Arment Dietrich

The Three Stages of the Entrepreneurial Mind

By: Arment Dietrich | April 27, 2011 | 

During the past five years, I’ve had the opportunity to work directly under someone (cough, Gini Dietrich) as she has evolved through each of the following entrepreneurial minds.

I’ve now come to a point where I think I’ve figured out how these minds work.  Yes, they say it’s lonely at the top for this select group of individuals, but because they move too fast for the rest of us to keep up, the loneliness is self-inflicted.

I’ve created a chart outlining the stages of an entrepreneurial mind to help the rest of us make it less lonely for our beloved CEOs.

It’s not as National Geographic as I thought it would be. In fact, it’s pretty simple.  Your own CEO is probably at one of these stages now.

Stage One: Mountain Top Envy

We all do this; we want what we don’t have.  But the difference is most entrepreneurs will do almost anything to get there.

Stage Two: I’m Lonely and Scared of Falling

Here is where you’ve reached the destination but you know that one wrong move might shake the rest of the foundation.

Stage Three: Conquered Mountain, Now On to the Next

Now that you have your footing and are confident, you see the next challenge and start deciding how you’re going to get there.

So what does this mean for those of us who work for these entrepreneurs?  Well, if you can take a step back and see which stage you are in, you can determine where the responsibility lies and when it’s time to make your move.

I’ll give you my example of Arment Dietrich, Spin Sucks, and Spin Sucks Pro:

Arment Dietrich was in stage one when we decided we wanted to create a leading PR industry blog.  We started Spin Sucks, learned a lot, and got where we wanted to be. Then, Gini decided she wanted to tackle the next mountain, and along comes Spin Sucks Pro.

I watched my CEO go through the stages and am able to recognize where opportunity is calling my name.

As any company enters phase three there are roles employees can play:

  1. Once you see your CEO/company sitting nicely at the top of the mountain now is your time to strike!  If you’ve been holding on to a great idea that you want to embark on, share it now!
  2. If your CEO is moving into phase three decide if now is the time to step up and let your boss know that he/she can trust you to take over management of that mountain while they pursue the next.
  3. OR, let your CEO know that you want to be their right-hand man on that next mountain climb.

In my case, I decided I wanted to go with option number two.  I let my CEO know that she can move onto Spin Sucks Pro as I help manage Arment Dietrich.  It is up to us to step up so we let our CEOs use their minds the way nature intended.

Is your company in one of these stages now?  Do you see an opportunity calling your name?

  • rustyspeidel

    What did she say?

  • Pingback: The Three Stages of the Entrepreneurial Mind : Business, Jobs, Microsoft Code, Startups, Open Innovation (…)()

  • Great drawing 🙂 …ok, maybe not, but a great point. Congrats on holding the fort down while Gini concurs her next Everest.

    Im looking fwd to more insightful posts from the mind of Molli 🙂

  • MichaelDurwin

    I thought this was going to be:1) Excited by the new idea2) determined to make it happen

    3) deeply hateful at not getting funded


    3) relieved to get funding

    4) overwhelmed by feature creep

    5) nervous about adoption

    6) elated at explosive growth

    7) confused as to why your board just fired you as CEO

    8) depressed by the hand cramp from filing out applications for Starbucks

  • bdorman264

    All I know is you have a great name; you can be the lead in the female version of “Being John Malkovich”. It just rolls off the tongue well, can I borrow it sometime?

    Ah, keeping up with Ms Gini is challenge all by itself; knowing when to step in and contribute when it’s needed most is probably an art, and it appears you have figured it out.

    There is no ‘i’ in team, right.

  • MolliMegasko

    @bdorman264 Being Molli Megasko does have a nice ring to it.

  • MSGiro

    Molli I think you’re being too nice. Not nice to Gini or Gino or whatever the heck auto-correct chooses for her name, but rather to entrepreneurs as a whole. We aren’t “nice” people. Before an entrepreneur, which I am a member of that club, worries about mountains and falling and whatnot we deal with the creation of a defense mechanism to our arch enemy NO. It’s the word we hear the most and it comes from all over; friends, family, customers, vendors, hot dog vendors, random internet haberdashers who make stupid comments on blogs.

    Once we develop the immunity, which includes a serious amount of soul searching tied to self-doubt, we create an absolutely maniacal personality that will destroy anything in our path. It’s not an anger thing. It’s a we know where we’re going thing. As a result we offend a lot of people along the way. It’s impossible for anyone to truly understand us and to comprehend our vision. Every single instance is different and it takes a serious skill and amount of bravery to want to hop on board.

    While worrying about developing a product and/or service you realize you’re depleting funds. Some are lucky to fund raise. Some have to spend their life’s savings. I’ve had to do both and I have the luxury of combining it with being married, having kids and a mortgage. There is no worse feeling than having to look into your wife’s eyes and say “I’m not getting paid for a while” when she knows how much you are worth on the open market as an employee, but you know that’s a major problem. You go so long as an entrepreneur that the only person who will want to hire you is another entrepreneur or at least that’s the only type of person you can relate to. Most traditional firms don’t see value in paying big salaries to maniacs who have trouble with NO. The only one’s who do are the type that just acquired that person’s company and rolled them into the staff for a while.

    All of this comes before you make one dollar. Think about that. It’s insane. We’re insane, but we’re wired differently and we love it. That’s the difference. We LOVE it. Personally I go weeks where I barely get anything close to consistent sleep. It’s not because I’m working, but rather just laying in bed thinking and thinking and thinking and being unable to shut off. It’s not healthy, but in my eyes I’ll make up for it after I succeed.

    Lastly, you end up being “married” to the start-up for so long that your motivation goes from “I want to do great things” to “I can’t went to break up with her and I will do anything to get there”. How’s that for attitude? I think every entrepreneur needs to hate their business in order to make it truly succeed, because it has caused so much misery, so much heartache and so much stress that you need the inspiration to go to great lengths to make it happen.

    Now who wants to be an entrepreneur?

  • SoloBizCoach

    Great visualization of the three stages.

  • SoloBizCoach

    Whoops, sorry about the last comment. I hit the button before I was finished.

    I liked your three stages. I think that a lot of people fail to make it to step three due to a lack of confidence. Some people just don’t have enough confidence to realize that they will not get knocked off the mountain. For those that do have the confidence, they will be the king of the mountain.

  • MSGiro

    Awwww crap. TYPO in the last paragraph. Damn and I thought I was typo free. NOW I won’t sleep for days over this. I need a drink. @MSGiro

  • ginidietrich

    @MSGiro Get some Old Style. You’ll be fine.

  • adventuresinexpatland

    Molli (and yes, Molli Megasko is one cool name), I happen to think you delivered on what you said you would: having worked for entrepreneurial minds, you’ve figured out how they work – in terms of what it’s like to be WORKING for them. Not what they expect or what they look for in you, what it’s like WORKING for/with THEM. Many of the comments talk about ‘what we entrepreneurs are really like’. Yeah, okay, got it. Having worked for lots of Alpha Dogs in the past (mainly in the political arena, but believe me, there are far more parallels than any of you would care to know), I think you are spot on. I’ve done all 3 of the role choices you’ve outlined, learned a boatload, had fun (and sometimes not so much), and wouldn’t regret any of it. Did I want to be a political Alpha Dog? No (and not for lack of ability), or I would have left to go do the things necessary to be one. I happened to enjoy the challenge of demonstrating to someone new (always someone new) that I knew what the hell I was talking about, understood their vision and could help them get there. The result? I was always being tapped to start up this or that for them. As I can tell you are, too, Molli. Rock on!

  • Leon

    G’Day Molli,

    Thanks for such an interesting perspective. Are you aware that most high achieving managers don’t quite figure how their staff see them?

    For some years I’ve been preaching that a CEO’s prime role in a small- medium business is marketing and PR. To achieve this, he or she must cultvate perfect employees who can handle all the day to day routine business perfectly.

    The CEO still needs to be involved in strategy. But if they’ve cultivated perfect employees, much of the strategy will be generated by the employees and pushed upwards to the CEO anyway.

    Molli, you wont find what I’m suggesting in many textbooks. That means that my idea probably has some worth.

    No CEO can successfully manage a small-medium business until they absolutely trust their staff to run the business perfectly on a day to day basis. And the less CEOs are involved in day to day issues, the greater the opportunities for employees to grow and develop professionally.

    Everybody wins.

    Make sure you have fun.



  • MichaelDurwin

    @MypctweakComputerSolutions Don’t you just hate scumbag spammers? I know you’re just sitting around in your apartment in Illinois with nothing but time to kill, but really? You only launched your site in February. Use more above-board techniques and have some patience, you’ll get traffic.

  • I’m constantly moving foward… Jumping from one mountain to the next I suppose but always with a sense of accomplishment and having learned something along the way.