I was thinking something along the lines of a portfolio of work or LinkedIn profile to get a better sense of your skills/identity. I actually have a scraping project related to a nonprofit grants prospecting startup and wanted to see if you would be a good fit for some work.
I think scammers, even the ones in Nigeria, use a wide variety of tactics. I think it's prudent to be wary in a situation like this, where the OP is explicitly looking to offer services for money in an unusual situation in what will likely be an unconventional transaction.
Hang out at top universities. People there are ambitious and always looking to work on stuff - and there's usually an event or club or two that you can attend where you can meet like-minded, action-biased individuals, even of you're not a student.
1. The person on Twitter doesn't exclusively ask Ryan about the business. He specifically asks how he spends his day. Even if the asker wanted to know more about the business and less about his day, Ryan's response is appropriate given how the question was phrased.
2. Ryan does talk about which business activities he focuses on. He specifically mentions how he used to handle newsletters, wireframes, support emails, and marketing plans but now focuses on strategy, product, and team communication.
3. Ryan is a CEO of a venture-backed company and people, including ones on HN, are sometimes interested in the lives of people like him, both the personal and professional aspects. The personal details he shared helped me understand how he's able to maintain work-life balance, notwithstanding the demands of a CEO, which I find personally useful.
4. As to your complaint of him specifically mentioning his iPhone, one of the other commenters put it best: "Because his identity revolves around the brand of his phone and he's just begging for your validation. OR The post is full of specific details and he owns an iPhone."
If you want Ryan to be more specific, you could ask him on his blog. But I think it's unreasonable to expect that Ryan should have had the foresight to be more specific, and then subsequently criticize him for not being specific.
You might like Durham, NC. Small town feel with a slower pace compared to the big cities, but a decent startup scene with a few local incubators and universities nearby. If you want to work for a big company, Lenovo and a couple other big companies have campuses nearby.
Hackers also like living and working near other hackers in a hacker-supportive community.
Also, if you're a Berkeley or Stanford grad, you probably prefer living in an exciting city like San Francisco instead of staying in suburbia. And even if you personally don't, your friends will, which means SF is still the place to be.
I've started and stopped programming, but feel like http://www.teamtreehouse.com has been really helpful. They have lots of videos to help fill gaps in knowledge, with a bunch on building web apps from start to finish, including RoR and other languages/frameworks.
To offer a different perspective, I disagree with jnorthrop and think your value proposition is clear - you're helping companies encourage customers to share purchases and provide metrics of how that sharing affects the bottom line.
Under the ABA's Model Rules of Professional Conduct, providing legal advice without a license potentially could be considered "practicing law without a license" or, for licensed attorneys, the creation of an attorney-client relationship, which creates duties for the attorney.
I was in a similar position as you: C++ experience from AP Comp Sci courses in high school, CS106X (accelerated intro-level CS course at Stanford, ended up majoring in something else), and Wordpress hacking from various projects. Worked through Rails for Zombies, why's (poignant) guide to ruby, but none of them really stuck for me.
www.teamtreehouse.com OTOH, has been great. easy-to-understand videos with logical progression.
I'm really curious how you outsourced your app development. Have you written a blog post about it? I'd love to see some of your documents that you used to communicate with the outsourcing team and a list of books/sites/references that helped you accomplish what you did.