Bram Sugarman
@bram
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Building. Investing. TBD. prev: VP @Shopify, VC @OMERSVentures, SE @EA
Joined April 2008
Bram Sugarman (@bram) is also available for office hours today. He's got a lot of interesting perspectives and investigations happening on the future of startups, what matters and does not matter, we will expand over time and build new systems around this stuff, but chat with him
gonna try this thing, where I'm going to do office hours every friday at New Stadium in Toronto, if you want to go for a walk or chat or you can share what you're working on, and I can share what I'm working on, and thinking about yeah, lmk, this friday can be the first one
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This is completely backwards. **founders** are VC kingmakers. Not the other way around…
VCs deploy ‘kingmaking’ strategy to crown AI winners in their infancy
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gonna try this thing, where I'm going to do office hours every friday at New Stadium in Toronto, if you want to go for a walk or chat or you can share what you're working on, and I can share what I'm working on, and thinking about yeah, lmk, this friday can be the first one
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With all the mega funds & hyperscalers, easy to forget that outlier success starts small. @bendingspoons first acquisition was €10,000, just acquired AOL for ~$1.5B @AltimeterCap started with $3M, now has ~$18B AUM @ThriveCapital first fund was ~$10M, latest fund is ~$8B
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Partnership + Equity 🤝 Greatest form of long-term alignment. This will be huge for both OpenAI and Thrive Holdings. I also love that the Holdings playbook is right here for all to see: "...leading research and applied AI teams working alongside engineers, operators, and
We are excited to announce a strategic partnership between OpenAI and Thrive Holdings. Through our partnership, OpenAI will become an equity owner in Holdings, and collectively we will set out to deliver frontier technology for our customers. For decades, technology has
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Full essay : https://t.co/bZijYQzKfk Also highly recommend the @InvestLikeBest episode:
pod.link
Listen to Josh Kushner - Building Thrive Capital from Invest Like the Best with Patrick O'Shaughnessy wherever you get your podcasts!
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The Inner Ring by C.S. Lewis is one of my favourite essays to go back to. Caught onto it from @patrick_oshag interview with Josh Kushner a few years ago. This paragraph in particular hits hard.
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Last ~6 months I've kept a personal changelog. Notes on what I learn each day. Some days a few short bullets. Others deep technical notes. Some patterns: (1) LLMs best for consensus learning (2) IRL convo best for non-consensus learning (3) Building is my best form of learning
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This. And it always takes longer than you think (hope?).
It’s never as good or as bad as it seems. Keep building!
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I'm rounding up stories about the mismanagement of Canada's $2b in AI compute funding to include in an open letter to government. The money is being funnelled to many unproductive places and being diverted away from our world class AI companies. Pls share your stories!
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Been building an AI product to help small biz owners manage their clients and send proposals/invoices. Have a bunch of happy customers so far If anyone’s down to try, we’re looking for some more feedback, please lmk!
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VCs as kingmaker is complete BS and always fails. If someone tells you it’s true, they have their own agenda. In the end, founders decide which VCs they will make rich, not the other way around
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Non-consensus folks, my DMs are open and we are hiring. In office. Not remote. AI native. Not corpo.
people who make non-consensus decisions to join a company make non-consensus decisions at the company
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If you’ve ever wanted to work with me, LMK. Looking for exceptional designers, operators, vibe coders, marketers and engineers who think long-term. Like or reply to this tweet if that’s you. I'll DM the 10 most interesting ones this week. I'd be honored to work with you
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Equity + Product Partnership creates unique long-term alignment. Love that we’re seeing more of this across founder-led companies 🤝📈
Snapchat + @perplexity_ai 🤝 Starting in early 2026, you’ll be able to ask questions, explore new ideas, and get credible answers right inside chat. AI that feels more personal, social, and fun! https://t.co/5J10blvzhR
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Same goes for M&A.
It only take 1 VC to get a deal done, it only takes 2 to get a good price.
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This is basically the city of Toronto announcing “The Purge has begun”
Reminder: we know the game is running late, but transit won't wait! The final GO train leaves Union Station soon, and the last TTC train is around 1:30 a.m. Check schedules at https://t.co/usz3GwL3Ih and
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Going to be way before H2 2026. Q4 2025 or Q1 2026.
Sources: OpenAI is preparing for an IPO that could value it at ~$1T and has looked at raising $60B+, filing as soon as H2 2026 and listing in 2027 (Reuters) https://t.co/T7kku1sszH
https://t.co/shx6Q03cCm 📫 Subscribe:
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