I'm a very proud person, and I'm proud of what I've accomplished. That being said, you're right about coming off as negative or ashamed. I don't actually feel that way about myself or my efforts, but I realize that it may not look that way over the internet.
In fact, I had intended the "downright embarrassment" bit as a joke. Still, thanks for pointing it out!
I've noticed a slight difference in how we in the midwest talk compared to how the west coast (Seattle and SFO) talk. In particular, I'm not perturbed by the writing style and I see clearly a confident young man who is building experience. In the midwest, often, modesty and humility are required for most public conversations. One way to express that modesty is to be quiet (think 'tough cowboy'). Another way to is be self-deprecating (sometimes it comes across as false-modesty), which is what you do. And yet another is to talk about the other person or make small talk. It's something we all do from here. On the west coast, in contrast, there is a common desire to talk oneself up either by referencing a pedigree, accomplishments, or trajectory. As a simplifying stereotype these descriptions don't apply to all people or all the time.
I would take away two lessons from this discussion.
1) The midwest modesty we both use is somewhat foreign to other cultures. Don't feel like you have to change yourself, but, don't be surprised that different people will understand you differently.
2) Focus on the product before fixing any analysis or blog or other meta-startup thing!
In fact, I had intended the "downright embarrassment" bit as a joke. Still, thanks for pointing it out!