In addition, I brainstormed on different possible uses of Twilio. I came up with a bunch of product ideas. One of them seems very workable because it is a partial replacement product for a bunch of existing products in the market. If I do decide to go ahead, I’ll have to pick the right time, based on the economic situation, business cycle, and other relevant factors.

In 1996 or 1997, I had done a research paper for one of my classes. The research turned out to be closely related to two of the core features of Twilio, but because of my work and other things, I have not been able to continue the work and create a finished product. But soon, after other things with higher priority in my life, I should be able to use Twilio to try the ideas in my college research paper and other product ideas I came up recently. 😉

http://www.twilio.com

It seems to me that you value the journey of doing a startup (ie enjoying the work and your team) more than you value the end and that you prefer feeling the risk over assessing the risk logically and objectively. For me, it is just not possible because risking a precious time and money in my life just for sake of enjoying the work without seeing the end is like playing a game of chess by just moving the pieces for the enjoyment of moving them without thinking far ahead.

Instead, I always find ways to deal with risks before committing to something, like a startup. Think of it as Texas Hold’em. It is just unwise to bet a lot without assessing the probability of you winning a pot.

Are you sure getting married is the riskiest thing you’ve done? From my knowledge of statistics on marriages and startups, I believe the probability of failure of a startup is higher than that of a marriage.

… unless the numbers you got is about a happy marriage as opposed to just being married…