How Much Pain is Required for Entrepreneurial Success?

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There was a program available on Netflix instant streaming called Global Business People. Each episode profiled three individuals, mostly entrepreneurs and some top executives, who had reached the top of their industry or craft. For several weeks, I studied those profiled and an interesting pattern emerged. Not only is pain a prerequisite for entrepreneurial success, but extreme pain and in steady doses.

photo credit: Silvia Sala

photo credit: Silvia Sala

How far are you willing to go and what are you willing to give up?

The most amazing profile was that of Cathy Hughes. In the late 70s, Cathy was a lecturer in the communications department at Howard University. She later became the station manager of the university’s radio station. In 1979, she bought an AM radio station with her husband. The sky fell a year later when she and her husband split up and she lost her home.

I suspect this disaster would be enough for most of us to cry uncle, but Cathy moved into the studio with her young son and they slept on the floor in sleeping bags. The station remained in a financial hole for 7 years.

In today’s “lean” culture, how many of us would hold on to such a failure for 7 years?

As the station began moving into the black, Cathy took this as an opportunity to seek outside capital. She pitched to 32 loan officers. The first 31, all men, turned her down flat. One even had the audacity to ask if her husband was part of the business.

By the time Cathy delivered pitch number 32 to a female bank manager, she was on autopilot. Part way through the presentation, the bank manager agreed to give Cathy a loan. Instead of stopping to celebrate, Cathy continued with her presentation. Not to over sell but because she did not hear the news. The bank manager interrupted Cathy a second time to deliver the good news.

Today, Radio One has 53 stations with revenues in 2012 of over $400 million.

For those who think her son was deprived because of his mother’s obsession, that kid would later go off to UCLA and return home with an MBA. He helped take Radio One public in 1998.

The Rule, Not the Exception

Cathy’s case may sound extreme, but it is more of a rule than an exception. If space allowed, I could give dozens more examples. So, instead here are the distinct traits I noticed in most of the individuals profiled.

1. No plan B – For this group, plan B is a distraction to plan A. Exit strategy? Success. If they fail, they try all over again until they get it right.

2. A willingness to give up “shiny things” – Shiny things includes more than physical possessions, but also reputation and community standing. Can you imagine the embarrassment of losing your home in a business venture and having to explain this to friends, family and former colleagues? Then, explaining why you still believe in that business 7 years later?

3. An Obsession – We talked about this before in my article “What’s Luck Got to do With It?” but I cannot find a more suitable word to describe this group. In preparing for this article, I am more convinced than ever that obsession is a key ingredient to reach this level of success.

4. Delusional – …Until they hit it big of course. Then, we call them geniuses. These folks are willing to accept ridicule from those closest to them. Most people cannot endure this type of pain and simply dabble around the edges in order to remain acceptable to their peers. While others run from discomfort, they take it as a sign of a breakthrough.

Do you believe the above 4 traits are requirements to reach this level of achievement or is there an easier, less risky way?

How far would you go?

Godspeed and I look forward to seeing you in The Players Lounge.

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Derrick Jones
Derrick Jones is a former Marine, serial entrepreneur of three tech start-ups and author of "Presidents, Pilots & Entrepreneurs - Lessons from the Trenches for the Everyday Entrepreneur." In his book, he chronicles what he calls the good, the bad and the ugly of entrepreneurship with key lessons for beginning entrepreneurs. He is a regular speaker at schools and trade organization on the subjects of entrepreneurship, leadership and technology. He mentors aspiring entrepreneurs on his own time and through his volunteer work with SCORE. He also shares his experiences on his blog
Derrick Jones


Serial Entrepreneur & Author of Presidents, Pilots & ENTREPRENEURS
@ReginaJinglesNY Yep. Been too busy. Lots of flying. Will b back soon more regularly. - 1 month ago
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  1. James Oliver, Jr. says:

    Dude, when I saw the title of the post I only thought of one thing, which sums it all up. See video below: [youtube lSPNQ82Sq4E youtube]

  2. Gettysburg Gerry says:

    Derrick, I can so resonate with this post, excellent, reminds me of the video Pain is Temporary by Eric Thomas…Great job..

    • djoneslucid says:

      Thanks Gerry. The tricky part with "temporary" is one an never know how long that is. Even to this day, Cathy Hughes says she never considered quitting, even in her darkest moments. I didn't mention this part in my article, but she would say to lenders, "Do you think I'm going to let this thing fail with me sleeping on the floor of the studio?" Wow.

  3. I worked for a company that failed, but we turned everything around re-branded and started a new company that is now very successful. What I can say is most of my friends thought I was crazy working for over a year not getting paid a dime. Many of them said they knew my company would fail but I didn't really care much as to what they thought. My reason? I knew they weren't close to my business. They had no idea what was going on so how could they know if it would fail or not? While they were ultimately right about that particular business failing, they were actually very wrong as to the reasons of why they thought it did (shows how much they know) and Im sure that other people in my position think the same thing about what their friends have to say……Anyway's today I'm sitting in a better spot than all my friends and I wouldn't be here if it wasn't for that original business I decided to take a chance on!

    • James Oliver, Jr. says:

      That's awesome. I recently read something that sorta said, "entrepreneurs do the things today that others won't, so they can do the things tomorrow that others can't."

      Great story.

    • djoneslucid says:

      And most of those naysayers will quietly wonder "what if?" in their old age. Good for you.

  4. I don't agree with #1, but apart from that, I say: Bang on! You have to have a plan B if you really want to succeed — even if this second plan follows pretty much the same pattern. Sometimes, you need to change your outlook slightly to start seeing results.

    Interesting case study! Thank you!

  5. I love the "Extreme pain and in steady doses" LOL yup experienced that today. People not meeting deadlines can't get my product ( I invented) shipped on time to get samples so now it's pushed back about a month. People waiting on their training video ( I coach too) and my baby crying ( teething). It was quite the Mompreneur day over here. Steady pain – true that my friend true that.

    • djoneslucid says:

      Well Lisa, just like in the gym, if you are experiencing that much pain, then a breakthrough is just around the corner. I am sending you a virtual high five! Mompreneurs are the real deal.

  6. I agree particularly with #1 and #3. To start a company or achieve any lofty goal, you have to be obsessed–you have to give it your all with no distractions, no exit strategy, no "other option."

    • djoneslucid says:

      Thanks for the comment Jeremy. The obsession thing is a real sticking point for many people because the word has such a negative connotation. But it does seem to be a common trait amongst the ultra successful.

  7. One important quality that a successful entrepreneur possess is to keep up with the similar project whatever it takes to stick to it which makes him stand out as in case of Cathy after that disaster too, she stood up with her own studio and after all the efforts and hard work she has managed to make her radio station rule today having 53 stations from that one.
    Thanks for the post.

  8. Marius Fermi says:

    When I see these posts it gives me that extra bit of hope – I'm working with a company, could call it a startup, where we are chasing aggressive growth. My incentive is shares in the business at the end of the year so basically everything has now come to a stop.

    I work 12-15 hours daily, try to have at least half a day off once during the week, given up with TV, Xbox etc and basically say no to the majority of things I'm asked to go too.

    Focus and friends/family that appreciate your hustle are what you truly need.

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