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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.
She would know
#REPORT: Former Deputy Mayor Under Olivia Chow, Now Liberal MP Jennifer McKelvie, Endorses Brad Bradford For Mayor. ✅
“He Is the Mayor That Toronto Needs.”
tobi lutke retweeted
Former deputy mayor under Olivia Chow endorses Brad Bradford torontosun.com/news/local-ne…
tobi lutke retweeted
A vote for Olivia Chow is a vote for:
Wasted tax dollars
Large tax hikes
Dysfunctional TTC
Dangerous drug ridden streets
And totally ignored outer wards
Liar and a cheat:
tobi lutke retweeted
“Please, vote for Brad Bradford.”
-Jennifer McKelvie, former deputy mayor.
WOW! That's quite an endorsement.
Brad Bradford is a rare politician who has support from both Conservatives and Liberals.
He's clearly the leader Toronto needs right now.
torontosun.com/news/local-ne…
tobi lutke retweeted
Canada can replace two terrible, destructive, ideologically-driven progressive leaders in a 3 day span. Let’s do our part Toronto.
tobi lutke retweeted
Breaking: Canadians pay too much income tax. 🙄
Anyone with a paycheque could've told you that for free.
New international tax index: Canada ranks 28th of 38 countries on personal income taxes.
34th on capital gains and dividends. 📉
Ontario's top rate hits 53.5%.
It kicks in at 2.8x the average wage. In the U.S.? 8.7x.
Carney's big fix was one point off the bottom bracket.
Then Ottawa scratches its head over why talent keeps heading south. 🤦🏻♂️
Basic math, eh? 🇨🇦
tobi lutke retweeted
Lefties: “Elon Musk should be in prison!”
Normies: “For what?”
Lefties: “We’re not sure but we’ll find something! Vote for us and we’ll show you.”
Normies: “You are insane.”
Lefties: “Elon is a fascist. We’re anti-fascist. You must also be a fascist.”
Vote Brad
Wow, when the "progressive" paper, the Toronto Star, can't endorse the "progressive" candidate, Olivia Chow...
It's really telling.
thestar.com/opinion/editoria…
tobi lutke retweeted
Wow, when the "progressive" paper, the Toronto Star, can't endorse the "progressive" candidate, Olivia Chow...
It's really telling.
thestar.com/opinion/editoria…
Canadians Are Running Out Of Time To Oppose The Dangerous C-22 Surveillance Bill
eff.org/deeplinks/2026/10/ca…
tobi lutke retweeted
I accidentally built a consumer app that 50k+ people this week spent 30 avg minutes using. GA4 says that's in the top %0.00001 of apps.
I've always wanted to visualize wind + waves together, turns out that's hard. Also wanted to build the weather app that I'd use daily.
My CUDA skills suck... but software can just be wished into existance now. Here's a swell shader and a three.js wave model trained using 1k+ ocean images across different conditions, cross-checked against storm literature. Full wx ingest pipeline, tiling service, our own basemaps. Our team did a great job marketing it as well... so that helped! Costs cents to run. Too much fun.
freethewind.com
tobi lutke retweeted
Global News should note much more prominently that this poll was commissioned by CUPE Local 416 (Toronto Civic Employees’ Union), who have formally endorsed Chow as their preferred candidate
Toronto election: Chow holding decisive lead over Bradford, new poll indicates
globalnews.ca/news/12118421/…
… vote Brad!
New 30 km/h area speed limit signs will be posted at neighbourhood entry and exit points. Once you enter a signed area, the 30 km/h speed limit applies throughout the local road network until you leave that area.
Slower speeds help reduce the risk of serious collisions and make neighbourhood streets safer.
Learn more about the change: toronto.ca/LocalSpeed
Incredible work
the beauty of the new @vercel & @Shopify partnership, you can add some whimsy back to the web.
KidSuper x DC Super-Villans Out Now!
DCSV.KIDSUPER.COM
Excellent code mode env:
github.com/stencil-hq/dquick…
MCP vs CLI for LLMs is the wrong discussion. People are debating at the wrong layer.
Both work incredibly well as long as they are run through a repl like environment that can persist state. The funny thing about CLI is that CLI tools are usually accessed through BASH which happens to be a repl with persistent state (the file system), therefore cli works much better than mcp. But this isn't even close to being an intrinsic property of MCP. Just means that we need better harnesses.
Right now the best repl for this are:
- bash + fs
- jupyter kernels
- codemode type repls, usually quickjs
LLMs understand the concept of forward evolving a system to solve a need very well. This comes from the agentic RL. They understand how to change the state of a codebase or acquire data from databases and then operate on it similarly to humans. But without an execution environment, they actually cannot do this properly.
My bet? Sometime soon someone will (or has already?) create a embeddable, sqlite style mini execution environment that parses bash, typescript, or tool calls into a common IL execution plan that's easy to security check before executing. And design this specifically for durable execution environments. Then we will just connect cli, mcp, webmcp, whatever to that and it accepts any of the input modalities as they can all be represented as each other.
tobi lutke retweeted
Chow getting absolutely cooked in this @CP24 debate.
Defends a housing record that hit 2% of her own target. Defends the biggest tax hikes in a generation.
Fail on safety
Bradford is landing every punch.
Toronto is watching. It’s not pretty.
#TorontoElection #TOpoli #ChowFail































