* 100% open source models: Why 100% open source everything? What's the real goal, and what's a slogan? Even Mozilla hides a lot. Open what you can and what is really important to you, and if you really want it to be everything, you can do that on a defensible delay. (We're starting with our non-differentiating framework layers, and now that we're starting on our next layer of differentiating tech, are considering how to open the previously differentiating stuff.) If the choice is slow open growth vs massive partially-open growth, the total amount of open source is actually SMALLER in the 100% open approach. Likewise, if the choice is death over partial open source, not dying means you can do more open work.
* Use of venture capital: The risk of going on the treadmill of always needing the next round is real -- we went slooow on spending ours to avoid that. It's not inherently a bad idea though: companies have successfully bought their way into success. Pay enough great execs for enough time, and cheapen the cost of product enough to avoid competition, and something real will pop out. HOWEVER, a conservative way to think about it is (A) there is a step function to getting to a real worthwhile & sustainable product, which requires capital (sweat, time, VC, whatever.) And (B) after you get there, and revenue growth gets predictable, it's worth increasing spending more this year to have bigger revenue next year. If you bet wrong, you simply slow hiring and wait for natural revenue growth to catch up (it's math!). This is hard, and if you fail at (A), that means layoffs while you try again. It's not necessarily death -- RethinkDB called it quits instead of going to a skeleton team.
* Risk: For the same reason as above, I actually view not reaching the point of a sustainable product as risky in the short-term, and not reaching a maintainable competitive position risky in the long term (esp. in tech, where the world changes every 2-3 years!) It's worth considering why, if you fail getting to point (A) above with VC, how you'd have succeeded without VC. (Taking VC != going all out on a single marketing & sales blitz)
With that view, what Github and Jupyter are doing is (arguably!) leading to better and more sustainable software than Sage's approach, and leading to more open source code than Sage.
(And more a throwaway: A VC is a buyer of a chunk of your company and needs to turn it into a different sized chunk based on the size of their fund. If they're a big VC, they will only buy it if they see it turning into a $1B+ return. Your job as a company builder is to know what revenue you can get & when; it's weird to approach it as some sort of laissez faire random walk. Likewise, as a salesman to a VC, your job is to show you're selling what they need to buy. Not being aware of what the customer wants is a bad start. Doing my best to understand this stuff is part of my obligations to my team.)