I am working on building a web-based project management software application. I am really bootstrapping to start off with, and really want to try and take on a partner as a cofounder. The hard part is, I am a bit of a control freak. But, I want to break away from this, and try and divide and conquer rather then try to go it alone.
When you started, did you have a cofounder? Was it someone you knew or a stranger that complimented your skills? What advice would you have?
My cofounder was a stranger and it's gone incredibly well but I'm honest with myself regarding the type of personalities I butt heads with and took a hard look when meeting people to find the right fit. My cofounder when we met said he took the meeting because I had actually done some work to get this going meaning I had already done a lot of research and had started wire-framing so it's not like my cofounder was walking into something were no work had been done. If you're not technical you need to prove your value and not just send your tech cofounder off working diligently while you're waiting for them to build it. Also you're going to need to curb those control freak ways because no one is going to want to get involved with someone that isn't willing to allow someone to add their input to the project. If you know that's just the way you are I'd recommend work for hire but even then people don't just want to be lemmings.
When you say you're "really bootstrapping" does that mean you're actually funding this or it's sweat equity? If it's the later I don't know if I come on.
If you don't have somebody in mind already you're courting disaster. This isn't the kind of thing you just figure out in a month or two. It's like getting married.
To your broader question - should you have a cofounder - the answer is yes. While you'll find outliers of successful single founder startups, they are few and far between. A solid cofounder doesn't just fill in a skills gap, they provide a trusted sounding board that allows you to make better decisions.
That all said, finding and choosing a cofounder is where things get really hard. You will work with your cofounder for more hours in a day than you spend with anyone else in your life. Friendship alone doesn't get you there. It's about having complete confidence in their capabilities and judgement so that you can truly delegate.
I tried the co-founder route and it was a disaster. Basically co-founders should be people who:
a) You have chemistry with. You can "feel" they "get" your idea and they complement you.
b) Ideally you have worked with before in some capacity.
Short of that getting a co-founder just to round off your team you'll feel that sooner or later the marriage of convenience will fall apart. Don't do it just because its on the checklist.
(Accelerator GP here)
It is possible to go it alone, but we're noticing that the people who do the best have a partner with whom to share the (sometimes unimaginable) workload. If one of you can sell/run the business while the other writes code, so much the better.