A Missive to Struggling Founders

"Found a company," they said. And you did. You had a great product idea, quit your perfectly reasonable job, and created a startup with two friends. When it came to deciding who'd be CEO, you volunteered, and your co-founders agreed. You got the job. You're in charge.

A few years in, you’ve had some real success. You raised a healthy amount of money from top-tier investors. You’ve got revenues and customers. At your monthly founders’ night, between rounds of Catan and complaints that nobody will trade you any brick, you can see that your co-founders are genuinely happy in their roles.

But you're not. Some parts of the job are going great. You enjoy working with customers and the product team. But financing discussions leave you uncomfortable. Customer escalations keep you up at night. Sales and marketing problems leave you feeling lost and out of your depth.

You’re struggling. You’re starting to be unhappy in your work. Your spouse says you look grumpy a lot. Increasingly, you find yourself paralyzed in the face of decisions. The board has started to notice your discomfort and is checking in more often (“Do you want to grab a coffee?”). You’re not the same person you were two years ago. Everyone can tell that something's off.

Something needs to change. The question is, what? One of your VCs suggested an advisor who’s a top executive at a big-name company. Another thinks you should bring in Bain to work on strategy and go-to-market planning. Your co-founders think you’re just disorganized and need a chief of staff. You want to hire a CRO so you can finally free yourself from go-to-market challenges. Your spouse thinks you should quit.

You need help. But what kind? Do you need an advisor, an operator, a consultant, or a ticket out of here?

In today’s post, we’ll explore when you need each, what they can do for you, and how to figure out which kind of help you actually need.

In short:

• You need an advisor when you want to do the CEO job and need help thinking through decisions.
• You need an operator when you want someone else to own the work while you remain ultimately accountable for the results. The question then becomes: what kind of operator?
• You need a consultant when a specific problem requires a deep dive by experts, such as integrating an acquisition or moving to outcome-based pricing.
• You need a ticket out of here when you don’t want the CEO job enough to do what it takes to succeed. The question then becomes: a ticket to where?