Quit My Job To Start A Startup?

What You Should Know Before Doing This

Cory Kennedy-Darby
4 min readMar 15, 2015

I’ve wanted to discuss this topic for some time and finally the inspiration for this came from a post on Reddit called, “Quit my job take the plunge on my own ideas?”. This is my background, I’m a software developer, I’ve worked at a handful of startups(MediaMiser, Leapshot Labs, Vectorface) and more recently I’m the CEO/Co-Founder of GamerBet.

What To Expect With Startup Life

Emotional Roller coasters

Ups & downs happen all the time but the giant drops will mess you up. @scott

When non-founders ask me to describe what it’s like running a startup it can be summed up in one phrase, ‘emotional roller coaster’. There are a lot of components involved in running a startup ranging from vision, fundraising, product, sales, marketing, legal, etc.

Here is an example that I had to deal with in January. After more than a dozen emails back and forth I was able to get an in person meeting with investor Gary Vaynerchuk. Of course I was thrilled, I packed my bags and I flew to New York for the meeting. The night before the meeting I received an email saying that the meeting had to be cancelled due to the winter storm. Fuck. All sudden that excitement nose dived and I was left with nothing but the feeling of failure.

Depression & Failure

The struggle of running a startup with everything on your shoulders. @adam

Prior to starting GamerBet I wouldn’t have described myself as someone who had dealt with depression but since starting it has felt like I’ve struggle with times of depression. You might ask, how can someone become depressed from running a startup? Well as a founder I’m responsible for everything that happens. This includes the stuff most people will argue isn’t my fault but ultimately there is no one to blame but yourself as a founder. There are three other co-founders(Collin, Phil & Sabrina) and every day I’m one decision away from failing and or letting them down. Now let me ask you, who wouldn’t get a little messed up from that? The amount of pressure on your shoulders day to day is extreme.

Before Quitting

Minimum Viable Product (MVP)

Pitching PlayerBet(GamerBet) at Startup Weekend Event

The video above shows what had been accomplished in a weekend. There’s no excuse to not have something in place before quitting your job. If you’re unable to find the time, passion or drive to work your normal 9–5 job and then work from 7–12 on your startup I’m not sure quitting your job is the right choice.

Self Awareness

Stick to who you are & your strengths. Build around your weaknesses. @skrubu

I have a strong opinion that not everyone is cut out to be an entrepreneur. When attending tech or startup events I’ve meet plenty of people who from my view are lying to themselves. They will try to explain that they want to start a startup but usually it is followed by plenty of excuses to why they can’t right at this present moment.

Founding a company requires you to be able to take a step back and be realistic with yourself because you’re going to need to know what your strengths and weaknesses are in order to build the company. Personally I’m able to take a step back from myself to know that I would struggle running any startup without a co-founder because I have very little self motivation but instead I am driven by the guilt factor of knowing that I’m letting my co-founder(s) down.

Usually Forgotten

Developer != Business Savvy

Amazing Developer? Maybe you’re shit at running a business though. @lynsey_wells83

I’ve had the pleasure to work with many brilliant developers over the last +5 years but honestly only 3 have ever came across my mind as being solo founder material. The reason there is such a difference is that there’s a lot of developers that in my opinion would be absolute garbage when it comes to running a company because they have not spent the time developing their business skills.

The statement that is usually used to argue out that my point above is invalid is something along the lines of, ‘If I build a great product the customers will come’. There’s many developers who have built amazing products that nobody know about, that have a terrible business model and are more in line with a side project than building a startup.

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