Ask HN: Should I accept a CTO position without much experience?

If your doubting the decision to begin with, you already know the answer. Don't turn to the internet to figure out what to do with your life.

Lesson #1: Trust yourself to make the right decision to move you forward.

As others have said, the key points are that you should ask for at least a barebones salary and you will likely be replaced if this company takes off. However, this could be a great opportunity and you shouldn't let fear or self-doubt drive your decision.

One thing I'd like to add, assuming the financials work out and everyone is happy, is that moving from CS/programming to a CTO position is going to require quite a different skillset. You probably won't be programming all the time, at least not after whatever project they have in mind is in a stable place. You will potentially be responsible for reporting/BI/analytics, systems architecture and administration, tech support (Yes, everyone is going to ask you for help with their computers), and anything else tech-related that comes up along the way. If you want to stay in good shape as a programmer, you'll be responsible to find the focused time to code, keeping your skills sharp and current, and staying motivated to do so. At this time, you'd normally go work with an established development team who can guide and mentor you, as well as balance the team so that you have time and resources with which to further your skills.

The only thing in your post that makes me think this may be a good opportunity to explore is when you mention entrepreneurship as your long-term goal. This is likely going to be a great crash-course in how difficult that can be. My advice, though, would be to get great at what you know and learned, spend a couple years on a great dev team, save some money, and I bet there will still be opportunities for you to get into a startup for all or mostly equity.

Hope this helps. I'm just a young guy who's seen some different sides of the equation.

I think if you have the drive to become an entrepreneur, you will. My experience, really quickly, is: Intern programmer, two years college, two years working, one year entrepreneur, at my current job for three years. I spent one year doing freelance consulting and development, and it was a blast. I had fun, but didn't make quite enough money to live on, and found a job I was happy with. I freelance on the side now. But I'd do it full-time again in a heartbeat if I could save up some money and line up some steady monthly work. I don't think starting your own business is everyone's plan. From how you're presenting things, I personally think it's very likely that you will leave the "comfort zone" you mentioned. My reasoning: It won't be your comfort zone. I've never felt comfortable just doing a 40-hour week, and I think that underlying entrepreneurial spirit keeps me from being comfortable with the mediocre and ordinary (which my job isn't).

I also hang out with a couple people that bootstrapped their own product/service while working a full-time development job and they now run successful businesses by themselves, after running it "on the side" for 1-2 years.

Having seen the OP's personal site, I may have been a bit harsh. He could well have the tools to succeed and if he accepts this position for no pay then his employers are getting an absolute bargain. Shame on them if screw him over as he seems like the kind of person you really would want on your team.

I wish OP good luck and success.

You were an intern there and there were no other engineers? Was it a paid internship or were you their free engineering labor? Now you are going to graduate and get a real job. Their free technical labor is leaving so they offer you a CTO position for no pay until funding? You are most likely getting screwed.

If for some reason you really believe in this company and team and are willing to go without pay, you need to be a cofounder with 10-20+ percent of the company (depending on the number of founders). You are the only technical person and they need you enough to make you CTO.

Anything less and you should run. If they do get funding, as others have said, expect to be replaced, possibly prior to vesting whatever stock you did get. You need a large percent ownership and a single trigger acceleration clause in your contract so you get your stock when they fire you for no reason. [1] Even then you can get diluted to nothing, but with a large percent ownership and accelerated vesting it will be more challenging.

You better really trust these people, believe in the mission, and get a large percent ownership with the right contract. Any hiccups or hesitation from them and you should walk, unless you want to learn first hand the dark side of startup bullshit where you gamble with no pay to make other people rich.

[1] https://www.quora.com/What-is-the-difference-between-single-...