I quit my startup because of comic sans

Okay, it wasn’t really caused by the Comic Sans.

I had very fun 3 months of pretty fun collaboration and intense learning, but in the end I had this very clear feeling that I would be better of on my own.

It wasn’t awful, but it wasn’t great. There were many small and big things that were making our fit non-ideal, and I had doubts growing in me, and one Sunday night, a pick deck in Comic Sans topped me over the edge to call it quits.

Company vision fit

Both my partner and I wanted to build a profitable company that would be bigger than just the two of us. But he was extremely focused on getting investment, when I was more interested in retaining control and bootstrapping as much as possible.

It makes sense, I’m practically self sufficient - I have lots of money saved and invested, skills that could easily give me money from contract work and skills to build and (even) market the product.

On the other hand my cofounder was more dependent on others, had limited runway, higher monthly burn, and much weaker technical skillset. It made a ton of sense for him to be securing funding.

Funding company with venture investment can be pretty useful:

• there are some types of companies with high startup cost that are not feasible for a typical ‘bootstrapper’
• acceleration of growth - no one wants to go through a slog if you could make the growth faster
• a blanket of security before you reach profitability

But it has a cost:

• You give away equity
• You put time into securing funding instead of making a useful product, it takes a lot of time into making pitch decks, getting known around, etc.
• it shapes the type of a business - ideally, it would be a ‘unicorn’ and investors will push you into this direction even if it makes the business fail in the end

I’m not sure what I want exactly, sometimes I think that I want a lifestyle business, sometimes I think I would like to make it big, but in either case I want it to be my decision and not due to pressure from investors.

Work style fit

I found my cofounder work style to be chaotic. We would make a plan, he would pick a lot of items to do, but then everything would be in progress, but hardly anything really done unless there was an external deadline, like for an accelerator application. We would agree for a system for tracking tasks, but then he would not use it for the most of the time. Was that necessarily a deal breaker? Not really, people can have different styles and still get work done. I wouldn’t force people who have many years of experience to change their work style just to suit me, but it also didn’t make me feel too good about it.

And there was also an aspect of attention to details. Which was not my cofounder strong suite and that was leading to a bit of frustration and rework on my side. I wanted to build a high quality product and that is at odds with low attention to detail.

The issues above don’t make my cofounder a bad entrepreneur, I think that a dynamic, slightly chaotic work style with lots of work in progress could work for some people, but I just found that I prefer people who are more methodical and steady.

Skill fit

I brought to the table very strong development skills, ability to execute quickly on the product. Thanks to my earlier product building adventures I also had plenty of ideas about idea validation and marketing and some experience with content marketing, SEO and paid advertising.

My cofounder brought the idea and the ability to talk to customers, many years of tech/consulting adjacent experience and “street fighting”. Ideally, he would also bring in marketing and design skills, but he was pretty green to marketing and not particularly design inclined.

With a non-technical/technical cofounders, the typical split would be to have a CEO and CTO, which would make me the CTO and give other important tasks to my partner.

However, what makes me interested in entrepreneurship is handling all those CEO things. I’m actually interested in business. I wouldn’t want to delegate those aspects of the entrepreneurship. That combined with my partner being new to this, made me resistant to this partnership.

Friendship fit

Turns out we had very, very little in common. Sure, we were focused mostly on working and the business, but during the time we were hanging out I haven’t discovered a single shared interest apart from wanting to start a business.

And even though we lived in the same city, it was quite far apart. And we had different lifestyles - he was a young father, living in the suburbs, me - tech person leaving in the downtown, doing many sports, etc.

On top of that, we had differences in the background. I’m pretty much a nerd: science, hacking, technology, fitness, finance. He was more of a businessy-consultant “people person”. And we would have differences of opinion based on that.

Idea?

Was the idea a killer idea? The jury is still out, it was a very interesting project from the technology perspective, and I could see it working from the business perspective if we executed it very well. It wouldn’t be a particularly easy project, but it had potential.

But at the same time, I think I can do better in terms of difficulty of making it a successful business and skill fit for me. I don’t have a better alternative right now, but I will keep looking and there is always an option to start a boutique software solutions agency which to be honest also sounds like a lot of fun and an easier business to bootstrap.

It was pretty difficult to abandon it, I got really invested in building it, there were more things I wanted to finish, but it had high opportunity cost and working hard on it was wearing me out.

What’s next?

After 3 months of intense learning and building while also working my day job I am going to be taking a bit of a break and instead work on non-critical side projects. I will also invest time into researching and validation of some new business ideas, but probably won’t jump full on into implementation.

Did I make a good decision? The time will tell, I think that it was right to go with my gut, because likely these many small problems and doubts would only get bigger with time.

Going on my own with the next project will for sure be hard and lonely. But I have the indie community and friends, it won’t be too bad!

Everything being just on me is a bit scary, but I did that in the past, I am very independent and I like to be in control. I got this! I’m not giving up on my entrepreneurial dream!