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Every CEO goes through times when they say to themselves “things just aren’t working.” While this might very well be true, what is not true is the feeling that generally accompanies it: “I’m all alone and this is a unique problem.”
After seeing startups from the inside and outside, from seed rounds to billion-dollar companies, I can definitely say that all problems CEOs experience are repeated. Across board meetings, CEO dinners, coaching sessions, leadership retreats–I hear the same startup problems mirrored back to me time and time again. Here are the common ones:
1. I don’t have product-market fit
2. I need money to run my business but investors don’t want to give it to me
3. I have product-market fit but I hate my job
4. We aren’t making progress against our goal
5. Critical people keep leaving my company

When you have one of these problems and you don’t know what to do, it is easy to feel stuck. But you are not alone, many others have solved very similar problems in their own companies. This guide describes the most common reasons behind these problems, and how you can solve for them inside your company.

CEO problem one: I don’t have product-market fit
If you don’t ever find product-market fit (PMF), your startup is fucked. You might not have product-market fit if:
• You aren’t growing
• You have high churn
• Your product is hard to sell
• Customers don’t seem to care that much

What this feels like is constantly being stuck in the early phases of a startup: messing around with new product ideas, getting no traction, going back to the drawing board.

Another variant of this is that you’ve gotten to a middle-stage because you either did have PMF at one point–or you thought you did–and then you scaled up your team. This can be even harder to get out of because you may have a lot of momentum with a customer base or an idea that isn’t really working anymore. It can be hard to pivot what you are doing because of the very public commitments you’ve made to employees, customers, investors, and, most importantly, yourself.

Pre-conditions for finding product-market fit
I won’t explain how to find PMF; there are other great articles on how to find product-market fit, for example the one from Rahul Vorha (CEO of Superhuman). However, I will explain the necessary pre-conditions for finding PMF and what the usual blockers are:
You need to decide who your customer is. At Justin.tv (a live video broadcasting site), we could never decide who our primary customer was. Was it the viewer? Was it the broadcaster? What …