1) As mentioned by another comment, B2B customers may care about the size of your team if you are doing something business critical. From their perspective, th

1) As mentioned by another comment, B2B customers may care about the size of your team if you are doing something business critical. From their perspective, they don't want to depend on a product that may not be there if one guy gets sick, takes a vacation, flakes, etc. One approach I have seen some people take is to answer something like "the team is under 10 people" which is technically true (ish) 2) A startup is about risk management. At the beginning, there are ALL the risks (can you build it, are you building something people want, can you find those people in a scalable and economically efficient way, will those people pay enough for the product, etc?). Your goal as a founder is to quantify and reduce those risks in a methodical way. Your milestones should be tied to that goal. For instance, to address the first risk listed, you can set a milestone for developing a prototype. For the second, you can set a milestone for getting the first live customer, and so on and so on. My suggestion is to prioritize risk and set your milestones to address the biggest first (hint: it almost always is figuring out whether anyone even wants what you are building). Another thing to consider is the psychology of progress. Momentum feeds on itself so it is a good idea to set aggressive timelines. 3) Theoretically, no one cares where you live. Practically, it may help to be in a tech-dense area for networking, hiring, etc purposes. 4) Not doing enough (any?) marketing is probably going to be why most technical founders fail. The problem for the most part if not whether or not you can build a thing, it is going to be whether or not you can get enough (any) people to buy and use the thing. You should be doing twice as much marketing as coding as a rule of thumb. 5) Fundraising is a tactic, just like any other tactic available in building a company. There are some ideas that are capital intensive (eg high customer acquisition costs) and would be hard to execute without fundraising. If you do decide you need/want to fundraise, you should understand the implications for you and your company and plan accordingly. For some reason, lots of people seem to form their identity around bootstrapping or VC. I don't think this is a useful way of thinking about the topic. It is better to think about it as a tool and decide if that tool is what you want or not.