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?
Good hell, I feel like no matter what I do, I keep making the wrong decisions! I feel like I’m not cut out to be a Founder. There has to be someone out there that’s killing it while I’m hiring the wrong people, talking to the wrong investors, and going after the wrong customers. What am I missing here?
My startup is long since out of money and I’m doing everything I can to keep the show going. I feel like I owe it to my investors, staff, and customers to make this work even though at this point everyone has pretty much abandoned me. They would tell me if I should stop killing myself, right?
At some point after we’ve been so diluted by investors, are we really “Founders” anymore, or are we just glorified employees with a little bit of stock? At what point is it no longer worth sticking with our startup and may be worthwhile to just go start something else?
Are there any benefits to being a Founder who came from nothing? What kind of behaviors or expectations might they have which are an advantage at a startup company and why?