I quit

#1 - Optimize for the CHANCE of success, not the magnitude of it. Don't worry THAT much about the % of ownership. Worry about winning.

#2 - Do worry about control and don't give it up. Plenty of investors don't require you to. "If you take money from anyone, like it or not, he is your boss :)" - that's simply not true. You ARE responsible to him, but you don't have to turn over the keys, nor do you have to turn over 50%.

#3 - Get a co-founder. ;-) Spreads costs, and increases likelihood of success and gives you a nice excuse to have a majority of the board seats.

I thought you had friends who were willing to help you out...

Take money from whoever you can - friends, families, and fools. You're not at the investor stage yet where people can eat you alive, and you can just refuse it if they try to. Keep well funded if you can; don't wait until you're out of cash, as investors know you'll be in a bind and will use it against you as much as they possibly can.

Taking money from friends would add motivation (or stress, but you seem like the type who can handle tight situations) and resolve to getting your startup off the ground, so I would recommend you pursue those initial starting funds.

Taking money from someone does make you responsible for that money, but doesn't make him your boss. They're called investors precisely because they give you money and hope to make a return on it - they don't have time to boss you around. Also, if you take money from someone, it means that they believe in your product, which is a great boost to morale especially if you're going in alone.

Finally, there are other ways of raising money besides selling your company - I know convertible debt is one choice, but I'm not familiar with any other low-cost routes (besides YC).

While it's true that if you use debt financing, you're ensuring that you succeed or else, but consider credit card debt: Most credit cards have a high interest rate that compounds each month. By using credit cards (and carrying your debt more than a month or whatever your grace period is), you're increasing your expenses and your burn rate.

It would be better (IMO) to secure a business loan. You'll have a much lower interest rate and a longer time to repay - not to mention the easy regular payment plan.

Still, I prefer equity financing. 10% of a watermelon is more than 100% of a grape.

Money isn't the only thing you take from investors. Especially in the early stages, it's not even the most important thing. Their contacts and experience are more important.

If you succeed the credit card is a better choice If you fail the investors path is the better one.

But you're more likely to succeed if you take smart money.

"That's not advice, that's half an advice."

What would you like him to do? Come to your home town, drive you to the airport and escort you to Silicon Valley personally? Raising money is not mysterious or poorly documented. Don't act like it is.