Man, I logged in just to comment here.
From my perspective one top reason people don’t leave the Valley is because it’s its own kind of safety net. If they get tired of their job or want to advance their career, there’s a whole host of local VCs ready to make intros, companies looking for that perfect head of such and such and former coworkers who might forward along an opportunity.
Being out of the Valley (and being remote — to reference Johnathan’s last post) makes that harder. You can’t grab coffee with a founder, you don’t attend goodbye parties with people who are going somewhere you might want to be in two years, more than half your friends aren’t even in your industry. Sure, there are a lot of push factors driving people out of the Valley, but knowing that you’ll never be unemployed for long is quite the strong tether.
The way to beat that if you’re hiring from east of Tahoe is to play up how vibrant the local startup community is. Sure, that might be harder if you’re in the middle of nowhere, but Austin has a great startup scene. So does Toronto, and Portland and Denver. Being in the California bubble means we might not have heard of your local VCs, or not realized that many up and coming startups are based in there. So let us know about them. Make sure your hiring target sees a future for herself in a new town, even if your company takes an unprofitable turn (or doesn’t take a profitable one).
PS: I also wanted to mention that in dual high income households (which are the norm here), it’s a real perk that you can live grandly on a single senior tech salary. I’m not sure that applies in Toronto, but it’s definitely a much bigger draw than shoveling snow.