The CEO and the “other” Cofounder

There are three ways to be a bad founder. The worst is asshole because it actively slows you down. Crazy is a weird one because you can be really effective and nice, but nothing you do is making sense or helping.


I probably lean most into the crazy side.

The best one to have is someone nice because someone nice wants to be successful with you. Only an asshole would continue be incompetent or an asshole.


The best way to be CEO is to start on your own for awhile


Only after make substantial progress do you recruit someone. Ideally that someone is someone you started bouncing ideas off of for awhile.

The best way to be the “other” cofounder (CTO, etc) is to have a list of ideas you think are great and see if anything close to those ideas falls into your circle and try your best to be part of those. You really want to be looking for ideas that inspire you and you would have started on your own so you come at it with your own perspective.

Either way, your biggest fear will always be whether what you are doing makes any sense and whether you are working with the right people.

I’ve been CEO, CTO, and just the non-CEO co-founder in the past with startups. In the end, the work is what it is. You play to your strengths. The titles matter more to people on the outside. They just want to know who to blame and congratulate when things are going bad and well. The big decisions should and will be discussed out and generally decided by consensus.

As Amy Buechler, the Batch Director / Therapist for Y Combinator said:

“If you make a big decision without approval OR against consensus (slightly different), I think it’s safe to assume you’ll pay for it in trust. Trust is an extremely important currency and should always be tended to like a young garden, so I’d move forward thoughtfully if I were you. In all the hundreds of founders/founding teams I’ve worked with, I can’t remember a time that surprising the founding team/company with a major change in priorities, direction, etc. was necessary, well-advised, or the best path forward.”


How to be a good CEO to your cofounders

It is always easier to be the CEO. You are in a position of power. You can move around your cofounders if needed. Imagine having a problem cofounder, now imagine if they were the CEO and how much worse that would be for you. You may wonder whether you should negotiate higher equity or salary. Or seek higher status by going off on your own.


Define the long term roles as early as you can

Clear delineation of long term roles is good especially early on. Also be clear on what roles you share. “We both do customer support during these hours, you handle marketing, he handles design, you handle finances, etc.” One time things like names, domains, locations should be mutually discussed and shared and in the end they don’t really matter as much as your product and sales.


You are on the same team solving a problem together

My best cofounder consistently started conversations with “What do you think we should do?” and I returned the respect. We put them all down and weigh them. Our best ideas have come from those mutually respectful conversations. When I screw up, they don’t outright blame me but ask me how they can help to make this right or prevent it in the future. When I see you screw up, I’ll act the same. I generally mirrored how they treated me.


Communicate more than you are used to

Big disagreements tend to happen more when there’s no or declining revenue. I might even start doubting your ability as a CEO.Maybe it’s because I think I’m ok at sales and can start my own company, but I am constantly paranoid if my CEO is up to par.


The nature of sales is you only see the result of a % of your effort. It makes it look like you’re not working as hard as tech so you maybe have to work harder than the tech guy and be more transparent than you are used to with all the things you are trying. For the love of god, don’t start “playing CEO” prematurely. What is “playing CEO” you ask? Have ever met someone who spends most of their day talking about their startup, but you never see them working or improving? You can have all the funding in the world and I’ll leave (and have before) immediately because I know its pointless if the guy at the top isn’t productive.

As CEO, you may find your work does not yet translate well into weekly deliverables that your cofounders have such as shipping features or producing designs.

You will need to communicate results or effort.

It’s a trade off, obviously results is best. But effort if not.

Effort would things like always being present. First one to wake up. Handling emails and responding to leads or customers quickly. Staying up to make the phone call to someone in another timezone. Reading up on some topic we know nothing about but needs to be experts fast. Dealing with the tedious stuff of a startup that has to get done like the accounting or compliance or following up on someone. Weekly deliverables would be more discussing some of these things he did and what went wrong or what we might want to think about.

If it’s results like when they close a big customer or an acquisition :D, then obviously I give a ton of slack if I think they aren’t being productive. I just think okay they know what they’re doing.

Be rich or be king

Unless you have decent sales and I am making a good tech salary, I would expect near equal decision making & equity or I would be out of there very quickly. It’s a tech company and I’m head of tech. I may accept some inequality, but once I see we are struggling and still pivoting I would expect more if we by some miracle made it work. This may be different for other cofounder roles but I suspect motivations will be the same.


When it is all working great, it looks like this

The CEO will ask me what he could be doing to help me. When I said we need better SEO, he wrote weekly company blog posts and talked to some experts about what else we can do. When we agreed to redesign our site, he made several different banners in sketch. He then went even further and linked me to several different well-designed sites he thought I could draw inspiration from.

Also, I ended up helping in return when I had downtime. When he was more transparent with how he followed up with our customers, I was able to automate that quickly. When he showed me how annoying it was to look up specific data for customer support, I made it easier for him to access in the product.