I am Brandon, I made a living from a financial management website I built in college. Ask me anything!
Back in 2005 I built a simple website so I could manage my bank account and credit card purchases from my laptop. This website I had running locally on my computer allowed me to track my purchases, income and would output some spending reports. As a broke college student working a minimum wage job, I noticed my expenses were outweighing my income each month. I showed these reports to some friends and they said they could use this website too since they had no idea where their money was going.
This made me realize there was a market for an online money management tool so I spent a few weeks updating the website from something I built for myself into something that would allow other people to sign up and use. In May 2006, I launched ClearCheckbook.com. This was back before the iPhone existed and there weren't any basic financial management tools available that didn't cost an arm and a leg.
In 2009, when the company I had been working for went bankrupt, I made ClearCheckbook my full time job. Today, the site has nearly 500,000 users managing over 125 million transactions.
I currently live in Santa Fe, NM and aside from managing my website, I spend a lot of time cycling, baking bread and brewing beer. I'll be happy to answer any questions you have, whether it be how I made the leap to working for myself full time to what I do in my free time.
Dec. 22 edit note: I'll be on and off Reddit today if there are still more questions that people want to ask.