I more or less paid for my computers selling a shareware¹ calendar program for Macs. It just let you make a one page calendar² of a month and type things in the days with some simple styling.

I initially wrote it as a birthday present for my brother, who needed something to do that job, then decided maybe some other people would like it. It was popular with teachers. (Writing that I feel like a jurassic patio11!)

I think it was $10, then I raised it to $15. These were pre-internet days, pre AOL even. It was fun getting checks from foreign lands, though it annoyed my bank. They eventually started charging $20 to clear a foreign check, so I had to adopt an unofficial “foreign folk get registered for free” policy and just thank them and tear up their checks when they arrived. I think the last check came in over 10 years after I stopped maintaining the program.

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¹ Slightly nag ware. Registered users could make the solicitation screen stop showing up on launch. There was a secret little click dance you could do on the solicitation screen to prove you were registered.

² Pro tip: A “calender” passes the spelling checker, but is a machine in which cloth or paper is pressed between rolls until smooth. You will have to update your software and reprint your paper manuals when you discover this fact.

Bonus Pro Tip: If you try to write a direct SCSI access disk utility, you may accidentally corrupt your only hard drive, not have backups of your source code, and then get to write a block scanner using only floppy based tools to scan the wreckage of your hard drive looking for blocks that might be C source code, collect those together, and reassemble your software sources as best you can. That's ok, version 2.0 is always better anyway, and you will have learned to keep backups.

So perhaps not much of a story, but the Amiga came out and the first (for me) compelling "dungeon crawler" game on it was Dungeon Master. I spent a lot of time on it, and as was my custom, kept notes in my notebook. Pretty soon I had a pretty complete set of maps for the place, which a friend of mine wanted a copy of. So I made copies of the pages of my notes but they were hard to interpret (except for me!) and disorganized, so I opened up Deluxe Paint and just drew them (they were all 32 x 32 squares I believe) anyway, the drawing lead me to go in and check things, and I went back and looked for every single secret room etc, and end the end had a complete set. So I printed them out and gave them to my friend, who offered to pay me $5 for them.

I wondered if anyone else would want them, and so I offered them up, a copy for anyone for $5. Sold a couple hundred copies. And to top it off, a German company that made 'player guides' bought a copy, decided they wanted to use it in one of their guides and offered me $50 for the "rights" to do that, and I gladly accepted.

That ended up funding my purchase of a lot of games for the Amiga.

I don't know about selling, but I had a hobby project, my first in Pascal, that would translate ProBoard (ProBBS, or a PcBoard door program that did fancy things) to and from RBBS (the other open source board software). I uploaded it to a couple of boards, some of which were FidoNet connected. Anyway, a few months later got a call I think from someone somewhere in the Navy that wanted to use it, and asked if I had any improvements planned. I didn't as I had already moved on to other things (probably Lemmings), but let them know they were free to use it as they see fit. As an 8 or 9 year old kid, I was amazed at the reach of technology, so it was very encouraging, and helped me to pursue a career in IT.

Coming from a somewhat different viewpoint other than as a developer, I spent 10 years working as a full-time reviewer for one of the largest shareware disk vendors, Public Brand Software, and then later for Ziff when they bought PBS. (In fact, my first day at PBS was also the day Ziff took over the company...)

There was a lot of money being made from shareware in the 80s and 90s. I was involved in the Summer Shareware Seminars (later rebranded Shareware Industry Awards) and got to talk to quite a few developers/authors who were making mid-6 figure incomes from shareware, and of course there were a handful that had made their million(s). They were pretty aggressive marketers, though, and not the kind who just wrote a program, distributed it through the BBS ecosystem, and waited to see what would happen.

Disk vendors could make a considerable amount of money, as well. PBS was no Mom-and-Pop affair. Thinking back on it, there were 25-30 full-time employees (office staff, order takers, tech support, reviewers, catalog editors, in-house disk duplicating staff, 20+ line BBS, etc.) I have no idea what type of revenue the company generated, but it was a bustling place!

I had two wildly (for me anyway) successful Windows shareware apps in the '80s & '90s. WinPrint[1] and INIedit[2].

They were $25 a pop and I made way more than $10K from them over the years. Each payment (except a few juicy site licenses) came to me as a check in an envelope.

The best part was WinPrint became my resume for Microsoft. It demonstrated that I was an expert in an area where demand was high: Apps on Windows that could actually print.

[1] http://www.kindel.com/products/winprint/ [2] http://www.kindel.com/products/iniedit/

As an exercise in Windows programming I made a little alarm clock program called SuperAlarm that would use Winamp to play MP3s. I put in the readme that I liked Skittles and postcards; I got a number of postcards and one day I got a 1-pound bag of Skittles from someone in Canada. I still remember how great that felt even 15+ years later.

Haha, I found a screenshot of the app: http://www.softpedia.com/progScreenshots/SuperAlarm-Screensh...

I gave away and eventually sold snippets of front end web tools (example code mostly) shortly after picking up basic JavaScript/HTML/CSS skills as a pre-teen in the late 90's.

My first product was a "login" script (just JavaScript which generated an encoded version of a username and password and navigated to that URL). I remember when I received my first envelope with a $10 check and an email address inside. That was an awesome feeling.

I also made a fairly complicated "calendar creator" script which allowed a user to stylize and customize a calendar template that would be output in the form of HTML, CSS, and JavaScript. Since HTML, CSS, and JavaScript were the only tools I knew how to use that's naturally what I wrote the program using. Everything was output in a textarea field for "easy" copy-pasting into the user's website.

After a few years I realized the programs were becoming dated (I started receiving more frequent refund requests) and I stopped charging and open sourced them.

In hindsight, the programs were fairly poorly written but I'm glad to know that at least a couple dozen people found them useful.

Yup. I wrote AutoCAD add-ons. Public domain and some shareware. The "big money" was in site licenses. Architects wouldn't pay for anything. But anyone doing work for the government was serious about making sure they had licenses for everything.

Promotion and distribution were major challenges. You'd upload your wares to CompuServe, BBSes, etc. I'd also visit conventions and tour user groups. I never felt the need for classified ads (not targeted enough).

The real shareware players had their own BBSs. I went a bit further and started a network of CAD/CAM, computer graphics themed BBSs and served as the hub. Much like FidoNet. It was huge fun, but a lot of work.

Someone else noted that majority of income came from consulting/contracting and some writing. That was my experience too. I had the view "your work is your resume" and publishing shareware was the best way to get known. Much like working on some open source projects today.

In the late 90's, I began selling several command-line programs for Windows using the shareware model. I sold a command-line SMTP mailer (MailSend), a command-line POP3 reader (MailGrab), a command-line scheduler (TSched), and a command-line Dial-up-networking disconnect utility (HangUp).

Total income over several years was in the low five-figures when bundling deals were included ( some people wanted to include these programs as part of bigger systems that they sold ). I created a successor to MailSend called MailWrench that provided better support for Microsoft Exchange Server and SMTPS (SMTP over SSL), but the market just didn't seem to be there for command-line mailers any longer.

These programs are now free-to-run software with source ( with the exception of MailGrab).

We did fairly well.

http://books.google.com/books?id=mi8EAAAAMBAJ&lpg=PA29&#...

Good times...

In high school I wrote a turn based strategy game (think "Empire" with resources, like a very very basic "Civilization") and sent it off to a shareware publisher. The Internet and self-distribution wasn't invented back then.

I was pretty disappointed when I received the rejection letter.

I used to compile a bunch of tech-product-related coupons and discount codes and tricks for saving money on buying the hot stuff of the day (RAM, DVD-ROM drives, etc) and sell that as a report on eBay.