I think one of the hardest things about scaling up a business is deciding when to hire and who to let into your family. SOLOSHOT is still quickly sliding past the point where I REALLY know everyone who works for us... there are people that I know more by their HR profile than anything else. That's not a shocking statement for any large company, but it is for us.
We're fighting the constant battle of WE NEED SOMEONE RIGHT NOW and trying to find the person who we want standing next to us in the trenches. To a certain extent, all size businesses face this problem. The difference for a company of our size and stage is that one person can truly change the temperature of the entire business.
I've always been pretty good at trusting my gut despite being someone who has been called "calculated". Gut instinct is how I chose a college, a first job, a breakup, and a career change. That being said, it's hard to just say "trust your gut" when hiring or firing. It seems like there should be some other hard metric that dictates success or failure. Unfortunately, I don't think there is one. There only thing you have in your toolbox is time. Spending a lot of time with someone and exposing them to lots of different people in the business.
I don't have a conclusion or an answer to the hiring question. Mostly, I just have gratitude for the opportunity to work through these types of challenges and conversations.