Photo via Bigstock

I thought launching a startup would be fun. After all, I was finally executing an idea that I’d dreamed of two years prior, which, until then, had remained nothing more than a note in my iPhone.

The idea was (and that’s literally all the 2-year old iPhone note said, “”), and it was an idea for a website where users could translate rap lyrics into English. Sounds fun, right? After all, what’s it really mean to be a balla, shot calla? (Note: according to our translation, it means you’re skilled at the game of basketball and well-respected by your local street gang).

After finally mustering up the guts and the funds to turn my little iPhone note into reality, I chose two former coworkers, specializing in web development, in whom I had a lot of faith and trust. These were guys I had enjoyed working with for over a year, and they had done an excellent job on the website for the company with which they were employed full-time.

I invited them out for happy hour to discuss the project and offered them equity (15% each) for coming onboard with the project and developing the website according to my specifications. That was my first mistake.

Lesson #1: Pay Hourly or Project-based; Don’t Pay with Equity

From the very beginning, I had problems motivating my developers to get anything done in a timely manner. I was racing against the clock to execute my idea, but it was like pulling teeth to get my guys to implement my requests. Even though we had started the project in December 2011 with a contractual completion date of March 31, the end of March came and went and the website was in no way ready for the public. I was forced to cancel advertising deals I had set up with publishers, and my frustration grew as one of my developers began failing to respond to my emails or phone calls.

Jayson DeMers

I pushed back the completion deadline to April 30 and took my developers out for lunch to explain the importance of the new deadline. On April 30, barely any progress had been made, even after repeated assurances that the site development would become a priority in the previous several weeks. I decided to remove one of my developers from the project entirely; he had never even signed the contract that gave him equity (apparently procrastinating on that in addition to the development of the website), so it was an easy split.

My other developer still retained 15 percent equity in the project, and he had been communicative and cooperative. The problem was that he lacked the skillset to finish the website. I had to buy him out of his 15 percent equity in the project because there was nothing else he could do for me. Awarding him equity only turned out to be an $800 strategic mistake (the price of the buyout), but it could have been much, much worse. His lack of the proper skillset to finish the website was my next lesson learned:

Lesson #2: Hire the Right People

Even though I’d worked with these guys for a year and thought I had an understanding of their technical capabilities (and work ethic), I was wrong. Because of my error in assessment, the project took 4 months longer than it should have, during which I was stressing and agonizing about the delay.

The people are what give your idea life and shape, so be sure to thoroughly vet the folks you select. Look for these things:

  • Communication: Does the person respond to emails quickly? Are they always available on chat? Do they almost always answer the phone? Do they promptly return missed calls?
  • Talent: Ask for work samples and really scrutinize them. Would you be proud to display all of their previous work to your own clients or customers?
  • Motivation: Does the person have the time to do the work? Do they have any other issues distracting them from focusing on your project? Do they enjoy the work? Do they need the money?

I began my search for new developers, this time turning to Craigslist and the WordPress developers jobs forum. I parsed through dozens of emails in response to my posting, and learned my third lesson:

Lesson #3: Have Patience, Don’t Give Up

By this point, the project was months overdue, and I had no developers working on it anymore (I had fired one and bought the other out of his contract). I called numerous developers who had responded intelligently to my ads, and vetted them over the phone for knowledge and trustworthiness. Finally, I found the right guy. He exhibited all the qualities I listed above (in lesson #2) and worked diligently with me to get the website finished.

However, the stress had taken its toll on me. I forced myself to work day and night, often working from 8:00am until 1:00am to keep the project moving forward. Looking back, I realized my next lesson:

Lesson #4: Take Time to NOT Work

Even though I was passionate about the project and wanted to spend all my waking hours working on it, I began to notice lots of errors when I didn’t give myself a break. The quality of my work suffered unless I removed myself from work and allowed my mind to clear. Heading to the gym and cycling would help relieve physical and mental stress, and was key to keeping my sanity.

But even through all the setbacks and the stress, I kept on going. And that’s because I really, truly loved the product I was creating. For years I’ve laughed and made others laugh at the hilariousness of rap lyrics when translated into English, and I wanted to build a platform for myself and others to do so. And that drive is what kept me going through it all, bringing me to my next lesson:

Lesson #5: Love and Use Your Own Product

You only get out of a project what you put into it; if you put your love and hard work into it, the output will be that much sweeter.

Lesson #6: Before Anything Else, Register Your Domain Name and Social Accounts

Before you can even begin working on your project, register the following:

  • Domain name
  • Facebook Page
  • Twitter Account
  • Youtube Channel
  • Google+ Page
  • Pinterest Account

There’s nothing worse than discovering that someone else has taken your company/brand name on a social channel. This happened to me with Youtube (someone else had already registered “crackerize” as a username). Luckily, I was able to secure the username at every other social channel.

Lesson #7: Identify and Avoid Legal Battles from the Start

These days, it seems like everyone wants to sue everyone else for something. With Crackerize, I wanted to display original lyrics of each “cracked” song so readers could compare them. Unfortunately, the cost of licensing the lyrics doesn’t make any financial sense (yet).  I couldn’t even use the instrumentals of the original songs with the cracked version of the lyrics due to licensing restrictions. Both of these roadblocks put dents in my marketing plan.

Identify and avoid any legal issues that might be associated with your startup before you begin.

Lesson #8: Throw Out the Bad Apples Before they Slow You Down

From the beginning, got off to a very slow start. Even though we originally kicked off the project in December 2011, by February all we had was a shoddy rough draft website that looked nothing like my vision for it. At that point, I should have recognized that I didn’t have the right people in place to execute my plan, and I should have taken action to remedy that rather than allowing the project to continue at a snail’s pace.

Lesson #9: Build Your Marketing Plan First, and Integrate it with Your Website

These days, social sharing is all-important for helping to kick-start a new web-based business. Keep this in mind when you’re building out your website so you can include proper sharing functionality. With Crackerize, I knew I wanted to use videos to assist in marketing the website in some way, so I had my developers build in a section for videos. Additionally, the website was built with shareability in mind from the beginning, so we never had any hitches when it came to building in that element of our marketing plan.

Lesson #10: Surround Yourself with People Who Believe in You and Your Product

I’m not a quitter, but it certainly gave me strength during the hard times to have a support group that included my girlfriend, friends, and family who encouraged me every step of the way. Not only did they want to see me achieve my goal of bringing Crackerize to life, but they all really loved the idea and are now members of the website. With their encouragement, I was able to keep pushing on through hurdles that included my own strategic errors as well as insufficient personnel.


I hope these lessons help you navigate the choppy waters of entrepreneurialism and take the step toward initiating your own startup.

For me, a 6-month development nightmare finally transpired into a beautiful, fun website; the manifestation of an idea I had over two years ago that sat dormant as a little note in my iPhone for two years. And no amount of stress I had to endure can take away the feeling of accomplishment I get now when I see and interact with the website.

Jayson DeMers is the founder & CEO of, a website where users can create accounts and translate rap lyrics into English. DeMers is also the founder of AudienceBloom, a Seattle-based SEO agency where he frequently blogs about SEO and social media marketing. [Editor’s note: Diving photo via Bigstock]

Like what you're reading? Subscribe to GeekWire's free newsletters to catch every headline


  • Felix Livni

    Dude, great story. Love your site. Still laughing. Today was a grand day, indeed.

    • Jayson

      Thanks Felix! I’m glad you like the site =) 

      And thanks for your comment, I really appreciate it!

  • Paul

    Crackerize? Really?

    • Jayson

      Yes, sir!

  • Alfredv

    Great article! I was thinking in taking the plunge myself. Question did you attend ant event in seattle area for networking? And if you did was it helpful?


    • Jayson

      Thanks! I don’t attend many networking events in Seattle because it hasn’t yielded me much in the way of ROI, but some people have luck with networking events.

  • Shalin Jain

    Jayson, this is a post every wanna be entrepreneur should read more so in the tech industry. Hiring is one of the most critical piece in the puzzle and tells a lot about how far you can get. 

    I shared my thoughts on #2 hiring on Tenmiles Blog:

    • Jayson

      Thanks Shalin!

  • Peter H

    Shouldn’t part 1 be “Don’t pay *contractors* or other short-timers with equity” ?

    Once you have people who will be with you over the long term, equity is one of the best ways I know of to align their goals and dreams with yours.

    Your point only seems to make sense with piece work — not with true long-term team members.

    • Jayson

      Well, my vision was to have my original web guys onboard with me throughout the whole project; they initially had a lot of enthusiasm for it, and I knew I’d always need web devs for it. Unless you have worked with someone on previous projects, definitely don’t start out by offering equity. 

  • Balpreet Patil

    keep it up dude.!! wish you very best of luck.!!

    • Jayson

      Thanks very much, Balpreet!

  • NotFan

    Any list of 10 is about the number and not the contents. People don’t think in 10s or work in 10s.

    I see that “making money” wasn’t on the list. The people who worked at crackerize might have wanted to know that. Of course, that’s their responsibility, which is something I’ll get to in a second.

    So we start with Rule #1 for anyone ever involved in a startup: “Know what game you are playing.” In this case, the CEO’s game was to amuse himself, to get some publicity, to build a programmer contact list, and to have a line on his resume that would help him get venture money if and when he ever does get serious about something.

    Rule #2: “Everyone for himself.” People work for their own dreams. If the CEO manages to con them into working for the CEO’s dream, more power to him. But a smart CEO will realize that, in the end, people work for themselves. That knowledge will make it easier to screw your people when the time comes. And trust me, the time always comes in the tech world.

    I’ll come up with more of these if I feel like it.

    • NotFan

      Rule #3: Pay them in common stock, so you can dilute ’em down to nothing later on.

      • NotFan

        Rule #11: Think of Rule #3 after watching the movie “The Social Network”.

    • Jayson

      “Making Money” is another list of 10 in itself, which I could also write about ;) And the list of 10 is a common and effective template to increase readership, since it gives the impression of easy consumability of the content.

      • NotFan

        “gives the impression of”

        I’d say you’re off to a good start in high-tech

  • Gangsta_i_am_not

    Note that none of the lessons is “How to generate revenue”. This is not a startup, it’s a pet project. 

    • Jayson

      “Generating Revenue” is another top 10 list in itself too.

  • Seandr

    Lesson #1 should have been “Come up with a good idea.” If you do that, the rest will fall into place. 

    • NotFan

      How old are you? 19?

      • Quash’qi

        How old are you? 74?

  • maknesiumblog

    A website is a very important part of a startup. I created a useful guide for startup website designers

Job Listings on GeekWork