I’ve watched tons of ‘once hot’ startups come and go, from Meerkat to Quibi, WeWork to Theranos. What are some of the things we can learn as Founders about how to manage our own startups when everyone is telling us how amazing we are? What are some of the pitfalls that come with the new hotness?
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’ve got a great plan for how to scale my startup, but I’m sort of wondering what happens if things don’t go to plan? How should I be thinking about my downside when most of my startup planning seems focused on growth and scale?
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?
At what point is it “too late” to start a startup? Is there a point where it’s no longer feasible to assume the risk associated with starting a company? Am I washed up as a potential Founder by the time I’m 25?
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!