Cofounder doesn’t excel at anything. Need help!

I have been working on different startup ideas one-after-another for the past 10 years. Finally, I built an enterprise product with product-market fit. I spent one year building the product. After I acquired 2-3 customers, another person joined me. I was NOT looking for a cofounder, but he was looking for a job.

I respected his person very much. I had worked with him at the same non-profit for last 10+ years.

We started with 20% equity for his share and then reduced it to 15%.

This cofounder has been with me for last 12 months. We tried him at Sales, Customer success, operations, software testing but he does not seem to excel anywhere. Although he is close to 50 years old, he is not able to take ownership of anything.

We are a bootstrapped company. Our resources are scarce. I could pay him, or rather hire a part-time person for the same amount. I would prefer to hire a part-time person.

What are my options? I think I will be better off without him than with him. I think about him more being a drain on the business, rather than helping the business.

  • This is OP here:

    My concern is this:

    He gets involved in every discussion. It is easy to say that I am a business/management guy even though he does not know much.

    I feel really sad that he has so much equity and has no outcome from his action. I have spent my life on getting here, and he is getting it without any effort. He does not deserve it.

    The worst part is that he is my friend.

    • Adding on to this – not to above commenter. Did you have an agreement with your cofounder that his shares would vest? Did you even have a formal agreement?

      A way to be fair without being a dick would be to buy his equity back from him. You might be surprised how much he values it.

  • Have you tried telling him exactly what you described here? Have a sit-down, tell him its tearing you apart that you cant find a suitable position for him and you dont want to ruin the friendship but that in your mind you feel it would be best to part ways.

    Afterall its his shortcommings here that are the problem so make it his problem, dont carry the burdon for him. In short friends and family are for taking long walks with, not run a business. If you let it fester you can be sure the friendship will get ruined in the end and your business wont be doing any better carrying around dead weight all that time. The outcome is clear, its just a matter of timing.

  • Can you quantify his contributions? Maybe he is not as much of a burden as you think, but only does “enough to get by” versus “excelling at something”, which I think is perfectly reasonable as a lifestyle.

    Maybe you can work on a quantified feedback concept for both of you together, so everyone can have an honest and objective conversation about the topic together. With an objective feedback system he can learn about how much of a burden he is by himself and maybe even change his ways. Nobody loves to be a burden. Quantifying such things (like number of sales, hours worked, contracts subscribed, lines coded, calls made per day, whatever is important to you both) is an artform though and can be pretty tough, you’ll have to get help with this or get really creative.

    If he really pisses you off and you have authority, maybe you should end the relationship alltogether. It’s like in love. It’s hard to find the right time to break up, some people never find the courage to leave an exploitative relationship.

    On the other hand you could just take a deep breath, relax and see it as your way of doing carity.

  • I was in the same position a few months back. And what I can tell you for free is that that feeling will never go away; he will never be able to “earn his shares.”

    So, if you want to eat shit don’t nibble. Let him go. It will be hard for you in the future when you have to buy back the shares from him, but, remember, there won’t be a future if you don’t have a present.

    All the best.

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