approve for

0.50

Tobi's role now and in the future will be to understand possibilities created by computing, test them, and contribute to the historical record by participating in exploring what becomes possible; being a 'custodian and explorer' of computing's possibilities is his fundamental contribution.

normativehigh valuespeaker onlynovelty 2/4durability 3/4· Tobi Lütke

the like there's no chance you would want to live through any different times if a future is fantastic and will probably become [immortal] relatively soon and all these kind of things um and um maybe not us but our children they think well uh and and so um a lot of what people will be preoccupied with in the future is clearly what's what's next and what's possible and many of the biggest questions will remain to be studied and and to guide our curiosity but like it's here where it all was like pop on the table and it was being wounded the world thing and I just [it] seems it seems so incredibly great to be around to be able to study this stuff it's so fantastic to go and um actually be a public like play a tiny little role like make the title Dent into it

0.48

Media institutions have a grudge against technology because they have been negatively affected by it, but this is a mistake; new media forms (podcasts, founder-operated video, newsletters) are thriving and this is actually a Golden Age of media, not a decline.

causalhigh valuespeaker onlynovelty 1/4durability 3/4· Tobi Lütke

because media I mean a media has a crutch against technology for frankly understandable reasons like um everyone in media works for an institution that probably was negatively affected by Tech now I think media [itself] like if you if you trip some out it's actually doing great like podcasts are doing great like um a builder operated founder operated videos killing it

0.48

Excessive business travel pre-pandemic was treated as a marker of commitment and sincerity despite being destructive to family relationships and personal health; this was a form of unnecessary 'penance' that should not return.

normativehigh valuespeaker onlynovelty 1/4durability 3/4· Tobi Lütke

I think um I think it's hugely Pro um spending time with people and I think travel is a um instead of a text on doing this which is totally like easily worth it um but I think there was a lot of trouble before that um pandemic I think which was almost like I don't know feels like it was almost Penance for meetings like it's just like hey there like it's like your sincerity had to be proven at some kind of altar of sincerity by you sacrificing uh days of travel and airports and cross-continent travel um and compromising your time with your children

0.47

Shopper's new compensation system gives employees a transparent base salary and then lets them choose how to receive additional value (cash, stock options, and potentially other instruments), treating them as adults who can make informed choices rather than using complex financialized derivatives that obscure the actual value exchange.

factualhigh valuespeaker onlynovelty 2/4durability 3/4· Tobi Lütke

we switched to a very simple system where everyone gets a number this is what you make every year and um so everyone agrees but like the ground truth is of compensation and then you can say we want this in cash do you want visit stop options um uh and there's going to be other things like uh so like we will hopefully get to a place where you can use uh like like we have currently I think two or three sliders but you can uh choose how you want your conversation

0.47

Bureaucracy is not inherently bad; it is often a set of checks and balances that exist for good reasons (preventing rodents, in the wall metaphor), but the problem is that bureaucracy often lacks perspective hierarchy—a hole in a wall might need to be papered over locally, but at a higher level it might need structural repair, and at an even higher level the wall might be irrelevant.

factualhigh valuespeaker onlynovelty 2/4durability 3/4· Tobi Lütke

see a hole in a wall and what you would try to do is paper over it which might make perfect sense in the in in the sort of local context that you have but actually if you the next person with a larger perspective says actually we we use driver patches um because that doesn't cause problems of rodents and um the person like if they talk to the next person they say you know what that wall that this hole is actually bad for it shouldn't be there let's actually get rid of entire walk

0.47

Tobi has applied engineering skills and systems thinking to business strategy and organizational design, which he previously thought would not work, but has found they are surprisingly effective and represent a convergence of his engineering background with business leadership.

factualhigh valuespeaker onlynovelty 2/4durability 3/4· Tobi Lütke

now I have a um idea of a trust battery that we talked about in previous times and I'm doing [it] I'm not putting engineering skills on speed dial anymore they are now the core of how I make decisions and I I I I just that's been just a fascinating like if I [could] travel back in time like and just give this as a hey this is this will happen I wouldn't but I would be extraordinarily surprised by this I I really was almost in a like hey I this skills took me here they will not take me there I actually need to go for a full change of identity and just like embrace me looking for strategy and like a bit more of a sort of old school things a bit [um] I thought this is gonna work it's blown up in my like I think it can work in peace time uh I think it cannot

0.45

Shopify shifted from all-office to permanently remote ('digital by design') because the input variable changed (people could not go to offices) and when you re-ran the decision function, the new logic led to a new policy, which was communicated early to reduce ambiguity for employees.

factualhigh valuespeaker onlynovelty 1/4durability 3/4· Tobi Lütke

I did that with I decided we built a lot of offices we did them extremely well I think they got very good at building offices but then a change happened in a world and and one of the variables was like well can are people allowed to go to it like like uh for officers I don't think I had that that was an unstated input that wasn't a stated input but it was one we won't get flipped we decided like okay no offices anymore

0.45

Tobi now sleeps exactly 6.5 hours per night (his personal average) and can fall asleep in ~5 minutes with 95% sleep efficiency, having gone from chronic insomnia to excellent sleep quality in 3 days using CBT-I.

factualhigh valuespeaker onlynovelty 1/4durability 3/4· Tobi Lütke

by day three except for a night I have [been] sleeping perfectly ever since I mean once a month I maybe like if we walk walk me through this this is like what what are the steps to to do that um I sleep at like I'm going I'm going reading at 10 every evening basically that's sort of like maybe sometimes a little bit earlier depending on how good my book is um and then I'm the go to my bed and I'm sleepy and I I sleep immediately I fall asleep like my sleep Effectiveness rating on my sleep Checkers is basically 95

0.43

The previous model of acquiring all innovation from outside companies (acquire-to-innovate) is fundamentally opposed to Tobi's philosophy; instead, he wants Shopify to innovate everywhere internally because that requires founders to demonstrate that they can solve the full spectrum of problems.

normativehigh valuespeaker onlynovelty 1/4durability 3/4· Tobi Lütke

a sort of an ergonomic for a lot of companies investor in the end state is to become companies that maintain what they've got um and and then acquire all Innovation I I think that's a I mean I would not be proud of [overseeing a company like this] I I I I if if Shopify would turn under my watch into that I think someone else could do my job better um uh like I think companies are like it's Innovation is a Lifeline I think you want to innovate everywhere

0.43

Tying employee lifetime compensation to stock price movements that occur weeks before grant dates—unrelated to company performance or individual contribution—violates basic fairness and creates unnecessary randomness; a employee's compensation should not depend on whether Russia invaded Ukraine the week before their grant date.

normativehigh valuespeaker onlynovelty 1/4durability 3/4· Tobi Lütke

Shopify is the stock price is like this crazy function over time based on again sentiment market value so tying everyone's lifetime earnings really put like to this other thing just like why are they swinging compared to the thing that we are working on feels like just such a pattern violation I think it's just like a steel man wipers stealing me argument but it should affect what uh uh uh you [in a like a Shopify employee uh makes us lifetime earnings whether or not Russia invaded the Ukraine the week before for Grant

0.42

Machine learning progress is accelerating so rapidly that Tobi is having difficulty keeping up with all developments despite paying attention, suggesting that tracking and understanding all progress requires dedicated effort and even well-informed people are losing sight of the pace.

factualhigh valuespeaker onlynovelty 1/4durability 2/4· Tobi Lütke

I can watch three four or five different fields right now or November progressing at Breakneck Pace where I mean especially machine learning is the first time I think I found my [total] capacity like I actually have to say this progresses so fast but I think my model of what's possible is for him right even though I'm trying to make that not true I think sometimes I just don't notice that something is accelerating and far behind but then I can catch up there I'm actually having trouble staying staying uh on top of it

0.20

During the first year of Shopify operations during the pandemic, Tobi worked 14-16 hour days, seven days a week for approximately one and a half to two years, eventually burning out some executives who couldn't sustain that pace.

factualspeaker onlynovelty 0/4durability 3/4· Tobi Lütke

when covet started come in [you can] maybe spot if like spools up chronologically here at the top I the things I shared about um you know going for all roadmap and looking at and canceling a lot of things and doing a million other things besides covet um for me meant 14 16 hour days every day all day like seven days a week uh for probably a year and a half three extra two years probably almost like I think I started taking weekends after a body and a half again um well at least one day um it was just like I I I I lots of my Executives turned over um who ended up just like um that wasn't for them to go into those times