Preceden [1], a tool for making timelines, was profitable almost immediately. Heroku costs about $50/month and a premium account costs folks $29, so with 2+ upgrades/month it is profitable. Currently making ~$700/mo.
jMockups [2], an HTML5-based web-design tool, was publicly launched about 4 months ago and is still not profitable. Costs total $200/month and with one paying customer, I've got a ways to go before profitability (but it's progressing very well).
Recent blog post has more details:
http://www.mattmazur.com/2011/03/february-in-review-life-tra...
AR will, knock on wood, probably hit cash-flow positive in May (about six months after launch) and pay back development costs in a month or two after that. I was originally targeting 12 months for surpassing BCC & consulting but, knock on wood, I have since learned something about my market which may make that pessimistic.
I had been basing my projections off of running a medium-volume low-touch business with average yearly account values in the $500 range. It turns out there is an addressable market for which average yearly account values are in the five figure range. More detail on that in a blog post Friday-ish.
1) First one was an ISP, boot-strapped. 4 years. Mildly profitable, sold to a larger ISP.
2) The next one was a short stint with a e-retailer. They were almost immediately profitable, but needed some serious cash to grow. So it sold within a couple of years and the founders all still work there. It's wildly profitable now, but alas none of the founders can capitalize on that success outside of a steady job.
3) Next one was a NLP middle-ware company (yes, they exist) that had been around for more than a decade, I came in near the end and worked there for 3 years. It sold right after I left (I didn't have equity). I believe it was unprofitable.
4) After a few years bouncing around mega-corporations I came back to startup land. We're 4 years in. Just hit profitability this year and then the Congressional funding disaster hit (we're almost entirely government business). We're going to see if we can make it through, but we may end up selling.
5) My wife and I just launched our new company www.kymalabs.com (her main job, my part-time job). We'll see how long that goes! We'd actually like it to grow enough to pay our bills and give us long-term employment, but who knows!
"Neuro-Linguistic Programming middleware? Eh?
Bootstrapping and being just one person made it feel so much longer than I had hoped when starting out.
Each month I look at the revenue and determine an arbitrary amount to pull out for myself.
FYI, I do not write code. We have three very part time developers building it.
Current biz: launched in 2009. Still working on profitability. This is a long tail business so I've learned I need to be patient.
Third startup (the one I'm building today was lamen profitable after 6 months. Don't expect it to grow a lot more until we get some funding, since the next steps require a lot more than lamen to succeed.. (ah, the great wall between MVP and V2)