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 Isn’t Anyone as Committed as the Founder?
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?
Raising Money is a One Way Street
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 am I “Too Old” to Launch a Startup?
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?
Why Selling a Startup Brings No Validation
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?
When do Founders Get a Raise?
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?
What We Lose When We Sell Our Startup
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?
Should We Focus on Profit or Growth?
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!
The Benefits of a Hard Reset
“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)?”
When is the Right Time to Give Up Equity?
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?
All Founders Make Bad Decisions — and That’s OK
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?