My learning as a Fortune 500 VP and a 2x start-up CEO is this: you can do the CounterOffer thing once. Once. Then you are tagged as "loose" and somewhat unreliable. You'll get the $$$. But the next promotion may be impacted. In any event, you can't do it twice. The second time, they let you go.
It's true. Sometimes, until you get big enough, you can't provide a career path in the short term. But you can at least make someone that is truly great a lead, and let them know as you grow, you want to find a bigger path for them. At least, you can tell them you want to do this. Sometimes, they will need to go to achieve their goals if you don't grow fast enough.
But, if you grow fast enough ... this resolves itself.
In general, it's working out for now ... for now ... because the best start-ups are scaling faster than ever. As long as start-ups scale faster, they still get incredible leverage even as fully-burdened costs grow. In SaaS, the best start-ups are getting from $2m to $10m ARR in 1 year now. That was pretty close to impossible 5 years back. The markets are larger. With more customers, you get more revenue. And you can pay more. For now.
The single worst thing you can do in my experience in a fast growing start-up is make a terrible key hire. I wrote about how making a terrible hire as my first VP Sales almost ruined EchoSign ... The Year of Hell: http://saastr.com/2013/11/06/if-your-vp-sales-isnt-going-to-...
Once a week for sure when you small, and with your direct reports. Once you are bigger (say 50-100+ employees) and have more indirect reports -- it's hard to meet with all of them every week in an unscripted fashion, especially when most don't report to you anymore. If you force yourself to do it once a quarter, especially in the functional areas you work less on ... it will make a huge difference.
