Connector of dots. Maker of lines. Rider of slopes. Kinda sendy, dad. (he/him) 🇨🇦/acc
Toronto, Canada
Joined July 2006
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”Plans are like maps. They animate people. And this is the most crucial thing they do. When people actually do things, they generate outcomes that help them discover what needs to be explained, and what should be done next. “ 2/3
David Crow retweeted
I spent 48 hours in SF hanging out with billionaires, data labs and AI founders and execs running $1B to $100B companies.
My observations:
1. Sooo MANY stories of data brokers making like $2M a WEEK selling company data to labs. I can't tell if it's the beginning or a bubble, and I kept wondering which niches are left. Digging into it actively.
2. At dinner, someone asked the table, "If a new model drops next month, does your company get better or worse?" HALF the table went quiet! I think that's the best question to ask about any AI startup right now.
3. The bar people talk about now is hitting $1B in revenue in 12 months (I guess that's the new unicorn?). What I didn't hear much about is retention. AI revenue can come in fast and leave fast, and I think we're going to see a lot of stories of AI companies with huge revenue and terrible retention.
4. It's pretty clear we're living through the reinvention of the computer. The model is the CPU, the harness is the operating system, and skills and plugins are the apps. Thinking about it that way makes it easier to see where the whitespace is.
5. We're maybe 12 months from an agent that can watch you work for a week and then do your job without any instructions. The screen recording plus agent memory plus local model combination makes this possible right now.
6. Agent harnesses feel like the new GPT wrappers, in a good way, especially vertical ones. The best teams I talked to treat the model as swappable. One founder walked me through routing different models to different jobs: one for taste and visuals, a cheaper one for the everyday stuff, another for text.
They use prompts they can move across models over fine-tuning, and A/B test the output on what users actually do with it: do they edit it, export it, share it? A vertical harness is basically four things: the connectors for that industry's data, evals written by people who know the work, rules for what the agent can and can't touch, and a clean screen for a human to review. The model is maybe 20% of it.
7. There's a lot of reverse engineering going on/cloning going on more than I've ever seen. People are decompiling software and rebuilding it with agents, and someone showed a suite of like 10 apps that are worth $5B+ each all that he cloned open source. Me and everyone are still thinking through what it means when software gets this easy to copy.
8. My guess is the value moves to data. If the software can be rebuilt quickly, what's worth paying for in a legacy SaaS company is the years of customer data and workflows inside it. Some SaaS companies are secretly data companies.
Gets me thinking about how do you truly value data for this saas companies? Like if we were buying these dying saas companies at 2x ARR before (as example), maybe there is a better metric. Idk, just thinking out loud here.
9. It feels like a good chunk of legacy software won't make it to the agentic era, especially anything built around people clicking through a lot of screens.
10. Every company I talked to wants to pipe its internal data into one place and expose it to agents through MCP. Then they look at the data and realize it's a mess: five versions of the same customer, old Slack channels, PDFs nobody can search. Cleaning that up feels like a big consulting opportunity!
11. A lot of founders are building the basic building blocks for agents: APIs, data layers and tools. Some of the companies I saw barely have a UI because the main user is an agent. I really believe the startups that build primitives to this agentic era will do extremely well. Building blocks is the best way to think about it.
12. Labs can get plenty of training data, but it's harder to get real examples of agents failing inside companies. Whoever has those logs has something valuable.
13. Someone running a big consumer company told me the next fight is over memory. The model that remembers the most about you wins, and the smartest model matters less than people think.
14. Physical AI came up a lot. Astra I think was the first model that got people into AI can actually do CAD, and I think a lot of people are thinking what does vibe manufacturing really look like. The line I keep thinking about came from a robotics founder: the hardest problems in AI are deployment problems now, not research problems. Their robots work on their own, call a human when they get stuck, and every one of those calls becomes training data.
15. Cybersecurity companies are having a moment and are actually cool companies to build now, especially the ones that clean up after a breach. Every agent with access to your systems is a new door into your company, and a lot of those doors were left open.
16. Some startups are worth more dead than alive now. A shutdown company with 5 years of Slack, email and code can get paid for licensing all of it. I wouldn't be surprised if founders start factoring that into when they shut down.
17. People are starting to talk about monetizing the agent web. It feels really early, but when the most popular user of the internet is an agent, what startups should you be building?
18. I think agent insurance is coming. Once an agent makes an expensive mistake, insurers will want audits before they cover anyone.
19. Several people said the hire they want most is someone with taste who can write evals. The models are getting good at generating ideas, so the hard part is judging which ones are good.
20. New trend I observed: startup raises VC, uses venture dollars to become a creator, startup fails, founder falls back on being a full-time creator and incubates other products bootstrapped.
21. Getting SIGNIFICANT distribution is HARD right now. Founders are sponsoring buses, buying billboards like crazy and throwing parties with famous DJs to get noticed. Kinda feels dotcom era in that sense.
Attention is what's scarce! The growth guy going viral sharing his UGC strategy from Wispr Flow is a good example. It's the sauce everyone wants, and I truly believe there are probably only 50 people on the planet who know how to scale these types of businesses efficiently in this era.
Always good to get that dose of SF. I felt sooo lucky to have such an incredible trip during such an incredible time in building businesses. Surreal in so many ways.
Happy to be home and locked in.
Until next time!
David Crow retweeted
On Monday, Montreal city council votes on a motion to cut the city's ties with Israel. I am speaking up because this motion is dangerous for Montreal, and my reason has nothing to do with which side of that war you are on.
My family arrived in Montreal in 1956 as refugees. This city gave us safety, dignity and the chance to build. That promise has drawn generations of immigrants here from every corner of the world.
I am not going to debate a war on the other side of the world, and that is exactly the point. A municipal government has no jurisdiction over foreign policy. Cities do not end wars.
But a motion like this lands right here at home. Jewish Montrealers are less than one percent of this city and the number one target of hate crimes. Those are police statistics, not opinions. Our synagogues and schools have been targeted, and families I know are scared in a way I have never seen.
When city hall singles out one community's connection to a foreign conflict, it brings no peace anywhere. It brings fear here.
Montreal has real emergencies. Housing. Homelessness. Infrastructure. That is the job.
This city has been a safe haven for my family and so many others, and it must remain one for everyone. @SorayaMartinezF showed real leadership in June. Council should reject this motion on Monday.
David Crow retweeted
I keep saying, “this one went too far.” At this point it would almost be funny if it weren’t so damn horrifying.
This week, two Jewish owned bakeries (Kiva’s) in Toronto were targeted. Now Noam, where my parents and sister go every week for kosher food, has been destroyed by a fire.
88% of Jewish Canadians feel less safe than five years ago. One in four has considered leaving or made plans to.
These are not random incidents. This is the reality I wrote about months ago.
This is not anxiety. This is evidence.
David Crow retweeted
You don’t have to love Elon Musk to recognize what this headline says about us.
A country that spends more time criticizing wealth creation than encouraging it sends a clear message to builders: your success is tolerated, not celebrated.
Canada should be the best place in the world to build ambitious companies. Headlines like this make us look like we’re not quite ready for that.
The @TTChelps the only transit service on the planet that fails to understand it has one job. Get people to their destinations safely.
4 short turned cars. You owe me a refund.
David Crow retweeted
1/ Today we're announcing Gigascale Capital's $250M first institutional fund to back early-stage founders rebuilding the physical economy.
I have been very lucky to have seen the magic 🪄 @jrodgers creates from StartupCampWaterloo to VeloCity to CDL to Volta to Eigenspace to Builders Club. And all the fun side quests along the way. The magic seems to be believing in people.
Very proud to be your friend.
It feels pretty special to be included on the list of these great Canadians in @BetaKit's 2nd annual Most Ambitious. mostambitious.betakit.com/
I love that @tron made me a floating head... but also included probably the single best bit of feedback from a long standing member.
David Crow retweeted
the pope and anthropic's co-founder just stood together at the vatican to release "magnifica humanitas," the first ever catholic teaching on AI
yes, you read that right. the full ceremony was 2 hours.
here's the most interesting things for you to know:
1. this is the biggest religious response to AI in history. popes only put out a handful of these huge official letters in their entire time as pope. the fact that one of them is about AI tells you how seriously the church is taking what's coming.
2. small detail with massive meaning: this pope picked the name "leo XIV" on purpose. the last pope named leo was leo XIII back in 1891, and his most famous act was writing the church's response to the industrial revolution. picking the same name is a deliberate signal. this pope sees AI as the new industrial revolution.
3. the catholic church does this every time a major technology reshapes humanity. they wrote "rerum novarum" in 1891 to respond to the industrial revolution. when nuclear weapons threatened the world in the 1960s, they wrote "pacem in terris." climate change and runaway tech got "laudato si" in 2015. now AI gets "magnifica humanitas." they don't issue these often.
4. the pope's main line: "AI needs to be disarmed." he literally compared AI to nuclear weapons. he said the church spent decades pushing for nuclear disarmament because the technology was too dangerous to leave in the hands of a few. he says AI is now in that same category.
5. anthropic co-founder christopher olah told the pope, on stage at the vatican, that anthropic's own research team keeps finding things inside their AI models that "mirror joy, satisfaction, fear, grief, and unease."
6. olah's reframe of what AI actually is: these things are grown. they're trained on a structure roughly modeled after the human brain and fed everything humans have ever written. in his own words: "they are made from us, from our words." he said even the people building them don't fully understand what's happening inside.
7. olah publicly admitted that every AI lab, including his own, faces pressure that can conflict with doing the right thing. commercial pressure to keep shipping, competitive pressure from other labs, plus the older pressures of pride and ambition. his solution: we desperately need outside critics with no skin in the game who will tell the labs when they're failing.
8. olah says there are 3 giant questions the AI labs cannot answer alone and the world needs religion and philosophy to step in on:
> how do we make sure poor countries actually benefit from AI?
> what does human flourishing even look like in this new world?
> and what are these things we're actually building?
9. one of the sharpest lines in the whole encyclical: "the promise of automatic general prosperity often proves illusory." translation: the idea that AI will just make everyone rich on its own is a fantasy. someone has to actually design the system so the benefits get shared.
10. the pope also pulled out a 100-year-old quote: "contemporary man has not been trained to use power well." said by a theologian back in the 1920s. the whole encyclical is basically a long argument that we need to learn how to use this kind of power before it uses us.
11. the pope kept stressing that he doesn't have the technical answers. but he says the church has thousands of years of wisdom on what it means to be human, and that wisdom is exactly what's missing from how we're building AI right now. his closing line: this technology should serve "human flourishing and human dignity, not control consciences."
David Crow retweeted
“This is not due to poor domestic compensation; top graduates earn well by Canadian standards. They leave because compensation and upward mobility for their skills are simply higher elsewhere.”
I don’t know who needs to hear this at TD, but compensation is the primary factor behind brain drain.
Yes, high marginal tax rates, tax complexity, etc all matter for our economy. Yes, we need substantive tax reform and simplification. But yeesh.
TD report on CANADA's BRAIN DRAIN is really interesting.
Canada is quietly losing its top talent to the United States in what economists call a silent brain drain. While Canada does a strong job educating highly skilled workers in STEM, engineering, and entrepreneurship, it struggles to keep them due to higher taxes that kick in at much lower income levels, limited opportunities to scale companies, weaker commercialization of ideas, and much better pay and growth potential south of the border.
-> Talent leaves mainly through temporary US work visas rather than permanent moves
-> Outflows are heavily concentrated among the highest skilled, especially in tech and advanced degrees
-> Onward migration is worst among immigrants and top university graduates
-> Canada has a missing middle of medium sized firms, relying instead on many tiny businesses and a few large ones
-> Personal tax rates often exceed 50 percent in major provinces and apply at much lower thresholds than in the US
-> Complex corporate tax rules push entrepreneurs toward tax planning instead of growth
All of this weakens productivity, innovation, and domestic returns on education, making Canada a feeder system for the US economy
REPORT: economics.td.com/ca-silent-b…
David Crow retweeted
CPP underperforms passive indexing. It should have 5 employees, ideally all on vacation most of the time.
My latest, on the continuing fiasco at the CPP investment fund, which has now spent more than $50 billion over twenty years to lose about $100 billion relative to what it might have earned, for an equal amount of risk, if it had just bought the relevant indexes — or flung darts at the stock listings.
theglobeandmail.com/opinion/…
David Crow retweeted
Oh this is just rich... Bill C-22 is driving VPN businesses like ours out of Canada because of the required user logging. And in the same breath you tell people to secure their data with VPNs.
I hope you bought your circus tickets folks, because the clown show is starting.
Public Wi-Fi is convenient, but using an unsecured public network can bring increased risks. Using a VPN protects your data. Learn more: getcybersafe.gc.ca/en/secure…
ALT People using their devices on a Wi-Fi symbol. Text: Public Wi-Fi.
Readers added context they thought people might want to know
VPN providers like NordVPN and Windscribe have warned they may exit Canada if Bill C-22 passes, as it requires electronic service providers to retain user metadata for up to one year and assist law enforcement with access, potentially compromising privacy protections. globalnews.ca/news/11851363/… parl.ca/legisinfo/en/b…
David Crow retweeted
I’d expect a significant exodus of digital technology companies from Canada if C-22 passes.
This bill proposes generalized surveillance infrastructure, not law enforcement.
Incredibly concerning overreach.
It would weaken Canadian cybersecurity, lower the legal threshold for accessing Canadians’ data, and tells both Canadian and global technology companies that Canada is no longer a trusted jurisdiction for building digital infrastructure.
We won't be far behind if C-22 passes. In its current state, VPNs would almost certainly require us to log identifying user data.
Signal isn't headquartered in Canada so they can just shut off Canadian servers, but our HQ is. We pay an ungodly amount of taxes to this corrupt government, and in return they want to destroy the entire essence of our service to basically spy on its own citizens.
Not happening. We'll move HQ and take our taxes elsewhere.
David Crow retweeted
Michael Geist on C-22. Please read
michaelgeist.ca/2026/05/the-…
David Crow retweeted
C-22 is looking like a huge mistake. It worries me a great deal. There is so much nonsense in there that It may well end up dealing a death blow to Canadian tech viability.
We won't be far behind if C-22 passes. In its current state, VPNs would almost certainly require us to log identifying user data.
Signal isn't headquartered in Canada so they can just shut off Canadian servers, but our HQ is. We pay an ungodly amount of taxes to this corrupt government, and in return they want to destroy the entire essence of our service to basically spy on its own citizens.
Not happening. We'll move HQ and take our taxes elsewhere.
“You can hold wonder and grief in the same hand, mourn a version of yourself while sprinting toward a new one.”
Hat tip @aliasaria
David Crow retweeted
Most founders lose VC deals before the first slide. Before they even enter the room.
Here’s the single line from Chamath’s Groq memo that explains why.
The $10M check into Groq’s $25M valuation Series A — an investment that will return billions through the Nvidia deal.
Most people will stare at the returns.
But the most important line in the memo isn’t financial at all:
“Special Person: Yes”
I’ve been on both sides of the table.
As a founder, I pitched hundreds of VCs.
Now I’ve sat in partner-level investment committee meetings, listening to how real decisions actually get made.
And here’s something that surprised me early on:
A shocking number of IC discussions are not about product, models, or decks.
They boil down to one question:
“Is this founder special?”
I used to press investors on this.
What does special mean?
Pattern match? IQ? Grit? Vision?
No one could give a clean answer.
Not because they were hand-waving — but because “special” isn’t a checklist.
It’s a conviction.
It’s that feeling where, after seeing hundreds of founders a quarter, one person creates a pause in the room, an inevitability.
The partner leans back.
The conversation slows down.
Someone says: “I don’t know how big this gets… but this person will figure something out.”
That’s what “Special Person: Yes” really encodes.
At the earliest stages, most deals are 80–90% team.
And that judgment is formed before the spreadsheet is opened, often before the person even enters the room.
Founders should internalize this:
You don’t need to be special at everything.
But you do need to be world-class at something that matters.
Technical depth others can’t touch.
Insight from living the problem for years.
An execution engine that makes normal timelines look slow.
Or scar tissue from doing the impossible once already.
Investors see hundreds of founders a quarter.
They’re subconsciously asking:
Why you?
Why now?
Why should I bet my reputation on this person?
Sometimes the answer becomes a single quiet line in a memo.
“Special Person: Yes.”
And that one line can be worth billions. – at San Francisco, CA
