What concerns should I be worried about when thinking about selling my startup?

Im an investor and advisor. As many people as you ask, you will get different answers. The best and most successful way to raise capital is to start with people you know, aka friends and family. If friends and family are insufficient as they often are, then you need to find angels. If you dont know anyone, network. They arent hard to find. It might be a good idea to find a few prominent local people to serve as advisors and get their help in raising money. The worst part about raising money is that it almost always deflects from running the business. If you want to discuss this further, Im available.

Wow, lots of questions here. Let me try to hit them in order: "Should I get a job or find investors?" IF you have access to enough investor capital (not debt and not your savings) and you can get to MVP and still maintain ownership of a sizable majority of the business then do it. IF that means debt financing then only use the debt lines the cost of which can be carried by returns generated by the use of funds. I would prefer to offer a convertible note to prospective investors that can be easily extended throughout both friends and family and seed rounds (up to $2M to $3M) to get to proof in the market. If you can get to revenue and earnings fast enough then you can avoid equity dilution all together. IF you cannot secure that find of funding AND you cannot produce enough revenue from your business to deliver sufficient earnings for you to live on, then by all means, you should find a way to make the money you need and not burn all your savings or mortgage your home If that means short term contract work that's great. Particularly if you can find log term work that is relevant to the business you're building. If that means taking a job then do that. IF you do that, then yes, be transparent with your employer and let them know you're working on your own business also. Hope this helps....

A prototype will not get you an investor, to be honest. This is just a fallacy. If you can fund the prototype, launch it in the market, get some traction from users. See if your mobile app resonates with your users. You need to track whether your app is able to retain those users so that they keep coming back to it. If you have a good amount of retention with the first few set of users (100 or 1,000), that's a good pitch to take to an investor. Investors are not looking at ideas, they're looking at businesses that can get, retain and engage a customer.

Yo are talking apples and oranges. Capital gains are related to your basis not the form of payment. If you are a cash basis taxpayer, you pay taxes when you receive cash beyond your basis. We can help you with structure.

I would look to see what stage you're at as a start. I've ben through this many times. 1. First study the VC and the partner 2. See what else he has invested in 3. They may be looking to round up their vertical with something similar or to acquire smaller players. If you're not a competitor, then anything is game. 4. Study when they invest and how Lastly: 1. Set up the call. 2. Start the call by letting them talk a lot first. Ask: What is your mandate, sector? What do you invest in? What stage? What do you look for? What is the typical investment size? Where (geographically) do you invest? This will tell you a lot about why they are reaching out and what you should say after. Hit me up privately if you would like to discuss more, and good luck!!!