My History of Failure

“I’ve failed over and over and over again in my life, and that is why I succeed.”

This is my third attempt.  I’ve tried twice before and failed, but this time could be different.  It could end up in failure just like the others, but I don’t think it will.  I’m smarter this time around.  I’ve learned from my mistakes, am better at what I do, and I have more to lose.


The first time around was in 2007.  I had just learned PHP and thought I had what it took to make a video encoding startup.  This was before the term “cloud” was popular, and my idea was that users would upload videos to my service, encode them into whatever format they liked, and then re-download them.  For revenue, I thought that a free service could be done by adding advertising to the beginning of the encoded video.  Or, a user could pay small fee to get moved to the front of the queue and have no advertisements.

The idea seemed good, but I wasn’t dedicated to it.  I got a design going and had the back-end encoding stuff working, but I just couldn’t act on it.  Some other things went wrong too.

  • No motivation – I was still in college, didn’t need the money, and enjoyed my life just where it was.  There wasn’t really a huge motivation for me to do this.
  • No passion – I honestly didn’t care about video encoding.  Sure it’s cool, but only cool from a technical standpoint.  It wasn’t something I could really get behind.
  • Knowledge – I really had no idea how deep the programming rabbit hole went at this point.  Not knowing what good design was really put a cramp in how fast I could develop too.  In short, I was inexperienced and it showed.
  • Flawed business model – In retrospect, this should have been a freemium model.  10 minute video for free, anything over is charged.  That way people don’t get annoying advertisements added to their videos.

Should I Get The Book?

In 2008 and early 2009 I worked on “Should I Get The Book?”(SIGTB).  As a grad student reflecting on my undergraduate years, I realized that I spent a ridiculous amount of money on books that I never needed.  After talking to friends and classmates, it seemed this was a universal problem, and my startup idea was born.  This time, I did things right (sort of).  I took a few hours every week over the the summer and started hacking away at it.  By the end of the summer, I had a functioning product.  I did a launch, and the waited.  But nobody came.

So what happened?  Was it competition?  Was it a poor idea?  Well, it was a lot of things.

  • Design – This is huge.  My site design sucked.  I basically ripped off a WordPress template that somebody made because it looked cool.  It had nothing to do with my idea, and it showed.  People coming to the page would say “So what is this about?”.
  • UI – The interface and experience was awful.  None of it made sense, and the changes that people did suggest I back-burnered until I “had more time”.
  • Seed Data – The idea that users leave reviews about whether they needed the book or not was great, except that nobody would do it.  Without having some reviews already in there, I found that people weren’t motivated to leave a review because they thought the site wasn’t being used.  I needed to have data seeded, but I couldn’t think of a good way to do this without paying any money (I had none at the time).
  • Focus – I tried to focus on too many schools at once with the first launch.  I should have started with one to see if the concept would stick.
  • Advertising – On a college campus, flyers and word of mouth is key.  I had zero flyers and nobody talking about me.
  • Karma – Users like getting a reward for doing something.  It doesn’t have to be money, karma works just as well.  Users get to scratch their competitive urge by posting reviews, getting karma, and checking to see if they have more then their friends. I should have done this, but didn’t.
  • Evergreen data – One of the big problems with this data is that the instructor can change books, change styles, or even stop teaching.  The data can become useless quickly.

Once I realized most of these things I vowed to start a re-design with all of these issues addressed.  I was about 25% of the way through the mock-up when I was informed that had a similar feature.  It was easy to use, and they already had a huge user base.  My idea was basically sunk.

While SIGTB flopped, it was important step for me.  I had pushed a project through to completion, learned a lot about marketing, and learned that I really need a co-founder to talk me out of bad ideas.  Most importantly though, I proved to myself that I could accomplish something.  I might have given up too quickly, but I think that the idea wouldn’t have worked well anyways.

CampaignAlytics (Working Name)

I started this idea out in late October of this year.  The idea is that email campaign analytics can be done better.  Currently analytics is rolled in as a feature for big mailers (Mail Chimp, etc), but it doesn’t provide the in-depth analytics that a lot of marketing folks are looking for.  We’re looking to change that.  I’ve been working for an hour a day since November 1st, and have a lot to show for it.  I pitched the idea to a local pitch night, and the reception was great.  We have a lot of great features, and do it all in a non-obtrusive way that is compatible with mailing services, or can be rolled into your custom solution using our API.

I’m taking a different path with this startup, based on the things I’ve learned on the last two.

  • Pay for a design – The first thing I did for this web app was pay for a design.  I got a great deal, and now have a design that I can be proud of and shows off the product like nothing I could have ever come up with.
  • Co-Founder – Having someone to talk you out of bad ideas, and give you a sense of perspective is amazing.  Having someone to discuss ideas with and share the burden is pretty great too.
  • Funding – I’ve come to the conclusion that without a little bit of funding, this startup will take forever to complete.  We’re applying to the seed incubator Momentum and hopefully we’ll get funded.
  • Iterate – I’ve already gone through two different layouts and menu structures for the account/analytics page.  The second version is far better than the first because I asked for feedback from a few trusted people and implemented the changes right away.

The thing I hope you can take away from this is that you are going to fail many times before you succeed.  Being persistent (and maybe a bit stubborn) will take you 70% of the way there, and the rest is on how good your idea is.

By Jack Slingerland

Founder of Working and living in Raleigh, NC. I manage a team of software engineers and work in Python, Django, TypeScript, Node.js, React+Redux, Angular, and PHP. I enjoy hanging out with my wife and son, lifting weights, and advancing in my free time.

6 replies on “My History of Failure”

Success is failure turned inside out, the silver tint in the clouds of doubt.

You never give up and you never give in.

The only difference between you and the 10,000 other clones out there is the time it will take to burn through millions in investment. Even Sorenson’s new “encode in the Cloud” offering is doomed to failure.

About 75% of video encoding is creating the perfect source. That involves hundreds of possible options that can’t be automatically determined. Sending the file through the codec(s) is the last step. Yes, it can be automated, but who cares?


Thanks for putting this out there, its awesome to see the history behind a start up and knowing it’s not the first idea. Most startups that succeed are 3rd/4th tries. So hopefully this one will be your success story!

Am I to understand that you do have a co-founder? Is he/she a developer as well?

Looking forward to seeing you next weekend.

Yeah, I do have a co-founder. He lives up in Midland, so we’ll see how everything works out.

He has a Computer Science degree, and a M.S. in Information Systems, but I wouldn’t call him a developer. His strong points are his business skills and selling skills. He could sell a blind man a painting, which is a very good thing in the startup arena.

Do you have any ideas you want to pitch next weekend or are you going to help build/create like I am?

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