David Crow

”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

“You can hold wonder and grief in the same hand, mourn a version of yourself while sprinting toward a new one.” Hat tip @aliasaria

Hey @WestJet you misspelled it. It’s WorstJet

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.

Oh Stripe Atlas equivalent for 🇨🇦

"Yours to Discover" by internetVin My little talk at Toronto Tech Week 2025. This was a new format and setting for me, I was pretty nervous about it, but I thought I would just try it out and see what I would learn. Thank you for everything so far.

@byosko Companies are inherently risky. But it is the illiquidity that will ruin your returns (and DPI).

Just signed dissolution papers for a startup I invested in many years ago. At one point the startup was worth $500M or so, and I thought, "Damn, I'm a genius at this investing thing!" 😂 Startup's value in the end: $0. At least I got $0. Not sure about the founder(s) and early investors. But it was a firesale. The founder, unfortunately, brags a great deal about how much money he raised, how successful he was, etc. And people follow him, love his content, believe he's a guru. I'm not suggesting he doesn't have lessons to share, but I've never seen him admit to failure, only hyping the "success" of fundraising (from top tier investors), and the amazing company he built. To be clear: Failure is part of the process. Startups are high risk. I don't begrudge the founder for trying. I understand the risk of investing. But the lack of self-awareness, humility and honesty with everyone else (who then blindly follows) is sad. Of course, this isn't the only case of this sort of thing--happens a lot.

From superclusters to battery plants - this government has wasted billions.

Happy Belated Mother's Day. I've decided we are rebranding Father's Day. Henceforth, it shall be known as "Mother Fucker's Day"

1/ The hiring/job market in tech is broken an no one is talking about it. It's insane.

@classonde 🎯

Fintech is constantly misunderstood IMO. It's not just payments, lending, crypto or neobanks. It’s fraud detection, compliance infrastructure, embedded products (like insurance), alternative underwriting, capital market solutions, and so much more, including brand new financial products never offered previously. If you're only looking at the app layer, you're actually missing the biggest opportunities.

@AdamAllAccess @bram Question should be: Sun Valley or CMH?

@bram 50% hit rate ain’t bad… we talking A list or B list? Sugarloaf or Snow Valley?

2 founders I spoke to this week, being courted by mega funds (dinners, ski trip invites, celebrity intros...): Founder 1 (enamoured): This is amazing. Can't wait to work with them Founder 2 (confused): Is this how they spend mgmt fees? I just want to be heads down building

The Canadians stay in the USA and raise more money The ones that stay in SF after demo day become unicorns at 2.5X the rate I had a pod dinner tonight and our whole row of founders I sat in turned out to be Canadians who are all going to base their startups in SF after demo day

“Products are made in a factory, but brands are created in the mind.“ - Walter Landor

Shopify killed the Toronto tech scene. Here's my working theory: between 2013 and 2020, Shopify's hyper growth created a talent vortex. It wasn't just engineers – they strategically acquired and aggressively hired Toronto's entrepreneurial energy into one massive ecosystem out of 80 Spadina Ave. The builders, designers, and founders who normally would've started their own companies were all drawn into Shopify's orbit. But it wasn't a death sentence more of an incubation period. Inside Shopify, these builders weren't just pushing pixels. They were operating like "startups within a startup," helping scale one of Canada's biggest tech successes from IPO to $100B+. This pressure cooked a new generation of Canadian operators who mastered both startup agility and big-tech scale. Post-COVID, we're seeing a renaissance in Toronto tech. Shopify alumni are now launching community experiments and new companies – from New Systems @internetvin, to Studio 535 by @fahdananta and I, to @skanwar acquiring Betakit, to policy initiatives like Build Canada with folks like @ddebow - to name a few. We aren't just building companies...we're building our ecosystem. Sometimes a tech scene needs to concentrate before it can multiply and accelerate. And if you ask me, this is the best time to be building here!

Presidents Obama and Bush on their way to the Capitol Rotunda: Staffer to Bush: “Are you going to behave?” Obama chimes in from behind: “Nope.”

“Change your opinions, keep to your principles; change your leaves, keep intact your roots.” – Victor Hugo

VCs to avoid (with a “fuck off”) If some are innocent, they should come out and out the culprit. Pic by @EricNewcomer

Canada’s culture has become a toxic mix of insecure impostor syndrome and a hatred of non conformists. The result is a social and political culture that doesn’t take advantage of its natural resources (including its human capital) and, instead, apes stupid ideas (particularly from Europe) that make it seem like it’s a progressive utopia - like it did with climate change, wokeism and dei grandstanding for the past decade which then drove its economy into a ditch. Separately, the aping of stupid ideas creates resentment amongst its people which they then take out on outliers and anyone that questions the status quo. This is why entrepreneurial people don’t really exist in Canada. They have overwhelmingly found a more hospitable environment in the US and so left. Doesn’t mean there aren’t a few examples of it happening but there are many more Canadians who have made or helped make huge companies in the US vs Canada because of the intersection of these terrible political and social traits.

If Pro Wrestling and Religion are Fake, Explain THIS?!…

Many of crypto's best started their journeys in Canada, including Vitalik. But our government and banks keep crushing the industry through over-regulation. Why does innovation always flee this country? Love to see Canadians like Brian being more assertive.