Working On, Rather Than In, Your Business

I spent the day yesterday in Kansas City at the Kauffman Foundation with about 20 women entrepreneurs who were the E&Y Winning Women from 2008, 2009, and 2010. As part of their program, Paul Kedrosky and I spent the morning talking to them about accelerating their growth, dynamics around financings, and boards – mostly about how to build a board and use it effectively. It was a great day – awesome energy with stimulating discussions. In addition to a great discussion, I learned a lot in my continuous quest to better understand dynamics around gender in entrepreneurship. I also met some amazing women.

On Monday, I had a meeting with a CEO of a company I’m an investor in who was frustrated with his role in the business. He had grown bored and restless with a lot of the work he was responsible for and felt like much of what he was doing was a grind that wasn’t inspiring to him. At the event yesterday, I heard from several of the entrepreneurs that they were stuck at a certain size (one at $22m, one at $5m) where day to day activities in the business consumed all of their time. As with the CEO I spoke with on Monday, I heard frustration about the daily grind and a lack of enjoyment and stimulation from the business.

I remember this feeling very clearly from my days running my first business. At about 20 people / $2m in revenue I got very bored. I was very busy, so it wasn’t lack of things to do, I just found the things I was doing to be excruciating dull since I’d been doing them for a while (at least five years). At the time, I struggled with how to address this; we ultimately ended up being acquired before I really felt like I figured it out.

During our discussion yesterday, one of the entrepreneurs brought up the notion of “Working on your business, instead of just in your business.” I heard this line many years ago but had forgotten it. It hit me right between the eyes as something that captured the conversation that I’d had with the entrepreneur on Monday and was exactly the correct notion to summarize the way to address the boredom of the endless business grind.

My friend Matt Blumberg at Return Path has really mastered this. He writes about it a lot on his blog Only Once (in fact, his blog is a tool for him to explore the issues that a first time CEO faces, since you are only a first time CEO once.) But it’s reflected in the impressive business that he and his team have created. Tim Miller at Rally Software is another entrepreneur that I have immense respect for and when I think about how he spends his time, much of it is working on the business. These guys have both scaled from CEO of a raw startup with a few people to CEO’s of 250+ employee companies, while moving through their own personal evolution while the businesses growth and thrive.

In the discussion yesterday, I kept thinking that a CEO’s need to spend more time working “on the company”, not “in the company.” Of course, there are loads of tasks in the company a CEO has to do. But having the balance shift all the way to never spending any time on the company is a huge mistake. Plus, it leads to the inevitable grind that I once found so unsatisfying.

To all the women I spent the day with yesterday – thanks for exposing me to your stories and spending your time with me so I could think through this more.

  • wow did I need that post. fortuitous timing. thanks.

  • Anonymous

    Great post Brad. I just spent 50% of the past week working on refining the vision and goals of Balihoo and came away energized and mentally engaged in the business. One other thing I believe is really important is to engage your senior executive team in the same way. One way is to have a structured process by which you force your senor team to step back and work ON the business as well. We use quarterly off-sites to force really strategic engagement at least once every three months. But we also have weekly and monthly exercises to ensure the entire exec team is stepping back regularly to work ON the business – its amazing how much it helps.

  • For any of your blog readers who want more about ‘working on rather than working in’ your business check out Michael Gerber’s e-Myth. It is the first time that type of phrase has been mentioned in that manner – though the idea has been around for a long time. That line of thinking has helped shape tons of entrepreneurs over the year’s.

    • Yup – e-Myth is a great book and I think you are right that it’s the origin
      point of the concept.

  • As one of those Ernst & Young Winning Women, I can’t thank you enough for engaging in a “real” conversation. One of the best parts of E&Y’s program is that I’m now fairly used to being in a room full of badass women. But what makes this program so amazing is E&Y’s commitment and ABILITY to get stand-out men like you, Paul and Scott Case actually participating in the discussions.

    I appreciate the courage it takes to not only admit flaws, weaknesses and insecurities that often hold us back as individuals. And more importantly I appreciate your willingness to go deeper and explore the underlying emotions that actually make me reconsider my gender thinking. I’m coming to believe that male entrepreneurs aren’t THAT different from women. After 41 years, I’d nearly given up trying to figure out how men think b/c for most of those years I’d heard, “What you see is what you get.” And finally b/c of rare days I’m privileged to spend w/men like Brad, Paul & Scott, I’m getting to ‘see’ underneath the hood. Despite being married nearly 20 years (to the same man), I truly didn’t believe most men were as flawed as my husband. (See – it sounds harsh to get real). But it’s a reflection of my thinking not my husband. Me saying it aloud doesn’t make it true. Actually…saying it out loud and talking through it is what made me realize it’s not true!

    I think it’s often overlooked or undervalued (perhaps b/c in hindsight honesty seems so obvious AND uncomfortable), but the coolest part of being at Kauffman Labs (other than the kick-ass facilities and amazing Kauffman team) was seeing the shift in the room so that those badass women felt a lot less like posers pretending to be secure, badass women.

    My experience is I’m often playing two games at once (one real and one imagined). AND that’s what I realized MUST STOP! I can speak for myself but my hunch is that many women’s honest experience if they’re willing to dig deep is an empowering (and sad) truth: I really am the biggest thing holding me back. It’s not men. It’s me! (And yes that’s a generality b/c there are absolutely real cases where it IS MEN).

    My take-away from the event is a commitment to focus exclusively on the real-life group sport of entrepreneurship and to STOP the distracting head-game I play all by myself that’s clearly a make-believe game of dress up where I pretend I’m as confident as all of the men in the room clearly believe they are. I’m not saying men and women are the same. Women and women aren’t even the same. I’m simply saying I’ve decided neither is better. We’re all flawed. We’re all insecure. AND we’re all good at our own thing in our own way.

    My commitment is to get out of my own way. Fortunately, iTunes makes it BIG fun to shout my new mantra at the top of my lungs, “I’m on the right track baby, I was born this way!” And a special shout out to Lady GaGa b/c thanks to her I finally have my very own Theme Song. Talk about badass!

    • Susan – awesome, heartfelt, and deeply thoughtful comments. One of the powerful things about yesterday for me was hearing the way the group of badass women talked about things. Y’all were an amazing group and while I often get doses of it from the female entrepreneurs I work with, the concentration of focus and energy was super powerful. I’m glad it was as powerful / useful for you!

  • This has been the main 2011 goal for my co-founder and myself. A great summary of this is from Derek Sievers, Founder of CD Baby – Delegate or Die –

  • You can’t let yourself become an employee of your business. You have to duplicate the efforts you put in to founding your company throughout the life of your company to continue to grow. A lot of the time this has to be a time blocked exercise every week.

  • Scott

    Susan – glad to see you are taking action! Keep challenging your assumptions in business and in life!

  • Scott

    Susan – glad to see you are taking action! Keep challenging your assumptions in business and in life!

  • Rich

    Common problem for the go-getter, do-it-myself, entrepreneur type person.

    Isn’t this the reason many boards want to hire a “professional leader” instead of letting the founder or entrepreneur run the company? Founders/Entrepreneurs make the business their “baby”. Which is great at first, but eventually works against growth and success.

    • Sort of, but I think the better boards (and investors) work to help the entrepreneur learn how to scale up to be able to manage the business, if he/she wants to. In my world, the best founders are the ones that want to run their companies forever.

  • David Mandell

    Based on my experience, most CEO’s that feel that way have a lack of ability to trust others on the team. Until they can free up their brain space by trusting others to get stuff done, they can’t get out of their day to day and focus on the business instead of in it.

  • This is very common when tradespeople move to entrepreneurship. I.E. a baker opens up their own bakery. I think it’s essentially the entire premise of The E-Myth book.

    I think in general tech entrepreneurs in the high-growth areas experience this less because they often found with a business-focused partner and have a vision for that growth, as opposed to just coding because they are good at it and wanting to do it for themselves.


  • Susan, great take on the meeting yesterday. As one of those EY women who read E-Myth, I think you can take the concept of working on your biz a step further. While you don’t have to be an actual parent, think of yourself as the parent, not of your company, but of the idea/asset you created, the essence of your company. A child will be stymied in life if the parent smothers its child, is overprotective, etc. At some point you need to let the asset of your company go. Perhaps some of us entrepreneurs are afriad of becoming empty nesters, saying good-bye to the asset. For many entrepreneurs, conceiving new ideas can be orgasmic. So, go have fun and create new ideas/assets. As parents of our ideas we need to evauluate if we are making the asset go bad. There are all types of parents and they come in both genders. So, Susan good for you to say that “We’re all flawed. We’re all insecure. AND we’re all good at our own thing in our own way.” Thank you Doug. Paul and Scott Case for being so candid with us all. Most importantly thank you for sharing that life advisors are just as important as a board of advisors. Refreshing to hear from such accomplished individuals that what affects you personally impacts your company and to seek out life advisors that can empathize and share how they got passed similar struggles.

  • This is also the idea in the E-Myth. Think of your business as a machine that you’re building and perfecting. Nice post, Brad.

  • Blevine

    I was fortunate to be one of those Ernst and Young Entreprenuerial Winning Women at the meeting in Kansas City. Brad, thank you for sharing your time and knowledge with all of us. We were inspired, and speaking for myself, energized by your insights. Scheduling time to work on, rather than in my business is one of the “action items” I took away from the Kaufman Foundation experience. I look forward to following your blogs and thoughts in the future.

  • Jill

    Brad, thanks for the important distinction as well as your suggestions in Kansas City for how to develop a discipline around doing this. Prior to our discussion, I hadn’t realized the significance of boredom and how it can be: 1) symptomatic of a failure to delegate, 2) a dangerous temptation to diversify into other products/markets and/or 3) a situation that can tear teams apart if it becomes the white elephant in the room. To Susan’s point, prior to our meeting, I’d probably have chalked boredom up to a sign of my inadequacy as a leader, rather than an important touchstone that can help me to stay on track. Thanks again. Now, I’m off to design a new pattern inspired by the amazing “Mexican voodoo meets Parisian paisley” shirt you rocked in Kansas City. Stay tuned!

  • Anonymous

     Working on your business also means doing everything you can as to transform it into a source of continues capital. This may also sometimes mean the need of raising initial funds which can help you expand. If you want to understand how to professionally approach that job, just read the article here: