
Building. Investing. TBD. prev: VP @Shopify, VC @OMERSVentures, SE @EA
Joined April 2008
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This really blew up. Which is awesome. I'm not a student so figured I'd shed some light on why I care: I love poker, I believe Canadian students are top-notch, and this competition is really fun.
🧵👇
@abhishekm1636 did a really good job building and designing the system (from what I can tell?). The traces and observability are a nice touch. i I hope lots of Canadian students will join. And that 1 or 2 of them will win. Lets go 🇨🇦🇨🇦🇨🇦!!!
Bonus: my prediction is that @abhishekm1636 will spin this out into a company focused on agent betting. With the rise of Polymarket, Kalshi, Fomo and others, this feels like the next evolution.
Abhishek - I'd love to invest when you do 🙂
If I was at a growth stage fund, Sierra is the single company I'd be working hardest to invest in.
@btaylor & @claybavor are obviously generational founders. Add the greatest technology acceleration in history, an inspired team & focused execution. Enormous value being built.
Oh...and Canadian Tuxedos.
Every quarter at Sierra, we celebrate the end of the quarter with Double Denim Day (or, as some like to call it, Canadian Tuxedo Day) 👖. This Q3, we needed a lot of denim to celebrate the most remarkable quarter in Sierra's 2.5 year history.
We added over $150M ARR this quarter, bringing our total ARR beyond $400M. Remarkably, we added more ARR in one quarter than we had all of last year.
The most exciting thing to me is that our pace is accelerating. It took us six months to double from $100M to $200M ARR, and only five months to double from $200M to $400M ARR.
@claybavor and I are grateful to our customers and proud of the entire Sierra team.
If I had negotiated this @cohere deal for the government, I'd have done:
- no cash investment
- warrants and/or options
- commercial deal for government using cohere products
- distribution deal for government suppliers, vendors & partners
- abundant compute supply
No clear details (yet), but it looks like some version of these may be included. Words like "equity", "up to", and "...commercial investment" are telling.
Although press framing is different, my read is that the government is stepping up as a landmark customer for Cohere bringing revenue and users. Cohere can build big on that foundation.
Canada’s sovereignty depends on our ability to build, adopt, and govern AI on our own terms.
That’s why Canada is taking an equity stake in Cohere — one of the world’s leading builders of secure AI.
Sovereign AI. Built here at home.
Read more: pm.gc.ca/en/news/news-releas…
Refreshing reminder that world class technology, world class products and world class companies can be built anywhere. @Sirupsen & @turbopuffer are playing a different game from Ottawa, Canada. Great piece.
The people of Silicon Valley are unwell.
If you work at a frontier lab or decacorn, you’ve got it bad. You haven’t seen your kids, your girlfriend’s annoyed, invites from friends to hang out are waning, even weddings are on hold. This is the time to make your mark and make your money, after all.
If you’re building a startup that’s trying to compete with or be one of these companies, you’ve got it bad. Maybe you passed up a job offer at one a couple years back, which means you left $100M on the table, you fucking idiot. Being an underdog isn't as fun as you thought.
If you’re working on a pre-AI startup, you’ve got it bad. Not too long ago you were the belle of the ball, but now your 30% year-on-year growth doesn’t feel like growth at all. It feels like death.
"Too many of my friends are spiraling," Brie Wolfson writes. "I don’t know how we’re supposed to live and work like this."
It’s all too much, too fast. Too much money, too much growth, too much power, too much change. Every month, a new frontier model is released. Every day, a new unicorn is minted. Seriously. 300 days into the year 2026, and 311 unicorns have been minted so far.
So what’s left for the sane ones? Brie went looking for teams playing a different game. She found one in Ottawa: a search infrastructure company that many of the AI darlings rely on.
It's growing fast, and its people are well.
Read @zebriez’s latest company dispatch from inside the sane asylum of turbopuffer.
colossus.com/article/sane-as…
This is awesome. Assume it’s only U.S. Universities because @UAlberta CPRG would dominate? @Alfred_Lin @sequoia can you open this up to Canadian Universities??? The poker talent here is 🔥🔥🔥
Announcing No Limit: a bot building tournament hosted by @Sequoia, @citsecurities and @OpenAI.
Teams of 1 or 2 get 60 minutes to build a pokerbot from scratch.
Agents play thousands of games across six scored rounds.
Open to university students and recent grads (‘25 or ‘26).
Regionals in Boston, Pittsburgh and the Bay Area in early November. Top five teams from each fly to the Finals. $100K grand prize.
The next wave of great founders and companies will use AI as an abundance resource focused in two areas: science and creativity.
Gaming is an obvious example. Some of the best technical and creative minds already build games. Can't wait to see what they unleash.
Last week to apply for Catalyst 003: Critical Minerals 🇨🇦
Looking at the applicants now, I'm SO SO EXCITED to kick this Catalyst off, bringing together a bunch of experienced geoscientists and software people that want to learn and contribute.
🇨🇦🇨🇦Catalyst 003: Critical Minerals 🇨🇦🇨🇦
A month long working group to explore, understand and make progress on problems involving the processing of critical minerals in Canada.
Apply at: catalyst.ambition.inc/critic…
Bram Sugarman retweeted
Every now dreams every night - processing the day's client and operating activities - to prioritize the top 5 things your biz should focus on next.
We're A/B/C/D testing Argon/Astra/Fable/Wonder to see which delivers the most prescient priorities.
New this week:
1. Priorities - every morning Every picks your top five things to do across your business and puts them at the top of your Inbox
2. Whose turn it is - every open deal now shows Your turn, Their turn or No contact
check it out 👉
every.ai
Bram Sugarman retweeted
I’m looking for 6 Toronto families to try Torch, the instrument we’re building to make playing and singing easier.
Beginners or lapsed players. Borrow one for Nov; help us learn what makes you keep playing—or stop.
Email me: [email protected]
Bram Sugarman 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!






















