Bram Sugarman

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.

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…

UPDATE: We are able to expand eligibility for No Limit to university students in the U.S. and Canada. (Plus recent grads from ’25 or ’26.) Apply to the closest regional event. Registration now open.

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…

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 games we've long wanted, which didn't exist because they'd cost several times more to make than they'd earn back, will soon become possible. As will the games developers wanted to build, but couldn't with the resources available. It'll be a new golden age of gaming.

Canada's AI advantage starts with our people. Today, we announced up to $162 million through Mitacs AI Advantage to create 10,000 paid AI-related work placements for young Canadians. At a time when countries around the world are competing for talent, investment and growth, we're investing in the next generation of Canadian innovators. More opportunity. More skills. More Canadians building the future. That's how we keep building Canada strong. 🇨🇦 L'avantage du Canada en IA, c’est son talent. Aujourd'hui, nous avons annoncé jusqu'à 162 millions de dollars pour L'avantage IA de Mitacs, qui créera 10 000 placements professionnels en IA pour les jeunes Canadiennes et Canadiens. Alors que les pays du monde entier se font concurrence pour attirer les talents, les investissements et la croissance, nous misons sur la relève canadienne en innovation. Plus d’opportunités. Plus de compétences. Plus de Canadiennes et de Canadiens qui bâtissent l'avenir. C'est comme ça qu'on continue de bâtir un Canada fort.

One of the most important things to know about this AI cycle is that no one knows what they're talking and even very smart and plugged in people are continually reversing their opinions and then re-reversing them three months later.

Here's Stripe's letter to investors explaining its acquisition of OpenRouter (LEAKED)

If you want to sell your company, it's far easier when the acquirer is already a customer and sees how critical you are to them. As they say: companies are bought, not sold. Make it known first hand that you are indispensible.

Yesterday, my OpenAI collaborator and I gave a detailed talk on the Huggingface incident, our models creating "the message board", model misalignment, and more. youtube.com/watch?v=87DyyMV0… I hope it can answer a lot of the questions folks have, and we will release a full detailed postmortem at a later time!

Credit to @bendingspoons for having the 🏀 🏀 to pull off these deals when no one else will This rundown is a bit blind to actual structure, but a fine place to start I’m guessing there would be interest for those last-stage investors, but as @bgurley pointed out, a lot of late-stage SaaS was done as straight money — chasing a lot of challenging dynamics on the board level Here we are 5 years past peak SaaS, and we are finally sorting out these deals — which is a good sign Congrats to @airtable on a fantastic product and run… shocked Google, MSFT, and other major players didn’t jump on here There’s so much SaaS to buy right now, but I guess it’s too small compared to AI for folks to find an internal champion I would love to fund a roll-up vehicle of the smaller SaaS startups; < $100m in revenue

Steve Jobs emails Palm's CEO August 26, 2007

M&A is going nuts right now for AI startups. It's Monday at 10:58am and 2 people have already emailed me trying to buy my company, unsolicited. The X timeline is saying the "death of software" and RIP good times, I think there are TONS of buyers to scoop up AI native startups (with EBITDA). Some data: 1. Startups buying other startups jumped 18% in the first half of last year, driven almost entirely by a 30%+ surge in early-stage deals. 2. Private equity is sitting on over $2 trillion in dry powder and competing so hard they're paying about 3 turns of EBITDA more than strategic buyers just to win deals. 3. The market flipped to rewarding profit over growth: in 2021 growth mattered 2.5x more than profitability, and in 2026 a profitable business growing 25% beats one growing 50% while burning cash. This is one of the best times to build there has ever been. Cheap tools, hungry buyers, and insane opportunity to build the AI-native version of things. Anecdotally, based on a lot of people I know, there's a ton of M&A for startups that aren't reliant on Google SEO and built something truly AI-native in hardware, mobile apps, or vertical AI agents. Tune out the doom. Build something worth buying. Keep going.

toronto startup culture invented a type of networking where everyone’s connected but nobody actually helps each other