Pinned Tweet
Yea that was a fun one.
Thank you for celebrating the glory of entrepreneurship, David.
My conversation with Tobi Lütke (@tobi), co-founder and CEO of Shopify.
0:00 Companies as Social Technology
5:27 The Value of Reading Books: Cheat Codes for Life
7:28 Post-IPO Crisis: Cosplaying as a CEO
7:54 Competition vs Rivalry: The Power of Healthy Competition
16:02 COVID as a Turning Point: Rebuilding the Executive Team
18:21 Hiring Founders: Building a Team of High-Agency People
26:49 Shopify OS: Engineering the Company from First Principles
36:48 Compensation Innovation: Giving Employees Full Agency
40:41 The Psychology of Identity and Affirmations
48:43 Differentiation Over Perfection: Making It Your Own
50:31 Context Podcast: Documenting Decision-Making
1:26:36 The IPO Decision: Going Against Silicon Valley Orthodoxy
1:35:08 Building a Company Worth Working For
1:41:50 Hiring for Spikiness: Finding Non-Conformists
1:48:28 Office Design Philosophy: Creating Space for Excellence
1:58:54 Video Games as Business Training: StarCraft Lessons
2:07:06 AI Revolution: 2026 and Beyond
2:11:44 Focus on Craft: The Unquantifiable Elements of Excellence
2:21:08 Survivorship Bias: The Importance of Entrepreneurial Exposure
2:23:22 Closing
Includes paid partnerships.
tobi lutke retweeted
How has global poverty changed in our lifetimes?
No matter what poverty line you choose, the share below it has declined globally.
tobi lutke retweeted
Brad Bradford started 17 points behind Chow and has passed her in the final stretch of the race with a narrow 2 point lead.
I expect that gap to grow this week. Toronto is ready for change.
#Vote4Brad
cbc.ca/news/canada/toronto/t…
tobi lutke retweeted
Five days to go. Toronto, the choice is yours.
If you want to change the city, you have to change the mayor.
Vote for change on October 26.
tobi lutke retweeted
A lot of buzz about this @markrmcqueen piece in today’s @TorontoStar. It is our most-read column this morning.
thestar.com/opinion/star-col…
tobi lutke retweeted
Replying to @truckdriverpleb
Completely out of touch with her voting base.
A. B. C.
Anyone
But
Chow
Day one for Claude Duet and Shopify already connects
Design a store right in the chat, then use Duet to stay on top of performance
Of course it’s net negative
this California wealth tax thing is just incredible.
so in October 2025, a California healthcare union proposed a "one time" 5% tax on any billionaire's wealth. the ballot measure will be voted on next month. In early December 2025, California announced that it would be a retroactive tax if passed, applying to anyone with CA residency as of Jan 1, 2026. The objective is to pay for Medi-Cal, California's incredibly dysfunctional healthcare system. (which also functions as a glorified welfare apparatus, but that's a discussion for another time).
polls reveal that the CA electorate is split around 50/50 on the tax, but prediction markets only give Prop 40 a ~23% chance of passing (there are competing measures on the ballet that would nullify it).
there are 200 billionaires in CA, worth collectively somewhere between $2.3 and $2.6 trillion. 5% of that is around $100b, accounting for a small amount of attrition. proponents of the tax forecasted a significant windfall, assuming only a 10% departure rate.
supporters thought they were being clever with the retroactive concept. no billionares would leave CA in the few short months between the tax being proposed and the residency cutoff date, without the tax even having passed yet, right?
well as it turns out, they did.
a new paper [1] from two academics at Stanford called "The Net Present Value of the California Billionaire Tax Act", argues that not only did more billionaires leave due to the proposed tax than its proponents expected, but that the value of the tax, if it does pass, is actually negative.
proponents of the tax only assumed 10% avoidance, that is, only 10% of the taxable base of targeted billionaires would leave CA within the very short Oct-Dec 2025 window. Jaros and Rauh, the Stanford academics, find that a lower bound of 28.6% of the taxable base managed to leave.
just based on known departures, those departures total $577b in net worth, or $28.8b in potential tax lost. this of course does not capture everyone (many left without announcing their departure), so the authors normalize to departure rates estimated from other wealth tax events, and apply other discounts for litigation, arriving arrive at a figure of only $28-$36b in forecasted tax revenues.
but this isn't all! all of the income taxes paid by the departed billionaires are also forsaken. the authors estimate that CA billionaires pay $3.3- 5.8b in annual income taxes. they assume a midpoint of $2b lost in annual collections from departed billionaires. the net present value of that lost income stream is -$68.9 billion.
so when you add it all up you get:
+ $30b one-time tax windfall (estimated)
- $69b in present value of lost future income taxes
= - 38.9b overall net present value of the tax
of course, this analysis is highly estimate driven. the authors simulate the parameters 100k times and find a negative NPV of the implemented tax 85 percent of the time.
and if the tax doesn't pass, which it's not looking like it will, California still ended up losing at least $577b in departed net worth, and they have permanently poisoned the well with entrepreneurs who will now worry about future wealth taxes.
[1]: nber.org/system/files/workin…
tobi lutke retweeted
Tobi reposted our warehouse.
So we had Claude Opus 5.5 follow one Shopify order from the click to the door.
tobi lutke retweeted
Today marks 1 year of joining Shopify. The shift from startups to a large public company has been a thrilling learning adventure, but exciting as hell.
- Things move slow
- Bureaucratic process everywhere
- Decisions take forever
That's what I was warned it would be like. But here's how it actually is:
- Things move as fast as how great something can be
- Process is constantly questioned and trimmed
- Decisions are simply a DM away
Big things are happening and I'm excited about what's to come. This morning I joined @ridd_design for another dive club episode to talk about my experience in all this, and I'm so stoked to share our chat when it comes out in a few weeks.
Happy 1 year, Shopify. Thanks for having me around.
tobi lutke retweeted
Brad Bradford is going to be the next mayor of Toronto. torontosun.com/opinion/colum…
Vote Brad
Six days before Toronto votes, our new Build Canada survey shows:
60% of Torontonians want a major change in direction at City Hall
67% would rather City Hall try new ideas, even if some fail
61 % of long-term residents say Toronto is a worse place to live than four years ago
54 % have seriously considered moving out of Toronto in the past 12 months, rising to 63 percent among 45- to 54-year-olds
tobi lutke retweeted
Clairic: a new System One class of extraction models
a brand new model paradigm! introducing 𝚌𝚕𝚊𝚒𝚛𝚒𝚌: a system one model for extracting, computing, estimating, and predicting values from unstructured inputs.
blog.cloudflare.com/clairic-…
This is extremely well crafted. You have to try it out
Wabi 2.0 is live!
personal agents are one person, one chat. but the parts of life that matter run on more than one person
Wabi is an agent you use together. you talk to it, it does stuff, builds the apps you need, and anyone can join the thread - your partner, your best friend, the preschool moms groupchat
school changes pickup time → Wabi updates the family calendar, everyone sees it.
a show you’d both love → Wabi finds a night that works, gets the tickets.
the trip everyone keeps talking about → Wabi picks the dates, builds the itinerary, books it
go start a thread with your people 👇
tobi lutke retweeted
Most warehouse managers never see the whole floor at once. So Claude Opus 5.5 built them the view from above.
93 people, 320 robots and every truck on Black Friday, live.
tobi lutke retweeted
On my way to the office this morning, I passed a group of young people protesting, a Palestinian flag draped over their shoulders.
And I asked myself a question I can't shake: why does this generation always fall into the same trap? No matter the history. No matter the context. Even the ones from wealthy families, who went to the best schools, who were dealt every good card. Always the same trap.
I don't think it's stupidity. I think it's a mechanism. And a mechanism can be taken apart, piece by piece.
A. The observation: everything the state touches becomes unaffordable.
Look at economist Mark Perry's famous chart, the one people call "the chart of the century." It tracks US prices since 2000.
At the top, what explodes: hospital services, college tuition, textbooks, childcare, housing. Increases of +100%, +150%, up to +250%, far above general inflation.
At the bottom, what collapses: TVs, software, phones, toys, clothing. A TV today costs a fraction of what it did in 2000, for an infinitely better product.
Look at what separates the two groups. It isn't technology. It isn't complexity. It's one variable: how much the state is involved.
At the top, sectors that are subsidized, regulated, shielded from competition, where the state funds demand and blocks supply. At the bottom, sectors where companies fight every single morning to serve you better and cheaper.
B. The mechanism: why it's systematic.
When the state subsidizes demand without freeing supply, prices rise. Every time. Guaranteed student loans, and universities raise tuition. Housing aid plus blocked building permits, and rents skyrocket. Administered healthcare, and bureaucracy eats the budget before it ever reaches the patient.
In France it's even more vicious, because the price doesn't disappear: it hides. You never see the hospital bill, you pay it through payroll contributions. You never see the cost of school, you pay it through taxes. Public spending at 57% of GDP, one of the heaviest tax burdens in the world, more than €3.4 trillion in debt. And the result? Overflowing ERs, falling PISA scores, young people who can't afford to live in the city where they work.
The market didn't fail in these sectors. It was never allowed in.
C. Suffering demands a culprit.
A 22-year-old lives all of this in their bones. They can't find a place to live. Their degree either buries them in debt or opens no doors. The future feels blocked. That suffering is real, and I don't deny it for a second.
But human beings can't stand suffering without a culprit. They need a face. A scapegoat.
And this is where everything is decided: who taught them how to read the world?
D. Whoever tells the story picks the villain.
Schools are public. Universities are public. Culture runs on grants. Film goes through funding committees. Public broadcasting shapes the narratives. The people handing down the interpretive framework are, overwhelmingly, paid by the very system that creates the problem.
Do you really think that system is going to name itself as the culprit?
No. It names the capitalist. The boss. The landlord. "The rich." The multinational. The commercial West. Same role, same casting, every time.
E. One lens, a thousand causes.
And this brings me back to that flag. A generation taught to read every situation through a single lens, oppressor on one side, rich, Western, capitalist, oppressed on the other, will apply that lens everywhere. To housing. To climate. To conflicts on the other side of the world. The cause changes, the lens stays. That's why the trap is always the same: it's not the cause that draws them in, it's the way of thinking that was installed in them.
F. The perfect inversion.
Here's the irony. Capitalism is the force that drove down the price of almost everything it touched. The state is the force that blew up the price of almost everything it captured. And young people blame the first for the crimes of the second.
It's like blaming the firefighter for the fire because you saw him at the scene.
G. The ballot box confirms it.
In the US, a few weeks out from the midterms, a large share of urban young voters is getting ready to vote Democrat for more state, more spending, more regulation. New York elected a self-described socialist mayor, carried by young voters, on promises of rent freezes and city-run grocery stores. Rent freezes, the policy that has made housing scarcer everywhere it's been tried. The cure that worsens the disease.
In France, it's the same play in two acts. Part of the youth votes for the radical left, which promises more state. Another part votes for the center, which promises to "manage" the state well, and has dug the debt deeper than ever. Two different ballots, one shared assumption: the problem is the market, the solution is the state.
H. The way out.
These young people aren't stupid. They're right to be angry. They're just aiming at the wrong target.
The day they understand that their rent, their tuition and their hospital are expensive precisely because the state runs them, their anger will change direction. They'll stop protesting against those who create. They'll start protesting against those who capture.
That day, the greatest intellectual scam of our time will be over.
































