Rocky, Clubber Lang and How To Get Ready to be a Kick-Ass Entrepreneur



What I learned about the mental side of being an entrepreneur, and how you can apply these lessons and my S.H.A.P.E. formula to your journey.

What was your Favorite Rocky Movie? If you ask me, they were all great – each for a different reason. But I have to admit that I do have a favorite.

Two words: Clubber Lang. That’s right, Rocky III all the way!

If you’re wondering what the hell a Rocky movie has to do with being an entrepreneur, I completely understand.  Hell, I wouldn’t be surprised if a lot of you have never ever seen a Rocky movie.  Some of you weren’t even born when Sylvester Stallone came into fame for his portrayal of the down-on-luck boxer who uses hard work and heart to become a boxing champion.

But bear with me because I’m about to tell you…


First, let me tell you a little about myself. In the summer of 2014, I retired from being a public company CEO. It was a business that I purchased from its founders and ran for nearly 12 years before handing over the reins to a great big company executive to run for me.  Prior to that I worked for two years at a startup called Loudcloud, helping drive business development for Marc Andreessen and Ben Horowitz (now of Andreessen Horowitz fame).

Both of these startups became publicly traded companies and due to this hard work and success, I am fortunate to now essentially be a semi-retired entrepreneur – a pretty cool spot to be at the ripe age of 45.

I’m not bragging or to trying to impress you. It was a difficult journey, on which I learned a lot. Save to say that while the rewards can be great, it is not an understatement to say that being an entrepreneur is a really, really hard road to take.   But the journey is incredibly interesting, complex and emotionally intense – and taking the first step to be an entrepreneur is probably the biggest risk that most of us will ever take.

By most measures, I am very proud of my story.  I took a risk, worked with amazing professionals along the way, learned a ton and am fortunate to have “lived the dream” of jumping into the entrepreneur’s journey and coming out, for most part, a whole lot better than I went in.  I talk a bit about how lucky I have been in my post entitled “Go Luck Yourself” because luck certainly had a lot to do with it.

But there is also more to being an entrepreneur, and my story, than meets the eye.  This leads me right back to Rocky III and the eye of the tiger…

Here is a great summary of the movie plot for those of you who haven’t had the great fortune to watch this cinematic classic, courtesy of IMDB:

“After beating Apollo Creed and become World Heavyweight Champion, Rocky Balboa is enjoying his boxing and top lifestyle, being everyone’s idol. After 10 successful title defenses under his name Rocky believes he has nothing more to prove and is ready to retire. But boxing brawler Clubber Lang becomes the No. 1 contender and demands a match with Rocky for the Title. Rocky has too much pride to reject Lang, and trains for his bout with Lang. Lang brutally beats Rocky, and after the fight, a battered Rocky falls into depression after the death of Manager Micky and does not have the confidence to challenge Lang to a re-match. But Former Champion Apollo Creed is the only man able to persuade Rocky to offer a rematch, and after Lang accepts the challenge, Creed trains Rocky. Rocky must now try to forget about his last brutal bout with Clubber, and try to regain the title and the confidence of everyone, and also try to get back the “eye of the tiger”. Can Balboa win his Title and dignity back?  Written by Mekaeal Chaudary (


The great part of this movie is the hero of the first two Rocky movies gets his butt kicked by an upstart challenger named Clubber Lang (played perfectly by Mr. T).  So what happened to Rocky and what can any entrepreneur learn from it?

In short, Rocky got soft and lost his mental edge. He stopped doing all the things he used to do as a champion and was met with a young up-and-comer who trained harder and was more prepared – mentally and physically– than Rocky. Rocky’s lifestyle was no longer in line with that of a boxing champ, and as a result he got his butt kicked when he stepped into the ring.


My wife still jokes about my apartment back then when she first met me and I was neck deep as a first time CEO chasing my entrepreneurial dream. I had lived in the place for nine months there and my furniture consisted of one chair, a bed and a TV in the bedroom. The apartment was strategically placed at just under a mile from the office so I could get there as early as possible and I could walk back late at night if necessary.

I was 33 and ready to take on the world.

I didn’t own a car, house or dog. I worked 100 hours a week. I flew around the world on a moment’s notice.

I was a working machine – a champion of my job, if you will. I simply didn’t understand anyone who didn’t prioritize job over everything else.  As you can imagine, with an attitude like this I churned through many executives. But we were successful.

We grew the business at almost a 40% CAGR for a decade. We returned over $100mm BACK to our investors even BEFORE we went public. It was a great professional success for me, my team and the investors that backed me along the way.

Fortunately for me, my personal life also prospered during the journey.

I got a dog. I got married. I bought a house. I had a kid, and then three more. I got another dog and another house.


As my professional success increased, I was super lucky to recognize that the personal side of my life had become much more important and much more fulfilling.  Suddenly, I found myself wanting to leave work early to coach T-ball. I didn’t want to fly on the red eye to see a customer or halfway around the world to be with employees.

I was no longer Clubber Lang. I was becoming Rocky at the start of the Rocky 3 movie.

And a new Clubber Lang was waiting (he always is).

My life as Clubber Lang was good to me. It led me to where I am today, and I am quite happy today. But I am thankful that I was able to recognize when I was “done”, which then enabled me to work with my Board to find a great replacement.  In short, I was able to retire before I got my butt 100% kicked.

And now I also realize just how important it is to have the right mindset when heading into the wide open and turbulent seas of being an entrepreneur.  There is so much written about business strategy, building a team and raising capital – all of which are critical to taking your business from idea to the next great thing.

But I would assert that getting yourself ready to take the daily up and downs of running a business, both mental and physical, is equally as important and might have more to do with your success than coming up with a better mousetrap (or Uber).

I stepped out of the proverbial ring when I felt I no longer had the mental edge to keep running 100 mph and now I want to share my learning with you, the next generation of Clubber Lang’s, as you get ready to jump into the ring.


Here is my “unofficial “tips for any entrepreneur, regardless if you are just getting ready to get started or if you are looking in the mirror to see if you have another year (or quarter) in you.  The key, to me, is to keep yourself in SHAPE and take personal and mental health as seriously as you do your business strategy.  Take it from a retired former Champion – staying in SHAPE really does make a difference.

(S) SELF. BE SELFISH. This is the rule of 168. That’s how many hours there are in a week. At least two of those hours should be focused on yourself every week in some form of renewal. Take time away from the job and avoid the temptation to send one more email  Force yourself to find these two hours just for you – not your friends, family or other obligation.  As the old saying goes, you can’t cut a tree with a rusty saw. Find the time to sharpen your saw in a way only you can do.  And not, this isn’t a time for binge drinking or watching House of Cards. Do something productive, such as yoga or meditation. Find your inspiration, sharpen your saw and get refreshed for the road that still lies ahead.

(H) HEALTH. Get in good PHYSICAL shape. Find a way to make this a priority.  Golf, running and walking are all great outlets. Do something that will push your limits and help release some of the stress that you will inevitably feel in the job. This might seem hard when working long hours and traveling, but you have to keep reminding yourself that your physical health is just as important as mental health – you can’t have one without the other.

(A) PLAN. ESTABLISH A WORK / LIFE PLAN. Note: I didn’t say balance, I said plan. The idea of balance is a unicorn. You can’t successfully run high growth business without a lot sacrifice. You can, however, communicate your plan – in whatever form it takes – to your family and executive team so everyone is aware of what to expect from you. Just remember to trust in your plan. When you’re home, don’t feel guilty about not working (and vice versa).   The key here is to be realistic about what you are trying to achieve and to openly communicate the plan to those around you.  For more here watch Nigel Marsh’s funny, inspiring and incredibly helpful Ted Talk entitled “How to Make Work-Life Balance Work”.

(P) PERSPECTIVE. GET SOME. Also get some support and feedback. Find some form of mentorship outside of your company and Board. For me, I was an active member in the Young Presidents Organization (YPO) and sat on two different CEO Roundtables in my particular industry (software).  While these activities seemed at odds with my goals for “work life balance”, in reality both provided me with peer interaction that helped my realize that I wasn’t alone, even though at times the job can make you feel like it.  Connecting with others in the same boat will go a long way toward staying the course – and keeping your sanity in the process.

(E) EGO. Watch it! The trappings of the job can be obvious, regardless of the size of the company you own and manage.  Heck, one of the reasons you probably wanted to be an entrepreneur was to be your own boss, right?  But be careful because the real risks to being “the boss” are more subtle than obvious. There are so many ways you can lose perspective, which is why self-monitoring becomes massively important. Get consistent feedback from somewhere, whether it’s from an external coach or the Board, about how you’re performing along the way. Skip this step and you’ll be surprised at how much you’ll limit yourself.

And for my parting advice: Don’t take yourself or what you are trying to achieve too seriously. I get more than most the importance of giving your all to your business dream off the ground.  It is hard work, time is short and the list of things to do only gets longer and longer every day.

But remember, relatively speaking, we live in an amazing time.  The opportunity to be an entrepreneur and the pace of change and innovation has never been greater.  The “problems” that most of us face pale in comparison with those from just about any other time in history.

So have some fun along the way. You will do great. Channel your inner Rocky or Clubber Lang, get (and keep) yourself in SHAPE and kick some butt!!

Monkey Masters: Jason Dorsey

Monkey Masters: Jason Dorsey

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