Evaluating startup offers
excitingrole.com
excitingrole.com
Enjoy the ride. Most startup fails, so everything in evaluating an offer has to take that in account.
Make sure you bargain for a great experience to put in your resume for the next gig. Make sure something survive out of the startup when it fails, like keeping a blog on the side talking about your challenges is a great way to ensure your portfolio endures.
When you evaluate your stock options, the right ratio to which consider it is.. zero. If you are a provileged employee and truly believe in the project, go for equity. Company will be limited lyability anyway early stages and stock options will likely never vest.
If you are a side project junkie, try to bargain stock options for a relaxed non compete so you can keep your midnight coding exploits profitable.
Make sure the tech stack is marketable. Both in technology terms (java node whatever) but also in direcion: intelligence and analytics go always well on any resume.
Do try and engage anyone involved in the startup, from ceo to customers. Idea can be had for free and learning a businnes space with it's workings and pain points is always worth it. Be helpful to anyone and grow your network. You gonna need that always.
Last, don't let the starup consume your life. It's just not worth it.
In my experience the challenge of working in any stage of organisation is fighting its disfunction. If you love your field of work, then this will be likely your only nemesis. A prime benefit of working in a startup is your relative power to do this. So embrace it and use it as a place to learn how to get stuff done. This will serve you well wherever you eventually end up and expose you to people and functions well outside your domain.
Given that:
1) Is what they are proposing reasonably sensible? Ask someone normal if unsure :P
2) Is it interesting to you?
3) Do they seem like intelligent, friendly people?
4) Challenge them on a product/architecture decision they have made and see how they respond.
5) Ask how much runway they have and be comfortable with it
Finally, you only live once, take a chance, really try to do something new. When your there, speak up. If your lucky you'll have a good experience with good people and learn a hell of a lot.
I start with #4, it gives many clues about #3 and may reveal things about #2. For #1, don't ask friends, ask prospective customers.
1.) Tell me about a situation where you disagreed with your team, but trusted them and was convinced. 2.) Tell me about another one of those. (There's always one canned answer)
In other words: Who can tell the CEO "No" and do they know when to listen and when to push. If the CEO doesn't know how to do that well, I think the company is doomed, and it's incredibly hard to do well.
My guess is that this is especially dangerous for startups. Think about it, you're a founder and you've been told "No" by investors, experts, customers, thousands of times. Now all of a sudden you've proved them all wrong, you've built a business and it's starting to show promise.
But to scale, you're going to need some of those experts who told you "No". If you're building a car, you're gonna need to hire some people that have run a car factory or managed a complex supply chain. You're gonna need to trust them when they tell you, "I need 6 months, 3 months isn't doable". Or not. Maybe you're right, you can push beyond the possible. Maybe you're wrong and you can't, breaking your team and product in the process. Which one is right? You choose. But don't screw up, it's all on the line.
I think this is one of the least appreciated traits of the giants. Musk, Jobs, they pushed their people to the breaking point, but clearly they also knew what to drop and what to insist on to get things out the door. Quoting Jobs, "Real artists ship." Jobs famously argued against an app store, then was convinced and then pushed on it as hard as anyone.
I could go on, but the point is this kind of decision is fiendishly hard, and I think it separates the great from the mediocre.
Basically: make sure to get a fair salary down the road, or at least make sure you learn something that you otherwise couldn't (and makes it easier to find a better paying job in the worst-worst case scenario).