Working on—rather than in—your business

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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