I'm a big fan of shopify, so don't take this the wrong way, but would you really be a good fit for someone with a baby and a mortgage? Currently, he's making decent money, with great pension and benefits, doing incredibly boring work. He could leave all that behind and work for shopify, for what? A couple fun years of lower total compensation without the security?
As someone who's finishing up college, I'd hop on that in a heartbeat. If I had a kid and a house, though? Far less likely.
Ok this is super difficult to answer because you only gave me circumstantial information instead of data that I need to make a recommendation. The questions that need answering are:
* How high is the individuals potential on an absolute scale?
* Is the current environment providing a steady way to reach this high potential
in a reasonable time frame?
If the answer is something like "high,no" then it seems to me that the opportunity cost of not coming to Shopify would be very high.
We are huge on work life balance because this is something that we can do much better in Canada then in the Valley. There are about 5 core hours in the day that we want people to be there ( 11 to 4 ) for meetings. We pay child support bonus, gym membership, catered free high quality lunch every day, we do tons of offsite events etc etc etc.
Now, let me read between the lines. I assuming we are talking about a dev position. The fact is that there is essentially 100% employment for great programmers. That's unlikely to be change in our lifetime. The reasons for that are complex but googling for "Software is eating the World" is a good starting point. Given this, it worries me when people talk about risking their pension and secure jobs. The only thing that's at risk in ones career is to not hit your personal full potential. If you don't agree with that then Shopify will not be a culture fit.
Also: A ton of people at Shopify, including me, have kids and mortgage but.
Great programmers are not immune from recessions, bankruptcies, layoffs, hiring freezes, and ramen-profitable rivals. By all means cash in, but don't bet on the music never stopping. I've seen it happen twice so far and I'm only forty. Bank a really healthy runway.
I don't know about working conditions at Shopify but I don't think the same mindset exists in Canada about working yourself into the ground for your startup.
I work for another startup - Wave Accounting. I left a fairly safe, well paying job to come here. I'm paid well, my work-life balance is great, and I love my work. And I have 3 kids and a wife who is in grad school (paying off my mortgage early helped with the decision, to be fair)
As far as the GGP comment, I know a few of the Shopify guys because they have a Winnipeg office and they're brilliant people. I'm sure it would be a treat to work there.
When you're young and feeling a bit adventurous or idealist, sure, make mistakes and try different things.
Keep in mind that the parent (top) said he's working in government, that's top-notch benefit that you can't get anywhere else. If startups can offer the same level of pay and benefit, even with risk, people will flock to startups.
Having said that, there's one more scenario that I've seen people prefer to choose:
1) Get a fairly stable job (albeit boring one)
2) Do 8-4PM
3) Work on side projects/hobby/small businesses on your free time
Why work for startups or small-medium companies where you may have to work slightly harder and get paid either slightly or way less?
I definitely see the appeal to that. Having some free time to work on whatever you want or even not to work at all is crucial and it just doesn't make sense for someone who has 3 kids and mortgage to pour all their time into startups.
As someone who's finishing up college, I'd hop on that in a heartbeat. If I had a kid and a house, though? Far less likely.