How Desperation Caused My First Startup To Fail

Note: This is an update of an article I wrote a few years ago on a blog I shut down.

In 2002, I unsuccessfully attempted to start a digital lifestyle magazine for Black golf enthusiasts called, Seven Under. To this day, when I mention the project to someone, the response I usually get is, “that sounds like an interesting idea, why did it fail?”

It took me several years to come up with the real answer to that question.

The over-simplified answers are:

  1. My partner and I lacked previous publishing experience. We were still novices in terms of having no clue about important aspects like network architecture that play a crucial role for so many enterprises. I vowed never to make this mistake again!
  2. We didn’t have enough money to have a real shot at success.
  3. The timing was bad because Vanguarde Media, which, at that time, was a dominant player in the Black Magazine space, just filed for bankruptcy. And advertisers were not keen on a new publication in the same category.
  4. We were ahead of our time with plans to launch a digital-only version of the magazine in a pre iPad-era.

While there is truth in all those answers, none of them is the real truth. The real reason the magazine failed is because I was too desperate.

final stand alone logo
Failed startup logo

What Is Desperation?

Here’s one of my favorite quotes about desperation:

Desperation is a necessary ingredient to learning anything, or creating anything. Period. If you ain’t desperate at some point, you ain’t interesting. – Jim Carrey

While Jim Carrey is funny, as usual, it’s this next quote that is more relevant to the failure of Seven Under:

Desperation is like stealing from the Mafia: you stand a good chance of attracting the wrong attention. – Douglas Horton

People can smell desperation a mile away and it causes them to run in the opposite direction.

Why So Desperate?

I was a newly minted MBA from the Kenan-Flagler Business School at the University of North Carolina-Chapel Hill and I was ready to take on the world. I would be remiss as a good Tar Heel if I didn’t toss in the requisite chant of, Go To Hell Dook!

But I digress.

While trying to get the magazine off the ground I worked part-time at a 9-hole golf facility in NJ, which paid $10 per hour. I took the job, however, because it gave me a chance to learn the golf business and get to know industry insiders, plus I could meet with potential investors in Manhattan on my days off.

After two years of pouring money into the business, earning very little income, and scores of potential investor rejections, desperation took hold, which, I’m convinced killed any chance of getting the money needed to launch the magazine.

Investors could tell I was desperate and they wanted nothing to do with me or the magazine.

A Lil’ Fun Before Failure

Working on the magazine wasn’t all doom and gloom-I also had lots of fun.

Like the time I appeared on ESPN’s Cold Pizza (Now canceled. Perhaps because of me? Hmmm…).

Then there was the time my partner and I played golf with ESPN anchor, and fellow Tar Heel, Stuart Scott (RIP, Stuart) and his buddy at TPC Avenel and beat them for $20 each; the look on their faces was priceless when I hit a 6 iron close to the hole on a par 3 to win the match!

Prototype Evolution

Here is a very crude mockup of an early prototype with Sir Charles on the cover:


With the help of NBA commentator, Greg Anthony, Barkley agreed to grace the cover of the first issue of the magazine once we launched. I got to know Greg Anthony after I sorta cold-called him. Greg is a real good dude.

The Prototype

Below is an autographed copy of the actual prototype, with Jason Kidd on the cover when he was the point guard of the NJ Nets:

Seven Under
We took 10 copies of the prototype for Jason to sign, he signed 7 and kept 3 for himself. Pretty kewl, huh?

If you look closely, you’ll notice a spelling error (I’m not gonna point it out for you), which, 10 years later still chaps my hide because it somehow occurred after a final proof from the designer.

Key Takeaways

What did I learn from Seven Under that I can apply to my latest startup?

A few things.

    1. No matter how hard things seem I will never, ever, EVER, appear desperate.
    2. The proper way to operate:Like a Duck
    3. According to former Apple evangelist, Guy Kawasaki, real CEOs ship!
      Hmmm, I guess that means I wasn’t a real CEO when I tried to launch Seven Under. Ok. I accept that.

Despite the fact I want WeMontage to be successful almost as much as I want to draw my next breath, you will never know it because…I’m not desperate.

Never. Give. Up.

What lessons have you learned from your failed startup endeavors?

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Feature image credit: Buck epic_fail


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