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Ask HN: Leaving cushy job for startup (hire #1). Feed me your wisdom elder ones!

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Ask HN: Leaving cushy job for startup (hire #1). Feed me your wisdom elder ones!

#1
As it turns out, comfort bores me, a LOT. After trying the whole office job career thingy, I've decided it's either jump out the window or start taking risks again! (And promptly settled on the latter (I'm only on the third floor so it would only kind-of-hurt).)

However, I need a quick education on startup culture, jargon, inspiration, and how to avoid stupid mistakes. I know next to nothing about funding, dilution, employee compensation, etc. etc.

I want to be smart about this and make good decisions. What makes your personal list of the best no bullshit books / talks one should read before embarking on ye ol' startup journey?

I have asked for a reasonable salary (same as current) + equity. The company model looks like it will either get huge (already growing + actually makes money), or crash and burn like a glorious zeppelin due to regulatory issues. I find this very exciting as it's truly disruptive(TM) in a space that needs it.

If it does fail, I want to use this as a stepping stone / learning experience for a next venture. I do not, EVER, want to go back to boring 9-5 punch in and out life. After two years at a stable big-corp job, I've decided that it is my personal version of hell on earth (and I've been through cancer! which could come back any day! -- life really is short... and I don't plan to spend any more of it in meetings with middle management or building something that I don't own a part of just to make someone else rich... you know it's bad when hospital days feel like a welcome relief from daily routine). -- I also get bored of programming unless I feel I'm building something that matters or is challenging. I don't care about being a Professional Software Engineer, I just wanna build cool risky shit and play mad scientist with smart people.

Okay, now it's your turn to tell me what to shove into my brain before embarking on this journey (preferably in book or video talk form).

Re: Ask HN: Leaving cushy job for startup (hire #1). Feed me your wisdom elder ones!

#2
9-5 is shorter than 9-9, remember that.

Startups have a reputation of running developers into the ground. Corporate work, while boring at times, can be great if you want a work-life balance.

If you're going to be one of the first few hires, expect things to change as the startup fails to gain traction and the money runs out. Even if it successful, you'll probably find yourself in a management role as more people are brought in and you're the expert on the business domain (as well as the landing pages, marketing emails, CRUD apps, account details, etc.).

In some ways, a solid corporate gig can be more honest. IME you get hired for a role and you do that type of work. Maybe you haven't found the right cushy corporate gig?

Re: Ask HN: Leaving cushy job for startup (hire #1). Feed me your wisdom elder ones!

#3

9-5 is shorter than 9-9, remember that. Startups have a reputation of running developers into the ground. Corporate work, while boring at times, can be great if you want a work-life balance. If you're going to be one of the first few hires, expect things to change as the startup fails to gain traction and the money runs out. Even if it successful, you'll probably find yourself in a management role as more people are…

Hi, thanks I'm taking that into account. For me overwork is relative... I can burn out in 4 hours doing something I find boring or don't care about, then spend a weekend without sleep working on something a lot more challenging but interesting.

I would be okay with my role changing over time. Code is just another tool for turning ideas into things. I'm probably naive about some things, but one thing I'm sure of: routine is poison, comfort is overrated.

Re: Ask HN: Leaving cushy job for startup (hire #1). Feed me your wisdom elder ones!

#4
post #3

9-5 is shorter than 9-9, remember that. Startups have a reputation of running developers into the ground. Corporate work, while boring at times, can be great if you want a work-life balance. If you're going to be one of the first few hires, expect things to change as the startup fails to gain traction and the money runs out. Even if it successful, you'll probably find yourself in a management role as more people are…

Hi, thanks I'm taking that into account. For me overwork is relative... I can burn out in 4 hours doing something I find boring or don't care about, then spend a weekend without sleep working on something a lot more challenging but interesting. I would be okay with my role changing over time. Code is just another tool for turning ideas into things. I'm probably naive about some things, but one thing I'm sure of: rout…

I am not in a startup, so take this with a grain of salt. I have a number of people I talk to who have been in startups though, and a common refrain is that when you sign on very early you wear many hats - some fun, some not. Don't expect all your time to be coding, just like when you have a child you shouldn't expect all your time with that child to be play time.

I say this because if you burn out in 4 hours doing something you find boring then you might not be able to deal with everything needed. However another common refrain is that every startup is different, so you have to decide for yourself based on your read of the startup.

One last bit of caution. If you push yourself to the wall all the time then you might not have the energy you need when the time comes where the business really needs that push. From what I've been told, and from personal experience on a number of fast paced projects, it's better to pump out a consistent 40-60 hours a week with an occasional push to 80, than it is to do 80 every week until you crash.

Re: Ask HN: Leaving cushy job for startup (hire #1). Feed me your wisdom elder ones!

#5
post #3

Earlier quoted context omitted.

Hi, thanks I'm taking that into account. For me overwork is relative... I can burn out in 4 hours doing something I find boring or don't care about, then spend a weekend without sleep working on something a lot more challenging but interesting. I would be okay with my role changing over time. Code is just another tool for turning ideas into things. I'm probably naive about some things, but one thing I'm sure of: rout…

I am not in a startup, so take this with a grain of salt. I have a number of people I talk to who have been in startups though, and a common refrain is that when you sign on very early you wear many hats - some fun, some not. Don't expect all your time to be coding, just like when you have a child you shouldn't expect all your time with that child to be play time. I say this because if you burn out in 4 hours doing s…

[deleted]

Re: Ask HN: Leaving cushy job for startup (hire #1). Feed me your wisdom elder ones!

#6
post #3

9-5 is shorter than 9-9, remember that. Startups have a reputation of running developers into the ground. Corporate work, while boring at times, can be great if you want a work-life balance. If you're going to be one of the first few hires, expect things to change as the startup fails to gain traction and the money runs out. Even if it successful, you'll probably find yourself in a management role as more people are…

Hi, thanks I'm taking that into account. For me overwork is relative... I can burn out in 4 hours doing something I find boring or don't care about, then spend a weekend without sleep working on something a lot more challenging but interesting. I would be okay with my role changing over time. Code is just another tool for turning ideas into things. I'm probably naive about some things, but one thing I'm sure of: rout…

After the two weeks honeymoon phase...

Do a routine of 8 hour days that slip into 10 then 12. Five day weeks that then slip into six. For a year straight and learn that amount of energy and effort still aren't guarantees of success.

Imagine putting out fires all day every day and learning how to fix things but not having time to fix it properly so you're stuck in a loop of promising to go back and fix it right but just ending up with the problems.

Imagine being put in a constant state of anxiety and fear because sales don't turn out, code don't ship, marketing doesn't hit.

Meanwhile when you check in on Facebook now and then to see what your friends with the comfortable lives are doing and realize you're missing out.

For hard work.

That doesn't guarantee anything.

Good job getting same pay and equity though. That tells me either you're really good at what you do or the people you work with have no clue what they're doing.

Re: Ask HN: Leaving cushy job for startup (hire #1). Feed me your wisdom elder ones!

#8
"I also get bored of programming unless I feel I'm building something that matters or is challenging"

Keep an interesting idea of your own as a side project to do at home at nights and weekends. The startup is somebody else's idea. It may or may not be challenging to you, and it may or may not interest you after a while.

Re: Ask HN: Leaving cushy job for startup (hire #1). Feed me your wisdom elder ones!

#10
> I have asked for a reasonable salary (same as current) + equity.

Consider that the equity represents an ownership stake in the company, you are now a junior partner responsible for its success. No longer a flunky employee. This should impact your thinking and outlook on everything.

You will find Jay Abraham's 'Getting Everything You Can Out of All You've Got' excellent food-for-thought > http://www.goodreads.com/book/show/89969.Getting_Everything_...

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