Here's my story.
I wasn't sure what to do with my life. I had been teaching English overseas and then as a part time instructor on a college campus in California while doing a master's degree in TESOL. Xbox came out with the XBLIG program, I started looking into it, and at one point, I decided to go all-out and quit my master's degree program and try to make games (still was working part-time at the college, plus sometimes substitute teaching at the public schools). This was in 2009-2010.
My first couple games were text-based CYOA which did far better than you'd expect text-based games to do on the 360, but hardly sustainable. Then I teamed up with Bill Stiernberg and made a NES-inspired JRPG, Breath of Death VII: The Beginning. It didn't sell a ton but for a time, it was the highest rated XBLIG on the service. I think a big part of this was the fact that we decided to price it at $1 - whereas most of the $1 games on the service were complete garbage (along with many of the higher priced ones), here was a full 4-6 hour comedy JRPG priced at next to nothing.
We followed up with Cthulhu Saves the World. Since BoDVII took us about 3 months to make, we thought CSTW would be about the length, but it ended up taking us about 8 months. We released it around Christmas and like BoDVII, it didn't sell a ton, but it was reviewed well.
We knew we had to get off the XBLIG so we did a little Kickstarter (long before Kickstarter was a thing) to help fund a PC port and raised a few thousand dollars. We also managed to convince Valve to let us their service, largely on the strength of our positive XBLIG reviews. Since we were priced at $1 & $3 on XBLIG, they wanted us to sell a bundle at $3 and we agreed. We had one of the very first JRPGs on Steam and it did really well. For the first time ever, we were making enough money to survive so I quit my other jobs.
While we were finishing up CSTW, Penny Arcade contacted us and said they were impressed with what we were doing and asked if we were interested in finishing up their RPG series for them. We were fans & thought this would be a great opportunity so we agreed. PA3 came out and did decently, but we still had to make a PA4 to finish off the series. Worried that PA4 would sell worse, we did a brief promotion before launch where for a day, we gave away PA3 for free. That seemed to do the trick - although PA4 did sell worse than PA3, it didn't sell much worse.
Now all this time, I wasn't storing up huge amounts of wealth. No, typically, by the time a new game came out, I was down to my last penny and/or asking my parents to bail me out with a loan until we started getting royalties for the new game. We wanted to try to break the cycle so we thought we'd do a big game funded by Kickstarter and that would be our big claim to fame, our breakaway hit that set us up for life. At the same time, Shane Bettenhausen from Sony came to us and said that he loved our stuff and we had to get our next game out on PlayStation. So we set up a deal where Sony would help us with marketing & provide free PS4 codes to our Kickstarter backers and in exchange they got timed console exclusivity (which didn't really matter since it's not like Nintendo or Xbox cared).
Cosmic Star Heroine went up on Kickstarter and managed to do low 6 digit figures. We probably messed up in not doing stretch goals since funding died down drastically once we reached our goal, but on the plus side, we weren't on the hook for a bunch of extra features. We started development and then we seriously missed our release deadline. The game was more ambitious than we had expected, I was new to Unity (previous games were made with XNA) & Vita performance was so bad on my initial attempt several months in that I had to go back and rewrite a ton of code just to get it to sort of work (and then later, I had to rewrite even more to get the RAM usage down so it would work on actual Vita's and not just devkits). I ended up borrowing a LOT of money just to survive until we launched and I was a complete emotional wreck. And then the game came out and it wasn't the huge indie success story I had hoped for. Don't get me wrong, it did okay & we've made decent money from it over time (ports & physical releases have really helped) and in the end, I'd call it profitable, but it wasn't the "this is going to change everything" game I had hoped for. On the plus side, although the review average wasn't anything special (7s & 8s), some people LOVED the game so it was great to feel like I had made something that I could really be proud of, that if it had been released back in the 16-bit RPG days would have been looked back on as one of the good games of the era.
So I made some adjustments. My family & I sold the house that we had a mortgage on, moved out of the country - we were living in California and we have a bunch of kids so our living expenses were high - and moved to countries with low costs of living which did wonders for my stress levels. In 2 years, we travelled between Taiwan, Japan, Hong Kong, Korea, Singapore, and Malysia and spent way less money per year than we had been spending in California. I finished the Vita port and finally got over my trauma of making games and so about a year ago, we started working on a follow-up to Cthulhu Saves the World - Cthulhu Saves Christmas. It's not this hugely ambitious game, but it's funny & it has a cool battle system & neat graphics & music and I hope that the gimmick is neat enough that people will pay attention to it when it comes out later this year. I don't need to take out any loans to reach the finish line this time. I'm stressed about the game and how it'll be received, of course, but I'm not the emotional wreck that I was at the end of the development of Cosmic Star Heroine, and I'm looking forward to finishing it & being able to start on something new.