Entrepreneurial Lessons Learned

Two of the most important and valuable lessons that I’ve learned over my past 10 years of entrepreneurial experience is the following: work on the business, not in the business, and do the right thing with your business. These simple concepts are actually quite difficult to consistently execute on and as far as I can see, they’re the difference between building a typical business and a great company.

At my previous company I frequently found myself dealing with A/P and A/R, collections, or dealing with technical challenges, project management, sub/contractor matters, and more. At the time I would have told you that I didn’t have a choice because “someone’s gotta do it and if it’s gonna get done right, it better be me.” Something else I found myself doing quite a bit of, which I greatly enjoyed, was working closely with customers. And it’s interesting how this concept of “working on the business, not in the business” can be somewhat confusing. To some, working with customers might be considered working in the business, and it can be, if the context is perhaps more operational and tactical than strategic. At CitySquares I frequently interact with customers. In fact, I have my own accounts that only I handle. These are my projects, if you will. I experiment with them and use them as case studies to learn more about their needs and keep my finger on the pulse of the local market. I also interact closely with community organizations like Somerville Local First, among others. This kind of finger-on-the-pulse approach is very much about working on the business.

Along my way over the last few years I discovered two books that made the biggest difference in my professional life. The first is called the “The E-Myth Revisited: Why Most Small Businesses Don’t Work and What to Do About It” by Michael Gerber. It’s written well but with over-the-top case-and-point scenarios, but it definitely hammers the point home. This book was a sort of kick in the ass for me and it helped me, as Mr. Gerber might say, “stop baking pies and start building a pie company.” It’s essentially about the mindset of the founder (technician vs. manager vs. entrepreneur). And it was the E-Myth that helped me start CitySquares with the correct mindset, and I’m constantly reminding myself of this and working to improve upon it. The second book is called “Small Giants – Companies That Choose to Be Great Instead of Big“ by Bo Burlingham. This book helped me see a bigger picture, one about being more than a business, one about being a responsible company, a company that gives a shit, that does the right thing by it’s customers, by it’s employees, by it’s community. It’s also about socially responsible business and that’s something that’s baked into the DNA at CitySquares. I highly recommend both of these books to any entrepreneur out there.

I guess my point here is that while some may tell you to “work more on the business and work less in the business” it’s a lot harder than it sounds. One can’t just wake up one day, 5 years into the business, and make her business grow, or change its culture, or its mission. It’s just doesn’t work like that. What she has is baked into the company’s DNA from day 1 and, in my opinion, it’s very difficult to change (although it can be done). If you’re an entrepreneur, or on your way to becoming one, make sure you understand these concepts, make sure you really get it and if you have any doubts about this be sure to pick up the E-Myth and Small Giants.

Finally be sure to buy these books at an independent bookstore! If you’re in the Boston area you can find a locally owned and independent bookstore at CitySquares.com. Really, get off your butt and visit one. Trust me, Amazon will survive.