Lessons from an Entrepreneur Turned CEO

Gini Dietrich

This is a guest post from Gini Dietrich, CEO of Arment Dietrich, Inc.

Nearly three years ago I had to make the transition from working in the business to working on the business. It was a difficult transition (sometimes still is) because no one tells you how to do it. When I asked my peers, friends, and family what a CEO should be doing, no one could give me a straight answer.

I read a ton of books. I read every article I could find.  I brought it as an issue to my Vistage group. I asked other entrepreneurs turned CEOs. I kept a list of things I thought I should be doing as a CEO.

It turns out being the CEO of a company you founded means different things to different people. What is important to me may not be important to other business leaders, which is probably why I couldn’t find the magic answer in all of my searching.

Following are some of the lessons I’m learning in my journey to the top:

  • Cash truly is king.
  • Debt isn’t bad, unless there is a recession and you can’t get access to capital because you already have debt.
  • Big is not always better; profit is always best.
  • Leadership is not about being the first one in and the last one to leave the office, nor about working the most hours.
  • Employee communication should happen only in person; internal email sucks.
  • Just because you have three letters after your name does not mean you have to be all business all of the time, if it doesn’t fit your personality.
  • If our clients aren’t happy and want me working on their accounts, it’s because I haven’t done my staff coaching and mentoring job well enough.
  • My time is best spent on innovation, coaching and mentoring staff, landing the whales, and being the face of the company.
  • It’s okay to say no, if it’s for something not in the four areas listed above.
  • It’s good to shake things up every once in a while, in an effort to stay ahead of the trends.
  • It’s great to have friends who run competitive companies; if the relationship is set up correctly, we work very well together.
  • People like working for a company that stands for something and lives its values.
  • My gut is ALWAYS right.
  • Engagement, connection, and transparency are the most important communication tools – with employees, with clients, with prospects, with talent candidates, with vendors, with partners, and any other stakeholder.
  • Bad news does not go away and it does not get better with age; no matter how much I hate conflict, sometimes it’s worse in my head than it is in reality.
  • Having fun with my colleagues, and connecting with them as people, is what I truly love about getting up and going to work every day.

What have you learned? What do you do that is not on this list?

Gini Dietrich is the founder and chief executive officer of Arment Dietrich, Inc. and the author of Spin Sucks, the 2010 Readers Choice Blog of the Year, a Top 42 Content Marketing Blog from Junta42, a top 10 social media blog from Social Media Examiner, and an AdAge Power 150 blog. You can subscribe to Spin Sucks or connect with Gini on Twitter or on Facebook to learn more.

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  1. says

    – You have to love what you do at this level. If you don’t, the stress will kill you. Sooner or later, anyway.

    – If you’re embarrassed to promote something you’re doing, you should be doing it better or not at all. Don’t settle.

    – Care. Please, please care about the quality of your interactions with people, the service you provide, and the impact you have. If you don’t, your people won’t either.

  2. says

    Hi Gini,

    What a warm CEO-savvy post without the CEO attitude.

    I love that in listing the ways you spend your time, you list “innovation” first. I suspect that may surprise many people as a priority for a PR firm. I also like that you mention the too-little-said but far saner reality that PR firms can and do work with each other.

    The above and Spinsucks.com make you one of the people(along with Mr. DB here of course) changing the profession’s reputation from PR as “these PR people will do anything for attention” to PR as in “People Rock!”. From one competitor CEO to another: Hope you land some snow whales today! 😉

    • says

      What a nice comment, Lisa! Thank you! I see absolutely no problem in working with my competitors. It makes us all smarter and more wise…and it’s way more fun! But, having come from the big agency world, your competition was a profit center in the same building and don’t you dare think about working with them!

      I think it’s less prevalent in boutique and mid-sized agencies. So let’s find a way to work together!

  3. says

    Hi Gini

    I havn’t quite gotten to the position you have just yet – startup mode :)

    Firstly,the make item that resonates with me is the emphasis on the “people” side. I’d agree with you on that 100%. Without the people nothing happens – period. Once you have the right team on board, giving them latitude and communicating directly really does reap huge benefits. I’ve seen this in previous lifetimes!

    One thing that I am learning at the moment is that delegating responsibility is hard and changing the mindset from “I have to do everything” to “I need to run the company and trust others to get on with it” can be a challenge when you have been responsible for quite literally everything from the offset.

    Some really good lessons here – thanks a million for sharing them.

    Barney – a future CEO :)

    • says

      Well, I hope this helps. Because NO ONE talks about how hard it is to go from having your hands in everything as you build to becoming a leader (or even deciding you shouldn’t run the place and hiring a professional). The people who write about it have never done it…they’ve just coached people who have.

      I still have the delegation issue, but you get to a pain point (do I want to work 16 hours today or teach someone else how to do this) and suddenly it becomes much easier.

  4. says

    Hi Gini,
    Nice read, great attitude.
    I like the way you prioritized the things that are truly important to you and in running your business…Working smart, not hard and people.
    I enjoyed it so much that I have posted a link to your article here so that I can come back to it and read it from time to time http://www.acoollink.com/helpful-business-related-links.
    I work as a consultant and I own a startup business so I enjoy soaking up words of wisdom when I can.
    Here is an article I wrote on attitude. http://www.acoollink.com/salesman-consultant

    • says

      Hey Mike! Sometimes I forget to take my own advice (working longer hours), but it’s good to go back to it from time to time. I’m headed over to check out your blog now.

  5. says

    I’m no CEO, but I thought I’d make a couple adds to your list as someone who’s went from working for the man to working for himself in the lsat couple years:

    * Find ways to work smarter–not harder. I say this a lot, but it’s so critical to success. At all levels, really.

    * Delegate. You cover this above in a number of the tips, but finding ways to delegate to people who fill your talent gaps is absolutely key for a leader.

    * Know your weaknesses–and find really smart people to fill those gaps.

    * Don’t take competition too far. Competition is a good thing–but not at the expense of personal relationships. You never know who you’re going to work for–or with–in the years ahead.


    • says

      What? Don’t take competition too far?! Jeez. It’s a good thing we don’t work together.

      Actually, that’s been a super hard lesson for me to learn. Last year we had someone join our team who was thinking of things before me (which never happens) and I really had a hard time with it. It was a lot of self-talk before I began to really love it.

      • says

        Hola Gini

        Before I go up to the top of the comments and add how amazingly useful and honest this guest post is, I have a little story for you that ends with a question ;). I’m telling it cause it somewhat resonates/relates with what you said here to Arik.

        I’m gonna’ do my best to keep it shortER than it actually is lol.

        After I graduated college (before going to grad school) I had an interview with the CEO of a highly regarded Communications company. Not sure why my interview was with him directly but that’s besides the point. All went well, blah blah blah and the tone of the interview turned less formal. Anyhoo, towards the end he asked me where I saw myself in 10 years.

        Now since I had pretty much cornered his character and sense of humor and knew what would pass and what wouldn’t – I replied to him in a joking yet serious/sarcastic tone – “Honestly? In your chair”.

        His reply was “you’re hired.”

        When I asked him why a bit later – he said that a good CEO will always hire someone that they think can replace them. Someone that scares them in a good way – a way that keeps them on their toes and at the same time makes them look good in front of others – whether clients or so forth.

        I took it as a compliment of course – but went on to do my Masters instead.

        My question to you is:

        Do you agree with that train of thought? Would you hire someone who you know can have your potential one day to replace you? And can you usually judge that in someone right off the bat or within a short period of time? (seeing that the company is yours and in your name may be a bit different here but you know what I mean).

        Danny – your take here would also be great if you have time :).

        PS – I wanted to skip the story and get straight to the question but they say stories are nice to have sometimes hehe.

        Thanks Gin

        • says

          Now if you hadn’t included the story, it wouldn’t have been a Griddy post. I do subscribe to that theory and, funny, it’s the same answer I gave right after I graduated from college and got me hired at Fleishman Hillard. BUT. It’s really, really, really hard to find people who are both smarter than you and you respect. We interviewed a guy who I REALLY wanted to hire because he was 10,000 times smarter than me on pricing and product development. But he was so freaking arrogant that I couldn’t pull the trigger.

          The real craft is in finding the people who are smarter than you that you can stand to have around.

        • says

          I LOVE surrounding myself with people that are smarter than me.

          I know I’m pretty smart in some areas (creativity is something I think I’m good at), but I also know that I can learn so much more by having people around me that can push me.

          If you can’t take the possibility that someone is better than you, you shouldn’t be a boss – because your company is just going to stagnate under your non-growth leadership.

            • says

              Thanks a lot for taking the time to answer that guys.

              I also agree with Gini about the arrogance thing and being able to tolerate a person. I don’t handle arrogance too well.

              It’s not just about being surrounded by people that are smarter than you – cause I think like you pointed out Danny – they can be better at some things and you can be better at others – where you complement each other. I’m sure you and Troy have that.

              Totally agree with what you said.

              If you’re willing to jeopardize the growth of your company just to remain on top then you might not have the leadership traits that it takes to succeed after all.

              Bottom line: You both rock – creatively and otherwise :)!

            • says

              HAHA! Gravatar Fail. As the posts narrowed the reply button disappeared!

              Great stuff in this thread. Sadly I guess only the attractive ladies get interviewed by CEO’s. I was always sent to the assistant of the assistant recruiter for the HR company hired to screen out losers. Sigh.

              I agree with Arik and also with Griddy’s CEO. Plus he was smart because he hired her.

              And Gini I sure am happy I met you after your evolution. Would of been such a long journey reprogramming you to be more Taoist. Very impressed you started on your own.

    • says

      Haha, thanks Gini – but hey, well worth the wait. :)

      As someone in the same boat (along with Troy), I definitely recognize a lot of the points you make here. It’s not an easy transition, and though we don’t have full-time employees yet, we have some very special relationships with “unofficial” parts of Bonsai.

      Which leads me nicely to something I’d add – sell your strengths and buy your weaknesses.

      We’re not that almighty fonts of expertise or skills, so don’t try and fudge that you are. If you can’t do a service yourself, outsource to a trusted provider.

      Just because you can’t doesn’t mean you don’t.

  6. says

    Aunti Gini- I feel a bit bad calling you that because you look much younger than me in this photo.

    I am no CEO but when I read your lessons (yes not learnings :), I think many are very relevant to us smaller entrepreneurs.

    Thanks for showing us that being a CEO is no walk in the park and that CEO’s are people to.

  7. says


    As an owner of a less than year old company your list rings true. I’ve led hundreds before and been responsible for millions of dollars worth of money and equipment but starting from the ground up is different. It feels like I have little room for error.

    But we’re moving along slowly but surely.


    • says

      Oh you have lots of room for error. It’s just a different kind of error. You learn things you didn’t know before…such as what it’s like to lay in bed at night and wonder how you’re going to make payroll at the end of the month.

  8. says

    Engagement/connection/transparency – I *love* that!

    When I’m in this space, I really find those deeper connections. And in the end of the day, that’s really what it’s all about for me – the connections I have with others. (well, that…and when I really *feel* that I’ve made a difference) (…and found a place for fun and laughter in my day…)

    Great stuff!

  9. says

    Hello There Gini!

    What a breath of fresh air! PLUS…you’re a whole lot better looking than Danny!

    You very elegantly cover things that I had to learn at the ripe old age of 25 (33 years ago). I had started a home health care company at a very opportune time (through no conscious planning on my part) and almost instantly had 85 employees, 6 locations and the beginnings of an ulcer.

    What you say…if you can make yourself actually do them on a routine and unthinking basis…will serve both you AND your company well.

    My best to you, thanks for sharing your thoughts, I appreciate them.

    Dennis Lively

  10. says

    Thanks Gini for sharing this.

    For sure can relate to “Bad news does not go away and it does not get better with age; no matter how much I hate conflict, sometimes it’s worse in my head than it is in reality”…

    Last year I made a comment here on Danny’s blog about a little wicked mole I have out in my yard. I learned that if you keep follow someone that don’t really see where they are going, you kind of end up going in the same direction. And you just end up making the problem bigger. Though some suggested a snake would solve my problem I followed my gut and realized my dog could do the job. I might had found the solution earlier if I had the dog whisperer here.

    Now I need start learn how to fish for whales.

    I digged the info on Spin Sucks – cool to see some Hotel articles there also.

    Cheers.. Are

  11. says

    What an awesome, awesome post. The first 3 things in the list are probably the most important. Well, I guess the same could be said for all of it, but I know for me personally as a multiple small business owner, it took me a little longer to realize a few of those things. Abusing cash when young in business is easy, I now clearly know that Cash is King.

  12. Mick says

    Thank you Gini, inspirational and extremely useful pointers indeed.
    I’m about to go after a GM role with a company which I have actually been a customer of for a few years. This position will involve me guiding a team slightly larger than I’m used to, which if I’m honest is going to be my biggest challenge. You have however put this and some other key factors in context very succinctly for me with some excellent fundamentals to focus on. I find myself reading everything to do with management and this has very much resonated with me, so thank you.

  13. BrentHay says

    I will be referring back to this list again and again until I no longer need to. I’m a freshly minted CEO and appreciate such a well-thought-out barometer that examines the role from so many different perspectives.

  14. says

    All I can say besides this being a great and honest post, is you have it lucky young lady. CEO is nothing. Try being Chief Alien someday. Not as easy or glamorous as it sounds. But one day, if you work hard enough, you may earn your Star Fleet Commanders Badge if I sponsor you with the Emperor.

  15. Johnny Russo says

    Gini, that is great advice. I am working full-time for a high-tech company, and also working on a couple of start-ups. Your leadership tips are greatly appreciated.

    Also, to the comments about hiring smarter people, that has been Google’s mantra. The Google Way speaks to that. Google managers hire people smarter than them. And yes, while you must gauge their arrogance, there is nothing wrong with confidence to do a job well.

    One question I do have (to both Danny and Gini and anyone else that could answer): How do you know how large (in terms of employees) your company should be? How do you know when to hand off tasks that are getting too cumbersome for you to do daily? I find myself in that position often. Doing it myself, but doing too much. I know to be a leader, it’s important to train, mentor, and hand off tasks to your employees. When do you do that?

    • says

      Hey there Johnny,

      Great question, and one that I’m sure most people (employers and employees/managers) find themselves asking at some stage or another.

      The way I always look at it is when it looks like it’s going to impact on the core strengths I bring to the business.

      My role is to get creative with strategy, and think of ways that campaigns can completely step outside the box (as well as run “normally”) to stand apart from what everyone else is doing.

      If I’m having to look at lead generation, new business development and accounts (something that others in our business do way better than me), then I need to look at whether we need to outsource to more people. Worked so far! :)

      Hope that helps!

    • says

      I haven’t read Danny’s response yet, but this is how we track: 1) Am I getting involved in the day-to-day again (if the answer is yes, we need to hire), 2) Is every member of our team at capacity (if the answer is yes, we need to hire), and 3) Have we grown both revenue and profits from last year (if the answer is yes, we need to hire). We look at all of these things once a month.

      There is a transition that you go through when it takes much more time to train someone than to just do it yourself. That’s when you know you MUST teach someone else. My mantra is this: Someone should be able to do your job should you win the lottery and not come back to work. That includes me.

      • says

        Gini (and Danny),
        Great advice on when to hire and thanks for sharing your hiring threshold levels. I’ve been faced with that lately and know that when I’m spending time on the phone with non-revenue sources (i.e., AT&T), it’s time to hire that assistant. I also found, much to Griddy’s point above re: hiring someone smarter than I am and who’s able to push me and my limits, I’ve also found that timing is everything with that one. While I was tempted to do that with this latest new hire, I didn’t. Not only was the personality not quite right (arrogance does not equate to ‘so smart I just can’t live without you’), the timing for my company wasn’t right either. I’m in growth mode, but I just can’t be in hyper growth mode at the moment. I have to look at my total package (family, business, environment) and grow at the right pace for me. So, today’s new hire is my AWESOME assistant. Tomorrow’s new hire is my Client Manager.

        Thanks, as always for your genuine experiences and your sage advice shared so willingly with us all!

  16. says


    This post is one I’ll be sending to my small business clients. Making the shift to CEO can be challenging. One of the biggest difficulties small business owners face when shifting from being the technical expert to being the CEO of their business is trusting themselves.

    Trusting yourself lays the groundwork for hard decisions, noticing when you sabotage yourself, delegating things that aren’t the best use of your current skills (or interests) and acting as a genuinely positive model and mentor to everyone in the company. Actually the list could go on and on.

    I wish you every success and I look forward to hearing how Arment Dietrich does with you at the helm. My guess is you’re going to do all right!

    • says

      Thanks Elli…both for the compliment and sending this to your small business clients! It’s not easy, and some days I have to turn off the voices in my head, but it does work.

  17. says

    Hi Gini
    I’m never likely to be CEO but I have worked for some good guys.

    The stand out quality was that I wanted to do a good job for them.
    They were all obviously in charge but I admired them, I respected them, guess I felt safe with them at the helm.

    Difficult to put rules to good CEOing, but we all know a good CEO when we work for them.

  18. says

    Hi Gini — you’ve covered the following three things in your list — but I’m just going to say them differently.

    Without Vision – people perish, and so will your company. You need to have the big picture – the who, what, where and why — and how they relate to your immediate and long term future.

    Effective Leadership – people, personalities and leading the motley crew… sometimes little things like ego’s, politics and foolishness can bog down big aspirations and progress — you need to effectively manage those people/personalities [the crew] and keep them focused on the bigger things at hand.

    Responsiblity – leading anything requires your willingness to be responsible for everything. It’s lonely at the top.

    There I said it and didn’t even use profanity (haha)

    Man — your face is plastered all over the internet – people must think your pretty cute :)

    • says

      It’s Global Domination…one blog at a time. Not even blog post…entire blogs. Notice I’ve been on here twice this week?! And over at Troy’s, too?! I’m taking over Bonsai!

      Vision is SO RIGHT! It took me a long time to figure out where we were going and how to communicate it. Now I say three things over and over again…don’t forget our community, don’t get complacent, and keep fighting the fight so we have F you money. It keeps everyone motivated.

      And I said it WITH profanity.

  19. says

    Gini –

    Great, great tips! I really resonated with the it’s ok to say no if it’s not one of your main responsibilities as a CEO.

    I have a hard time saying no to people – whether they be friends or clients. If I could do it and it was asked of me, I’d try my best to do it. Worked out horribly! I hated the tasks and didn’t have time to do the things that really mattered. So, I stopped taking requests if they weren’t what I do best or be interested in learning/expanding my services in. Much happier and productive for it!

    And yes, even as an entrepreneur, I know cash is king. Cash talks in a way credit just doesn’t. Makes people stand up and listen.

  20. says


    Having also run a manufacturing business, I would add only one more Incontrovertible Law: Nothing is More Important Than Your Customer. Everything begins with what your customer needs, or perceives they need.

    Satisfy those needs and you’ll potentially have a successful company. Fail to meet those needs (which, by the way, may never actually be mentioned) and you’re guaranteed to fail.

    And its corollary: Nothing Takes the Place of Meeting Your Customers Personally. You can’t truly understand what your customers’ needs are if you don’t meet them face to face and listen to their stories. Do it regularly and you’ll have nothing but raving fans and enough ideas to fuel your innovation machine for years.

    But I have the feeling you already know these rule intimately.

  21. says

    Working ON your business, not IN your business to me is the hardest part. These are my two faves:

    •If our clients aren’t happy and want me working on their accounts, it’s because I haven’t done my staff coaching and mentoring job well enough.

    •My time is best spent on innovation, coaching and mentoring staff, landing the whales, and being the face of the company.

    Thanks, as always, for sharing.

  22. says

    Hi Gini,
    I am not a CEO and i do not have any experience with CEO`S. I am just a kid about to graduate from college in a few months. I read the post and it was really great reading it. The points are real good.
    Adding to your points, I think it is always important how you treat your employees, the way treat creates a sort of respect on your part. If you are like yelling at them and what ever, they feel like this ” its my fate that i am working under her”. If you give them a bit of boost like ” good work done”, they will try to better. I can say that a compliment is better than a million bucks for your employee. I just felt really happy reading the comments. I really think customers have to be dealt in face to face.Leadership is based on how much you well you can lead a team, not on how well you can control them. I am too young to talk abouts debts and stuff. I feel that the worst employee you can rather image can be turned into a shining diamond by just polishing. Here, the polishing is the encouragement and stuff you give him to do better. It is sometimes good to scold in case of mistakes and assume that the guy will correct it next time. I can not speak anymore. It was a great post altogether. Thanks .