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Ask HN: Has a hobby or side-project of yours ever became your main vocation?

3 points by wuliwong ↗ HN
I have worked on a lot of side/hobby projects in my nights and weekends over the years. With some of these, I had hopes to eventually build a profitable company or obtain seed funding and pursue the effort full-time but I have never reached that goal.

I would love to hear experiences of anyone who started with a side/hobby project and built it into a company. Was starting a company your goal from the start? What challenges did you encounter and overcome through the process? And of course, what's the business!?

4 comments

[ 5.0 ms ] story [ 22.7 ms ] thread
jppope
My first business: I wanted to play in bands but could never keep a group together so I started throwing concerts for all of my friends bands (promoting). Turned into a pretty good gig after a while.

A: I did not intend to build it at all. It totally just happened. A: There were tons of challenges. Booking venues, Booking Bands, security, cleaning, professional sound...

wuliwong
Nice, that's very cool. I have noted in my life that keeping a band together is like 4X the difficulty of keeping a romantic relationship afloat. The 4 in 4X is really just the number of people in the band. :)
ksaj
In the late 80's / early 90's, I ran a service that collected and transferred Usenet news and email betwwen BBS systems and the rest of the world (using UUCP). Eventually I got a live Internet feed to run it all more efficiently, and very regularly dealt with adventurous hackers continually breaking in to my server. I actually didn't hate that because none of it ever got destructive, and I thought it was wildly clever. The pre-web Internet was a whole different world compared to now.

Over time, keeping my hobby business together taught me a whole lot about what eventually became known as a firewall. I was continually building firewall features (which I referred to as a fortified gateway because firewalls didn't really exist yet) and creating test cases to find new vulnerabilities and guard against them first. It was heavily influenced by a sort of "audit" script that was making its rounds that identified poorly configured (vulnerable) services, except that I was scripting cases for vulnerabilities I was finding on my own server, and also by watching what the clever hackers were up to. I got to know a lot of them personally, funny enough.

It was actually a lot of fun. Otherwise I would have just given up and worked at McD's or whatever.

When BBS's started to get their own more efficient feeds and didn't need my silly slow service anymore - in the mid 90's - I was approached by a company that built firewalls (they finally became a thing!), and ended up working in infosec ever since.

My intention was to raise enough money from the side hobby to put out an instrumental metal album. No album yet, but I certainly made a career out of penetration testing that lasted decades. Now I'm winding down, doing more advisory work, leaving the grunt work to the whippersnappers.

So, if you're looking for a wicked lead axeman, ring me up. Eventually I might get that album happening.

wuliwong
Hah, cool story. It's interesting that both the comments were from musicians. I too am a musician myself. Sounds like things have worked out great for you. I think there are two different general ways of thinking. One is to do the lean startup model and be very scientific and iterate through ideas quickly. The other sounds more like what you did, build something that you like and just keep working on it because you like it. The second camp seems to insulate you a bit from the thing having to be successful financially in order to be a fun and rewarding aspect of your life.