Wednesday, September 30, 2009

Entrepreneurs – A Long Distance Dedication

For my Musings-in-a-Minute version of “Entrepreneurs – A Long Distance Dedication”, please click here.

I have been blessed to have been an entrepreneur for many years and many of my dearest friends are entrepreneurs.

When we get together we laugh, swear and weep over the world that we live in, a world that can only be appreciated by a fellow entrepreneur.

As we used to joke years ago in the software company that I co founded in New York - “Some day we will look back on this day and nervously change the subject” – and then we would laugh.

For any of you not familiar with Kasey Kasem and his long distance dedications, people in one part of the world would write a letter to Kasey that was directed towards a friend, parent, lost-love or some other person of importance.  Kasey would read this long distance dedication and would then play a requested song.

Before I send Kasey my long distance dedication, I would like to share some thoughts about the entrepreneurial world.  If you are an entrepreneur, you will identify with many of these.  If you are not, it will either entice you to join us or frighten you away.  :-)

As I think about the world of entrepreneurs, and speaking from one entrepreneur to another, do you remember when:

1. You were first seized by an idea that seemed ready to take on the world but no one else agreed?

You went ahead and followed your dream anyway.

2. You weren’t the first to come up with an idea but once you saw the potential of someone else’s idea, you were more passionate than the people who came up with the idea.

You stepped around their fear of “going for it” and created a dream.  Some may have accused you of stealing it, but they never had the guts to go for it anyway.

3. You struggled with balancing family and work, recognizing that both deserved 100% of your time.

You did your best to balance both, second-guessing yourself the whole way - “maybe I could have done ______ better”.  Some of you couldn’t balance both and one of them died.

4. You stood on your deck at 2:00 in the morning, looked up at the stars and asked the Universe for help with __________.  Maybe you wept as you did it.  Maybe you made heavy promises if favors were granted.  Maybe you sold your soul in exchange for success.

You look back at those moments now and remember them as pivotal moments, either taking you closer to success or convincing yourself that it was time to get out.

5. You spoke incessantly about your idea to everyone who would listen to you, like that first boyfriend or girlfriend years ago that the rest of us got tired of hearing about.

Your passion either branded you as crazy or inspirational. You didn’t really care because you knew that the people who matter cared for you and supported you, even if you were insane.

6. You wondered where the next payroll was coming from and lost many nights of sleep over it or perhaps chewed your fingernails off thinking about it.

You dug deep and pulled it from your personal line of credit, your friends, an investment round that closed at the 11th hour or by some other stroke of luck or brilliance.  You swear this will never happen again but for some reason, it does anyway.

7. You wanted to share your mental load with your team but you felt it would freak them out and so you shouldered the burden alone and in silence.

If you never got pushed right to the edge, it is a secret that is going with you to your grave.  If you did get pushed to the edge, you surprised yourself with your ability to write powerful, emotion-filled, transparent emails that really helped people understand the pressure you face as a leader.  Maybe you rallied around this and saved the day together.

8. You wanted to be a rah-rah guy but discovered that sometimes you have to make tough decisions that you fret about.

The decisions that you thought would ruin someone else’s life often turned out to be blessings in disguise for everyone and everything worked out in the end.  As Mark Twain once said (paraphrasing) – “I have discovered that most of the worst things in my life never happened”.

9. You wanted to offer more rewards to your team but the budget didn’t allow for what you thought they deserved.

You created what started out as small things that evolved into legendary corporate practices that people speak lovingly of as in “I was there when we created ______”.

10. You doubted yourself the whole way, wondering if you were good enough, smart enough, connected enough, passionate enough or had an idea that was good enough as you faced bankers, investors, customers and future employees.

The person on the other end of that conversation was wondering the same thing about themselves – you just didn’t know it.

11. You wanted or needed some high-priced talent to give you client contacts or credibility but you couldn’t afford them (or so you thought).

You ended up crafting a deal that worked for everyone and helped your company move closer to success.

12. Your creation felt like a living, breathing entity because that’s what it was to you.  If you heard me talking with my team over lunch, you would have assumed that we were talking lovingly about a member of the team and not “just” a piece of software.

13. You wondered why no one else had your passion to just throw worry to the wind and go for the big dream.

Maturity that came later taught you that not everyone is cut out to be an entrepreneur, even though it seems the most obvious and fulfilling thing in the world to be from your perspective.

14. You thought you knew it all but discovered quickly that you were indeed the student and not the master.

15. The person you met for coffee envied you and the life you lived as “your own person”.

As they heaped praise on you, your mind wandered to five customer proposals that needed to be done by Friday, two investor dinners next week, your son or daughter’s upcoming school play, three performance reviews that need to be done in the next week, etc. etc. etc. and you think – would you REALLY want my job?

And then you think – would I REALLY want to be doing anything else?

No way.  This is where you are meant to be.

This is how your passions come alive.  This is an expression and extension of you.

Of course, these things apply to the entrepreneur who eventually made their dream a success.

What about the ones that didn’t?

If you didn’t make your current dream a success, you didn’t fail.  You were merely offered an extraordinary set of life lessons.

The key lesson if you didn’t succeed the first time is:

Will  you get back up and try again?

Because in the end, that’s the real lesson of entrepreneurship.

Despite everything you will learn about networking, financing, execution, business plan writing, exit strategies, negotiation, IPOs, mergers and acquisitions, HR rules, real estate, contracts, pipelines, lead generation, deal closing, reports and everything else, the real question is:

How badly do you want your purpose and passion to be fulfilled?

So my letter to Kasey Kasem would read:

Harry writes:

Dear Kasey.

I am a chronic entrepreneur who is sending words of support to all other entrepreneurs.  For the great obstacles they will either step over, around, go under or learn that they need to be doing something else, the world of the entrepreneur is filled with the greatest rewards.

They create friendships that last a lifetime.  Friends like RL, CDT, MdC, JP, NN and others will live in my heart forever.

Being an entrepreneur allows your purpose and your passion to manifest – to provide an opportunity for you to have a lasting impact on others.  It helps define your legacy – that marker that says “I was here”.

Being an entrepreneur is rarely easy.  In fact, many times it will knock you to your knees.  But we get back up, learn from our challenges and move forward.

In the end, we always win.  Sometimes the victory is obvious.  Sometimes, the lessons are not obvious until much later.

So, Kasey, for fantastic entrepreneurs out there, people like MP, AG, BJ, KC, MB, RM, HJ, GP, MC and all the other people who dare allow their purpose and passion to fly, could  you please play “Don’t Stop Believin” by Journey?

Most sincerely,


Ok, Harry, here’s your long distance dedication.

To the entrepreneurs I have served with, I thank you – you have blessed my life tremendously and I owe you a lifetime of gratitude.  The lessons we have learned together are deep, broad and rich.

To all entrepreneurs, you are closer to your dreams than you realize. 

It all comes down to how badly you want it and what are you willing to do to make your dreams come true?

In service and servanthood.


PS I would be remiss in my duties if I neglected to write about the importance of family and friends.  While you may think that others don’t understand the world of entrepreneurs, they know more than you realize and they care more than you know.  One of the greatest lessons I learned despite all of my so-called confidence in my own abilities was the ability to be able to ask for help when I needed it and to be open to receiving help.  I have my friend Leonard to thank for this lesson.  When all is said and done, humility may carry you further than confidence.

In addition, if you are a person of faith, hold onto it, however you define it.  It will be an incredibly powerful, guiding, nurturing light when darkness seems all around you.

For my Musings-in-a-Minute version of “Entrepreneurs – A Long Distance Dedication”, please click here.


  1. Well - I am only halfway down this small to deal with some of the big issues down the road. It certainly hits home so far though!


    Liz from

  2. Harry,

    Thank you! Again in an hour when I was contemplating walking away with battle scars you helped me realize that there was a reason I started my vision, a reason why the long nights with no pay and loads of frustration are all worth the effort of living my passion, my dream.

    Thank you for your support, encouragement and alignment.

    Living the life of an entrepreneur is not easy but as you said very rewarding even with the choices that teeter on insanity.

    I look forward to the day we meet and have time to sit and talk about the importance of authenticity in life. I appreciate and cherish our long distance friendship and I thank God that we have connected for a greater purpose.

    Peter Jarmics

  3. Though not everyone is an entrepeneur, I believe everyone of a certain age or older knows one, lives ith one or is related to one. As someone who is married to one, I want you to know that this was a beautiful piece and a great reminder to the entrepeneurs of all they have going for them. It's also nice for the support team to be reminded that this is the passion of someone who you love and whether you are in love with the dream, you are in love with the person who the dream starts with.

    Thanks again for a great thought provoking article.

  4. Hey Liz,

    Welcome to the blessing and the curse of having the entrepreneur bug.

    I hope you enjoy the experience. :-) I know for me, in good times and in bad, it has created memories and friendships that I express gratitude for every day!

    Take care and create a great day!


  5. Hey Peter,

    You are very welcome. Thank you for your kind comments.

    It seems like an interesting coincidence that every time I feel REALLY moved to write something, it seems to really resonate with people.

    When I write my blog, I feel compelled to write it - not just write it because it's fun, appropriate or whatever. I HAVE to write it.

    I don't believe in coincidences. I wonder if, when such a mood hits me, if the Spirit calls upon me to write because someone else in the world would like to hear the message at that moment.

    I am very much looking forward to having the face-to-face conversation with you, Peter. :-)

    Thank you again for your service, for your spirit as an entrepreneur and for your support as a friend.

    Take care and create a great day!


  6. Dear Anonymous,

    I was very moved by your comment.

    The family component of the entrepreneurial world is a very important component.

    Entrepreneurs sometimes get so caught up in stuff that they don't realize the great support they get from their family.

    The families sometimes don't realize how important the dream of the entrepreneur is and how much support they need - ESPECIALLY when they are not asking for support.

    When communication is strong, the mutual support can be so powerful.

    Thank you for the wonderful note.

    Take care and create a great day!


  7. Harry,
    Your article came at the right time. I was putting together a book campaign for my book when it is released next month. I felt overwhelmed with all that had to be done but then your email came. I related to many of your bullet points about entrepreneurs and felt a kinship to those who take risks and are prepared to pay the price to make them come true. Not only do we have to create and energize but we also have to know when to ask for help and when to offer it. Your many lessons inspire me to take an even bigger leap into life. After all, we only have NOW!

  8. Dear Leonard,

    As an author, you represent a special type of entrepreneur where the rewards are truly unknown until after your work has been put out there.

    It is also special because in the field you are in, your writing exposes more of your inner heart than another type of entrepreneur (say ... a software consultant). And so with everything else on the line, you have the additional complexity of being more "naked" to the world than many.

    Asking for help has been one of my greatest lessons. My greatest reward would be the incredible relationships I have made. They will last beyond any other impact I have made and are by far, the pot of gold of more value than money.

    The time is indeed NOW - that should be the rallying cry for every entrepreneur.

    Thank you for your kind note, Leonard.

    Take care and create a great day!


  9. Thank you Harry,

    It is funny how intuition and spirituality have become important guideposts in entrepreneurial journeys, as you allude to.

    Looking back (I do that a lot) I can see a distinct trend that differentiates my entrepreneurial successes from failures.

    Successful ventures, in their early days seem characterized by serendipidous events, enabling relationships, coincidental outcomes; like paddling downstream, or like a helping hand reaching down to remove obstacles. Not so much luck I would say, as awareness of these things.

    Looking retrospectively on my more difficult experiences, there were clear signs when things started to clogg up, when trust seemed to fade, the team slipping into misalignment.

    These are now evident to me as trigger moments for an intervention of some kind to get the venture back on track. I recall such efforts in the past but they were rather ham-handed, as trust was already fading.

    What an effective intervention looks like would be an interesting exercise to explore and it would not surprise me if your experiences have created such an instrument, perhaps something like a mirror to hold up to the team, or revealed light.

    Looking forward to more postings from you as this is the first one I have read.

    So thanks again,


  10. Hi Henry,

    Thank you for your kind response and your insightful comments.

    I agree 100% with your observations.

    I have felt over the years when I look back (and I do that a lot also!) that at times when I lost trust and faith that things would work out, then I would begin to scramble to force a desired outcome.

    This effort to force a desired outcome pretty much guaranteed at best, a jumbled, overcomplicated effort and at worst, a catastrophic failure. It also didn't allow me to develop the skill of trust.

    Over the years, with experience and the guidance of wonderful friends and mentors, I have come to trust that good people who:

    - have good intentions
    - have smart execution
    - are humble enough to admit they don't have all the answers and that they welcome help
    - share or give away the credit as opposed to owning it
    - give to their network more than they take from it
    - have faith when the bombs are falling all around them

    tend to be more successful and pull some amazing feats of snatching victory from the jaws of defeat.

    As Paulo Coelho wrote, warriors (which includes entrepreneurs) show courage in the face of challenge, show detachment (thus allowing them to focus on the outcome and not the noise around them) and show a touch of madness in keeping their hope alive when everyone else thinks it is insane to move forward.

    It is not an easy journey but it sure creates a life rich in experience.

    When people ask me how I have accumulated so many stories in my lifetime, it is because, I believe, that I have put myself out there to experience life.

    It's not always easy .... but oh, the richness of the experience.

    Thanks for your kind thoughts, Henry.

    Take care,