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Posted: May 13, 2011

Working on—rather than in—your business

It's a way to keep things interesting

Brad Feld

I spent the other day 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.

Earlier, I had a meeting with a CEO of a company I've invested 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.  I also heard from several of the entrepreneurs that they were stuck at a certain size (one at $22 million, one at $5 million) where daily activities in the business consumed all their time. As with the CEO I spoke with, 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/$2 million 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 recent discussion, 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 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, moving through their own personal evolution while the businesses growth and thrive.

In my recent discussion, 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.

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Brad has been an early stage investor and entrepreneur for more than 20 years. Prior to co-founding the Boulder-based Foundry Group, he co-founded Mobius Venture Capital and Intensity Ventures, a company that helped launch and operate software companies. Brad is a nationally recognized speaker on the topics of venture capital investing and entrepreneurship and writes widely read and well respected blogs at and He holds bachelor's and master's of science degrees from from MIT. Contact him at

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Readers Respond

Brad, I had a business coach say this to me once. It's great advice, but often hard to do. A lot seems to depend on the size of your business and the number of employees you have. The smaller you are, the harder it is to work on the business, rather than in it. Great advice, and a great challenge, especially for the small business owner. By Brad on 2011 05 17
Brad - nice short, practical story/advice. As you probably recall....Michael Gerber's books - The E-Myth, E-Myth Mastery, etc (with the "E" in E-Myth referring to the word "Entrepreneurial") - talk extensively about "working ON the business" as opposed to "working IN the business". It's been many years since I read his first book, and I don't recall any of the detail - but that was THE sticky message I remember from the E-Myth book. I think it is easy for any of us to become all consumed with the day to day activities (grind) of the business - and lose sight of and the opportunity to improve the business (the fun stuff) unless we find ways to document, systematize and delegate those day to day activities to other staff within our organizations. By Russell Straub on 2011 05 13
Brad- that's a great perspective. We tell our clients that we focus on their career while they focus in their career. Thanks for sharing this! By Ann Spoor on 2011 05 13

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