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

"It sounds like you are being given the opportunity to build someone else's Minimun Viable Product for free!"

I second this. I have no way of evaluating the character of your boss, but there are warning signs all over the place.

My story: I was hired to build a MVP (did -eventually- get paid) and due to various missteps, it turned into a one man job (I was the entire IT staff for 4 years). Part of those missteps were me being work-obsessed (a bad trap to fall into, it leads to burnout) and the other misstep was that these founders, who had no experience in IT, were all psychopaths (as in one had a criminal history of fraud, the other should have been jailed long ago). I failed to do one of the basic tasks of business, which is know who you are dealing with.

They used my "enthusiasm" which in the IT/startup world is quite necessary, and leveraged it against me. I certainly knew enough at that point in my career, but it got lost in the need to keep things working. Eventually I wised up, when a customer made legal threats because they had been blatantly lied to about the product they were buying.

I, as nominal CTO, had not been paying attention to the sales process and stupidly was relying on the others to take care of that area. It was then I realized the full nature of the whole operation and how I'd been taken advantage of - so I quit. I reasoned they were going to fuck me over one way or another down the line, so I'd better get out.

Less than a year later, the CEO abandoned his wife and kids (she owned 51% of the company) and now they are still fighting it out in divorce court. The CEO turned out to have a 25 year history of fraud and cheating even the companies he worked for.

So ... the people you are dealing with --may be-- great, but you have no real world experience in how businesses are run or how life actually is at the C layer. Read up on the Sociopaths/Clueless/Losers theory - it is a valuable thing to know, as it explains a lot. I've seen shades of it over my 30 year career in IT, but it never hit home till I did this startup.

And if you are really CTO, and a salary of $0 is being offered, why have you not mentioned the percentage of equity offered? If you really are going to be responsible for hiring and designing the tech side of the company and ... you should be getting a large chunk of the company. It is irrelevant the company already exists - by being an official CTO, you are taking on a lot of responsibility.

No offense intended, I'm sure you're capable of programming and all that, but ... I wouldn't hire a 24 year old with just a few years experience as CTO. The Master's is irrelevant in this situation - there is a lot of non-IT social type knowledge needed, IMO. The politics of business is nasty stuff, and your stereotypical engineer (i.e. me) likes to stay out of that stuff; it is a skill set you have to either like (and so you're an asshole) or you just get used to it. I've always tried to stay out of it, hence the 15 year career of contracting.

I think my advice is, if you want to stay with this company, then say you want to be "Lead Architect" and leave the management/business stuff to someone else - then you can expect to get a salary and will only be tangentially exposed to the business/political crap that typically goes on - that way, you get some valuable non-IT experience safely and some tech experience too. When (not if, this all doesn't sound like a winner) the company crash and burns, you'll have some useful profit out of it.

No problem.

It'll be good to get an understanding of "if you're not being compensated by salary then what are you compensated with?"

It sounds like you're literally taking the same amount of risk as your boss and for that reason, you should have some share in whatever rewards that come out of the risk taking.

Money to survive has to come from somewhere (i.e. loan, parents, savings, etc.) but it definitely doesn't appear out of nowhere.

Also, evaluate the product. How long do you think they can reach the point where it's revenue generating? In the absence of revenue and cash runs out, will they start to fund raise again? Will all the other expenses be comfortably covered by the current cash pool?

It also comes down to a lot of luck as well. There's really no right or wrong answer here and no one can say for sure if it'll be a success or not. But that's the fun part of life. And trust me, even if you have a normal software engineering job, the success is also always down to you. And the benefits are that you manage to build relationships with other talented software developers and you'd be bringing in money that you can save to start your own venture in the future. Many people have also been very successful starting companies later down in life.

Nothing is ever a dead end. Every path has a pros and cons. It's ultimately up to us to open our minds to see it and leverage it.

It seems a glorified internship to me. Experience may be interesting, even good, but no money upfront? Meh. You will get ton of paid opportunities if you are as smart as your posts here. Good luck.

If you are confident with your programming skills and believe this startup has bright future, accept it. Otherwise, join another company to gain income and experience.

Btw, are you in the US?

No, but my plan was to go to the US for my first job. I already passed a few interviews.