The 5 Stages of Entrepreneurship: What Stage Are You?

The journey of an entrepreneur is a long and winding road. It’s a test of endurance and one’s ability to evolve and adapt.  I’ve always been one to observe processes and try to break them down. Looking at both my personal journey that is just beginning and those that are far ahead of me, I’d like to share my thoughts on what the major steps are in becoming a successful entrepreneur. And while we’re talking about the process of becoming one of the greatest entrepreneurs of all time, it's only appropriate to quote lyrics from one of the greatest rappers of all time, the Notorious BIG.


The 5 Stages of Entrepreneurship

1) The Awestruck Amateur

It was all a dream
I used to read Word Up magazine
Salt'n'Pepa and Heavy D up in the limousine
Hangin' pictures on my wall

When I first caught the bug of entrepreneurship, I found myself in awe: Richard Branson flying around the world in a hot air balloon while he builds the Virgin Empire, Mark Cuban running the Mavericks and numerous other ventures and Steve Jobs changing the world, one new consumer electronics product at a time.  

It all seem so magical; the kinds of people that start and build great companies are these larger than life legends that must have been born with super powers.  And while you feel like it’s impossible to be like them, you’re strangely drawn to it, wanting to somehow find a way to become one of them.

This idolizing hit me during my freshman year in college. As I dug deeper and deeper into startup mythos throughout my undergraduate career, I found myself more and more excited by the principles and feeling less and less like it was an impossibility for me to do it too.  Getting to this point lead me to the next step…


2) The Delusional Dreamer

Biggie Biggie Biggie can't you see
Sometimes your words just hypnotize me
And I just love your flashy ways
Guess that's why they broke, and you're so paid

After hearing the 100th entrepreneur speak about it and reading more books, Inc Magazine articles and blog posts than I can count, I finally was believing it: “You can do it too.”  So I set out to start something myself.

Ignorance is bliss.  At this stage, you think you can conquer the world, but you have no idea what you’re up against.  You’re imagining your millions in revenue, but you don’t even know how you’re going to build or market your product. At this point, I didn’t even know what made a startup “real” versus still just a project; I still remember the puzzled look of my professor when I asked what made a startup “real.”

This stage is the most dangerous stage of entrepreneurship. As a Delusional Dreamer, you can get in seriously over your head as you get so distracted by any early success, without developing an appreciation or understanding of what you’re really up against.   You may think you have the best idea in the world for a startup, but you don't yet realize how little that matters compared to execution.

Unfortunately, there are no easy answers to surviving this stage. You get your first (of many) startup scars and it’s only in making painful mistakes that you learn the greatest lessons.  However, as you collect those early scars, you’ll start learning to anticipate and avoid some of them, which leads you to become...


3) The Battle Hardened Realist

I don't wanna live no mo'
Sometimes I hear death knocking in my front do'
I'm living everyday like a hustle
Another drug to juggle, another day another struggle

Startups are not all sunshine and rainbows. If you make it this far, you’ll know this firsthand. Maybe your first idea failed or you were lucky enough to take these hits early enough you’re more intelligently pursuing your startup.  Either way, your world has grown; you now realize that the amount you have learned and have under control is vastly smaller than the amount of knowledge you so desperately need to succeed.

The key skills to surviving this stage are taking the initial enthusiasm and passion from the first stage and applying it to an undying hunger for learning and finding ways to surround yourself with people smarter than yourself.   It is through the help of mentors, self education and pure desire that you’ll survive the journey and start building something great.


4) The Humbitious Master

It's like the more money we come across
The more problems we see

Humbition is a subtle blend of humility and ambition that drives the most successful leaders; it’s the understanding that you can’t do it all yourself. With the help of others you believe you can make anything happen.  The key difference between this stage and the one before is experience and success; you can learn a lot from failure, but nothing compares to the lessons learned from learning what works.

Everything gets easier after the first time, especially if you're building on success. The Humbitious Master understands that victories of the past do not guarantee future triumphs, but with the lessons learned as a Battle Hardened Realist, you're surrounded by others who can help place the odds in your favor.


5) The Wise Sage

I been in this game for years, it made me a animal
It's rules to this sh*t, I wrote me a manual
A step by step booklet for you to get
your game on track, not your wig pushed back

Few entrepreneurs ever reach this stage.  Some have early success and so never experience the scars that train an entrepreneur to appreciate the journey (and thus become misguided and cocky), while others give up before ever reaching this deep of an understanding of the life of a great entrepreneur. For those that do make it, the rewards are plentiful and deeply fulfilling.

You've been there and done that. You've got your scars and realize what's hype and what's not. You've gone soup to nuts on launch through exit at least once and watch with eagerness as others set out on the journey.  You’re hardened by the experience and are now helping give back.  You’re most helpful to those heading into or working through the third stage as they are most looking for assistance and need the most help that you can directly provide (i.e.- experience).

The beauty of this stage is that you’ve likely realized there’s still more to learn and are still working on new ideas.  When I think of the Wise Sage, I think there are many in our community that fit it, but few are better than Dharmesh Shah. He’s constantly dispensing wisdom in his presentatins, his blog posts and tweets, while also building yet another great company in HubSpot.  We should all aspire to make it here.

Intimidated? You should be.

But don't let that stop you. It's a journey every great entrepreneur has gone through and even if you’re just getting started, understand you have an exciting and fulfilling ride ahead of you.  And if you’re looking for some inspiration, just remember:

Sky is the limit and you know that you keep on
Just keep on pressin on
Sky is the limit and you know that you can have
what you want, be what you want, have what you want, be what you want


Special thanks to Wayne Chang (his blog), Josh Bob (his blog) and Jason Baptiste (his blog) for their feedback and help editing this post!


Photo Credit: tibchris on Flickr




Great job Jason!! You have

Great job Jason!!

You have explained the points very well..much appreciated work.


Roger James Hamilton

biggie biggie give me one more chance!

great read with the biggie references!! super fun

Sidi Gomes


Thanks for reading, Sidi.

 Good luck in the journey through the stages!



Jason Evanish
CEO / Co-Founder
Greenhorn Connect
Twitter: @Evanish