Should we be talking about societal issues at work? Do leaders have the right to lock down what can or cannot be discussed at work? How can Founders and their staff find common ground?
I’m starting to wonder whether my co-founder is the right fit. At first, they seemed really engaged, and I thought we could build something great, but lately, I’m starting to second-guess partnering with them at all. How can I tell if this is the right person, and if it’s not — how do I get out of this?
Why can’t I find anyone to work at my startup that is as committed as I am as a Founder? I’ve created comp structures and upside, and yet I still feel like I’m the last person standing when it comes to really being committed to this thing. Is it me or is this just the way things at startups go?
I’m thinking about raising money but I’m a little concerned about how having investors might change my potential path. I understand the upside of having investors, but are there some downsides I should be concerned about?
When I finally exit my startup, am I going to feel that sensation that Tom Brady must feel after he wins Superbowls? Like a ticker-tape parade to my victory, only the ticker tape is made out of $100 bills and my arm falls off from high fiving everyone?
As a Founder, when do I get a raise? Everyone else seems to know that every year we (try) to give everyone an annual bonus, and when market conditions are such, a significant jump. But when does that filter back to my wallet? How do I establish reasonable expectations for myself?
Is there any downside to selling a startup? I always read the big headlines about how much Founders sold for, but after that, I never really hear from them about how it went. Is there a cost to selling a startup that no one talks about?
We’re starting to make some money — that was the point, right? Now, what do we do with all this cash? Should we re-invest it in growth or pocket it and live like (very poorly paid) kings? We don’t want to slow our growth but we also want to make sure this thing stays viable!
“I’m staring down the barrel of having to do a massive layoff at my company and tear down tons of work and decisions we’ve made. This feels awful. Is there any way to look at this situation as a positive, and if so, what should I be optimizing for (other than hair loss)?”
I’m thinking about using some of my equity to make a big move in my startup, but I’m worried about losing too much equity in the process. When is the right time for me to give up some equity and when should I hang back and look for a better situation?