Tribute to an Entrepreneur

An Unforgettable 50th

I’ve wanted to write this post for a long time.  In fact, I’ve wanted to write it since before I even started this blog.

It started this past September.  I had the good fortune to attend the 50th birthday party of one of my favorite people.  For the sake of this post, we’ll call him “Bill”. Bill is a self-described “serial entrepreneur”.  He was one of the owners of the start-up software company that I started working for in 2006.  At the time I was hired, I was employee #5.  Flash forward to 2012 and we had 120 employees and a thriving business when we were acquired by one of the large, publically traded companies in our industry.  The owners, including Bill, were able to exit and start their next entrepreneurial venture.

Flash forward to September, 2015 (three years after the acquisition of the company I had worked for and nearly 10 years since I first met Bill).  I’m at his house with 40+ of his closest friends and family, celebrating his 50th birthday.  As my wife and I sat outside around Bill’s pool, hanging out under the stars, waiting for the (I kid you not) full-on 4th-of-July-caliber fireworks display launched from his own backyard, I found myself reflecting on a number of different things….

The Slight Edge in Action

First, I found myself reflecting on Bill’s seeming innate ability to create success in all areas of his life.  Keep in mind that back in September, I had not been introduced to The Slight Edge.  So at the time I did not recognize it’s principals in action.  I’ll also make the disclaimer here that I have no idea whether or not Bill has read or even heard of Jeff Olson’s book.  My guess is, probably not.  But for someone like Bill, if he were to read The Slight Edge, he would probably just nod along in agreement at the principals outlined in the book concluding pretty quickly with a “Yep, I get it.” To put it simply, Bill just GETS IT and in my opinion, has things pretty much figured out.

What Bill has figured out that it took me reading The Slight Edge to clue into is the power of the “compound interest” you create through the little things you do every day.  While most of us ride the wave of success and failure, Bill is able to simply stay on the success curve.  And I’m not just simply talking about business or financial success…

Here are just some of the areas of life where I have observed Bill staying on the success curve over the years I have known him.

Health – I’ve witnessed Bill go through a physical transformation through both diet and exercise.  When we first met, he was not someone you would describe as over weight, but I don’t think you would use the word “fit” to describe him either.  However, after this transformation to his diet and exercise habits, he is now extremely fit and has remained so for a several years.  As he was firmly into his routines of eating healthy and exercising, we had the following conversation:

Me: “So Bill, what are your goals when you go to the gym?”
Bill: “Easy…I go to the gym 3 days per week.”
Me: “Yeah, I get that.  But what are your GOALS?  Are you trying to get to a certain weight? Working on isolating particular muscle groups?  You know…what are your goals while you’re there?”
Bill (looking a little puzzled): “My only goal is to make sure I get to the gym 3 days per week.  I know that if I make it to the gym, good things will happen.  I don’t worry about setting specific physical fitness goals which may only serve to frustrate me.  I know that by ensuring that I stick with my commitment to get to the gym 3 days per week, then the fitness part will take care of itself.”

I’ve thought about that conversation a lot over the years.  It makes so much sense but at the time, I was dumbfounded.  I was always an “over-thinker” and thought you had to have these complicated goals and routines in order to get in shape.  And as a result, I frankly was never able to stick with any workout regiment.  But Bill’s response captures the Slight Edge perfectly. Develop a habit that you can stick to for a lifetime and stay on that success curve!

Business – Ok, so this one seems a bit obvious, but yes, the world of business is another area of life where Bill demonstrates his knack for staying on the success curve.  When it comes to business, it is easy to simply look at the numbers of Profit & Loss or what revenue multiple the company sold for.  However, in addition to those measures of success, in my opinion, to be judged a truly successful entrepreneur, I think you also have to look at the culture of the company and the well being of the employees to determine if the business is truly successful.  In short, do people LOVE working for you? Are they HAPPY coming to work? And are they LOYAL to you?  In Bill’s case, the answer is a resounding YES.  Not only is he beloved by his employees, he is revered.  This is no accident.  Again, The Slight Edge is in action.  Bill does the little things each and every day to make his employees feel appreciated and want to work hard for him.  He constantly strives to help employees determine their strengths in order to help them reach their own potentials for success.  He sets a high bar and expects a lot out of his employees, but they constantly rise to the challenge and seem to happily strive for greatness.

Relationships – At his birthday party, it became apparent that not only does Bill have great relationships with his friends and coworkers, but he has phenomenal relationships with his wife and children.  This challenges many of our notions of the driven entrepreneur who burns the candle at both ends for his business, even at the expense of his family relationships.  But not in Bill’s case.  I have never met anyone who is better at drawing that line in the sand and maintain his commitments to his family.  Don’t get me wrong, in a business emergency, he will lead the charge and will do whatever it takes to resolve the issue including pulling an all-nighter with the team.  But he remains equally committed to his family, ensuring they receive both high quantity and high quality time with him.

One of my favorite examples of this is how Bill deals with family vacations.  Most of us struggle with completely unplugging while on vacation.  Whether it’s sneaking a peak here or there at our unread email “just to make sure nothing is blowing up” or dialing into that important conference call “just to listen in“, the fact is that so many of us have a hard time giving ourselves over completely to our vacation and focusing 100% on the people who mean the most to us there.  As hard as this is for most of us, I imagine it is 10 times more difficult for the owner of a business to completely unplug. But again, this is not an issue for Bill.  He knows how important that vacation time is with his family and he is committed to ensuring that every second of his vacation is focused on disconnecting from the business world, focusing on his family and having fun!  In the weeks leading up to his vacation, Bill will ensure that there are others in the organization who can take over all aspects of his job responsibilities.  In other words… he replicates himself.  His ego does not get in the way thinking, “Only I am capable of dealing with this.” He determines everything that would need to happen without him, even in case of an emergency, and ensures members of the team can step up and fill the void while he is gone.  Then, the last thing he does is hands a sealed envelop over to his business partner (the CEO) with all of his important information and passwords.  The meaning of this envelope is simple, “If I DIE while on vacation, you can open this envelope and access anything you need to as it relates to the business.”  And with that, he lets us all know not to try to email him, or call him, or text him.  He will be COMPLETELY UNAVAILABLE and will look forward to seeing all of our smiling faces when he returns.  His family gets 100% of Bill while on vacation – which is really how it should be for all of us.

Personal Development – Last but certainly not least, Bill has mastered applying the Slight Edge to his personal development.  Over the years, I’ve noticed how Bill is always learning and looking for ways to improve.  For starters, he is always staying on top of the latest technologies (he is a technology entrepreneur after all).  When he and his wife determined that they would eventually like to retire in Costa Rica, he started studying and is now fluent in Spanish.  Just this past year, he decided he wanted to learn how to launch fireworks and began working with a local company and participated in a number of municipal 4th of July celebrations.  Bill has embraced the concept of always pushing himself to grow and has developed the habits to keep him on this success curve.  As a result, he knows how to successfully pursue learning whatever new thing he puts his mind to and does so fearlessly and efficiently.

The Impact of Entrepreneurs

In addition to reflecting on Bill’s personal accomplishments, I also sat there thinking about how greatly entrepreneurs impact our lives and how, frankly, we usually don’t THANK them enough for what they do for us.  As I looked around at the attendees of Bill’s 50th birthday party, I realized that at least half of those in attendance were either a current or former employee or the spouse of one of those employees.  Over the years, the number of people who’s lives were impacted by just this one entrepreneur is astounding.  Employees have received checks with Bill’s signature on it.  Those checks have been used for weddings, for buying homes, for raising families, etc.

So think about it…that is just the impact of one business owner.  What about ALL of the entrepreneurs out there?  What has their impact truly been on our lives?  Even most of the larger corporations out there were started at some point by an entrepreneur.  They are the job creators.  What can be more impactful on an individual than the job that was created for them? And those jobs are what lead to so many wonderful aspects of life.  And yet, how often do we thank them?  Are we grateful for the job creators out there or do we take them for granted?

So often, I think we view entrepreneurs as somehow on the edge of society.  We admire their risk-taking and willingness to “put it all on the line” to start a business.  But then what?  I don’t think we realize how important and impactful a role entrepreneurs play in our lives.  And I know we don’t say “Thank you” enough.


All of these thoughts were running through my head during those few minutes under the stars last September.  As the night wore on, people began passing around a microphone and saying all kinds of nice things about Bill.  I wanted to be one of those to get up and speak, but I just simply chickened out. I’ve regretted it ever since.  If I had gotten up, I would have spoken about how much I had learned from him and how I admired him.  And I would have certainly gotten up to thank him and tell him how grateful I am that I too counted myself as one of the lucky ones to have received a paycheck with his signature on it.

In other words, if I had gotten up to speak, I’d like to think I would have delivered something like this post.




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