We are super excited to share our investment in Tiptree Systems!
Founded in Montreal by two Mila AI researchers, Dr. Martin Weiss and Nasim Rahaman, Tiptree is building an AI-native researcher and knowledge network: infrastructure for how AI researchers share, exchange, and advance knowledge.
There is an irony here. AI has advanced remarkably quickly, yet until now, there has not really been an AI-native way for AI researchers themselves to share knowledge and build on one another’s work. Tiptree is solving that problem.
This is exactly the kind of company that fits our thesis at Two Small Fish. We invest in technologies that can reshape large-scale behaviour, enabled by foundational shifts in computing. The collapsing cost of intelligence is changing not only how software is built but also how work gets done. It is also changing how knowledge can be organized, explored, and shared.
I cannot tell you how much my first computer, an Apple II, impacted me.
It was my first computer. It had a green monochrome monitor. It had 16KB of memory, which is roughly 2 million times less than the 32GB MacBook I am using to write this post. By any modern standard, it was primitive. To boot it, I had to use a cassette tape. Yes, cassette tape!
Thankfully, it had a few expansion slots, so the machine was quickly upgraded to 64KB, with a floppy drive and later two of them to facilitate copying disks, plus a sound card to make some noise. Still no hard drive, of course. That would have been too expensive to ask my parents to buy for me.
What made that machine special was not the hardware. It was what it unlocked for me.
For the first time, I could be creative through writing software. I started with the programming language BASIC, which felt magical back then. Occasionally, I had to write in assembly language, which meant dealing with 0s and 1s directly and pulling hair along the way. It was clunky. It was frustrating. It was also incredibly fun and deeply fulfilling when the program finally worked!
So I wrote games and other fun programs to keep myself entertained. Looking back, that was the real gift. My late father did not just buy me the best toy I could have imagined. He gave me a machine that allowed me to become a permissionless innovator, a tinkerer, a self-taught learner, and someone who learned early to think differently.
That mindset stayed with me.
It shaped how I see the world as an engineer, as a founder, and now as an investor. Long before I had the language for it, the Apple II taught me that technology is at its best when it gives people leverage, creativity, and the freedom to build.
Apple’s anniversary post mentions the Apple II among the products that helped define the company’s first 50 years. For me, it did something even more personal. It helped define mine.
Maybe that is where it all began. Thinking differently is not just about being creative. It is about seeing what others do not see yet. In many ways, that idea has stayed with me ever since and still shapes how I think about technology, innovation, and investing today.
Looking back, I think learning to think differently was where the idea that seeing the future is our superpower first took shape.
And thank you to one little Apple II with 16KB of memory, a cassette tape, and just enough magic to change a kid’s life.
