A similar number of visa types over similar number of years and I would go a step further and say that there is no formal solution to your problem. The US immigration system can't handle YC type rhythm and structures.
You'll have to assume you have two operations to run - your startup and your status. You'll have to get knowledgeable and creative in both. Also, as you will work under the assumption that your start-up may fail, you should also work under the assumption that your status will fail and you will have to go back to your home country. Succeeding in both operations is possible, but very hard. Me think the immigration operation is harder....
Good luck.