Lesson learned: evaluate fit over the course of a month - if you don’t click then just move on. Don’t try to “make it work”, it won’t.
I’m writing this to share my experience as well as to reflect.
About 6-8 months ago Cofounder and I met on YC Cofounder Matching. The first convo was great - he had a lot of energy and optimism - but we were working on different ideas and didn’t have alignment.
Fast forward 4 months, we started doing weekly catch ups and we continued getting along. We both applied to YC and both got rejected so we decided we were going to work on a project together full-time and see how it went.
As founders, we both saw the problem of getting early customers and understood few (technical) founders understood how to do sales or had the bandwidth and we believed that sales should be done in parallel to product development. I always struggled to sell myself and after months of building would always fall flat.
The first week or two of the project started pretty well, we spent a lot of time brainstorming and researching. I could definitely feel his energy and enthusiasm.
We finally settled on an idea and began cranking away. It was at this point that I noticed a couple of things that really bothered me: his work quality was subpar (there were a lot of random typos and grammar mistakes) and I was working MUCH harder than he was. He even told me he was still “exploring his idea but for only 1 hour per day”. In the back of my mind this was absurd given that we had committed to working on a project full-time but I wanted to keep the project going so I ignored it.
The first mistake I made was I thought I could change him. I thought if I spent enough time leading by example and if we saw some traction he would be motivated to pick it up. Nope. As a matter of fact I had created a new problem, “our working styles were different” and “his voice wasn’t being heard”.
I explained to him that yes, I was driving this project and setting the direction, but that was only because I was working a lot more work and figuring stuff out faster. For example, I went through 10’s of hours of educational content; him - none. Yet he wanted to do it his way and it went against everything that the top experts were saying.
To keep the project going, I relented and let him have his way as long as he agreed to commit 8 hours a day, weekends off (if you ask me this is a joke for early stage startups).
We finally got our first 3 customers @ $200/m and this was a big break for me! At this point, he again brought up that our “working styles were different” and I could tell he wasn’t working the minimum 8 hours / day we agreed to. He sent me a cryptic text that I thought meant he was quitting so I said “Ok cool, it was fun working with you” to which he replied that his text actually didn’t mean he was quitting. Weird.
The same pattern kept happening for the next few weeks and just a couple of days ago we talked and he told me he was quitting (even though we agreed to work until the end of Jan). To be honest, I felt a sense of relief but also betrayed and disappointed that we had made a lot of progress and he was just quitting. I’m still figuring out how I’m feeling.
Lastly I’ll say this - my cofounder is a good person and I am by no means without flaws.
Lesson learned again: if you aren’t operating smoothly after the first month you probably will end up falling out.
I’m writing this to share my experience as well as to reflect.
About 6-8 months ago Cofounder and I met on YC Cofounder Matching. The first convo was great - he had a lot of energy and optimism - but we were working on different ideas and didn’t have alignment.
Fast forward 4 months, we started doing weekly catch ups and we continued getting along. We both applied to YC and both got rejected so we decided we were going to work on a project together full-time and see how it went.
As founders, we both saw the problem of getting early customers and understood few (technical) founders understood how to do sales or had the bandwidth and we believed that sales should be done in parallel to product development. I always struggled to sell myself and after months of building would always fall flat.
The first week or two of the project started pretty well, we spent a lot of time brainstorming and researching. I could definitely feel his energy and enthusiasm.
We finally settled on an idea and began cranking away. It was at this point that I noticed a couple of things that really bothered me: his work quality was subpar (there were a lot of random typos and grammar mistakes) and I was working MUCH harder than he was. He even told me he was still “exploring his idea but for only 1 hour per day”. In the back of my mind this was absurd given that we had committed to working on a project full-time but I wanted to keep the project going so I ignored it.
The first mistake I made was I thought I could change him. I thought if I spent enough time leading by example and if we saw some traction he would be motivated to pick it up. Nope. As a matter of fact I had created a new problem, “our working styles were different” and “his voice wasn’t being heard”.
I explained to him that yes, I was driving this project and setting the direction, but that was only because I was working a lot more work and figuring stuff out faster. For example, I went through 10’s of hours of educational content; him - none. Yet he wanted to do it his way and it went against everything that the top experts were saying.
To keep the project going, I relented and let him have his way as long as he agreed to commit 8 hours a day, weekends off (if you ask me this is a joke for early stage startups).
We finally got our first 3 customers @ $200/m and this was a big break for me! At this point, he again brought up that our “working styles were different” and I could tell he wasn’t working the minimum 8 hours / day we agreed to. He sent me a cryptic text that I thought meant he was quitting so I said “Ok cool, it was fun working with you” to which he replied that his text actually didn’t mean he was quitting. Weird.
The same pattern kept happening for the next few weeks and just a couple of days ago we talked and he told me he was quitting (even though we agreed to work until the end of Jan). To be honest, I felt a sense of relief but also betrayed and disappointed that we had made a lot of progress and he was just quitting. I’m still figuring out how I’m feeling.
Lastly I’ll say this - my cofounder is a good person and I am by no means without flaws.
Lesson learned again: if you aren’t operating smoothly after the first month you probably will end up falling out.