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.

The Importance of Good Advisers

Being that CitySquares is my second business I understand how important it is to have advisors – good advisors – and good advisors are hard to come by.

In my first business, which I started with a technician’s mindset (See E-Myth), I brought on some “advisors” and paid the price – in more ways than one. I brought in people who I thought I could learn from, who I thought I could grow my business with and in return provide them with some real interest in the company’s growth. What I ended up with was whiteboard sessions that went nowhere too often, overly complicated product ideas, and more messes to clean up. After giving it a good solid shot for a year I had to end it. It was painful, very painful, and cost a lot of money and time. It was a good decision and I learned some extremely valuable lessons from that experience.

When Bob and I started CitySquares not a day later did we decide to build an advisory board made up of people we could a) trust and b) who didn’t immediately want something from us in return. Those two qualities ruled out a whole bunch of people over the course of a few months. We quite literally interviewed people! I remember some of them read about us in the paper when we were just starting out, and they were very eager to “work with us.” Well, what that really meant was they wanted to do any number/combination of these things:

  1. draw pretty pictures on a whiteboard and show off how smart they are
  2. convince themselves of how valuable that MBA is
  3. carve a notch into their belt – like its another credential
  4. get-in with any board members/investors for their own selfish reasons

And in return they wanted equity, a seat on our board of directors, introductions to investors, even cold hard cash.

When it was all said and done what we ended up with was a small advisory board made up of a few people who came to us in very unexpected ways, and who …

  1. totally bought into our vision
  2. totally bought into our business model
  3. totally bought into our mission for locally owned business and real world community

These advisers wanted nothing in return for their time and for their brainpower – and I’m not exaggerating. I’d press the issue with them over coffee, lunch, whatever, and I’d insist that we put something in writing – and they’d insist “what’s the rush, Ben?” and “there will be plenty of time for that, Ben.” and “let’s just get Citysquares to [milestone] first.”

These folks are my most trusted advisers today. I have the utmost respect for them in so many ways and they continue to provide immense value to me and to the company, from referring us to others/others to us, to attending various meetings, to taking calls from me at various hours and in some instances working with some of my staff on things. The value is immeasurable. And yeah, now they’re all under formal agreements with the company and I sleep better at night because of it.

The point here is …

  1. Finding good advisers is extremely hard
  2. Bad advisers can be costly – even devastating
  3. they likely end up coming to you in unexpected ways
  4. they don’t want anything in return (within reason of course – I do suggest picking up the tab on lunches, coffees, beers, whatever, and going to meet them where it’s convenient for them – always)
  5. when you got one, you’ll know it
  6. when the time is right, be sure you know it!
  7. offer them your best deal
  8. Thank them often – you’ll need them when times are good and when times aren’t good.

See you on the other side

2007 was a pivotal year for me in so many ways, mostly professionally. But as is the case for an American entrepreneur, my personal life hinges on my professional life. It’s now 7:30 on New Years Eve and Ali and I are settling nicely into our new home. Carmina Burana appropriately just came on the speakers. I’m working on a tasty Belgian beer, but it’s not quite cutting the edge. What edge? The front edge of 2008.

I’ve been a little edgy today (not unusual for me – I’ve been called “edgy” before, among other things), but unusually edgy. I feel slightly less in control than I’ve felt for the past few months. 2008 is supposed to be a big year for local search, and if Citysquares can innovate properly, can achieve some measurable success with sales, and expand aggressively (yet cautiously) we’ll be in excellent shape. But those are three big tasks for a maturing startup company. Make no mistake about it – I’m confident. I’m confident, first and foremost, in my own abilities to kick some effing ass. That’s not blind confidence (a.k.a. cockiness), that’s self-assured confidence – it’s just a matter of fact – I will get this done.

I suppose what’s got me most anxious is the changes. The foliage is changing, for the better. When the foliage changes, I get a little fucked up. It’s the unpredictability of it all, the change from comfort to the unknown that gets me a little uptight. It reminds me a lot of Michael Gerber’s E-Myth – the Technician vs the Manager vs the Entrepreneur. When I first read Michael’s book, back when I was running Atomic, I was struggling with the different ways an “entrepreneur” can run a business. The book was recommended to me and I read it front to back, listened to the audio book on the subway, and soaked it in with an open mind – then I did it again. I learned so much! It wasn’t long after that I started Citysquares – with an entrepreneurial mindset. And it happened naturally.

So here I am today, a little over 2 years since starting the company. We’ll be at 13 employees in January. We’re starting our expansion. The strategy is really being set into motion. And now, I’m like a visiting team’s starting pitcher facing some tough batters in the top of the 3rd with a tie score. It’s a pivotal time in the game and I’ve got to perform, got to give my team a chance to get up to the plate – but I’ve also got to keep plenty of fuel in the tank to finish the game.

I’m ready. I’m anxious. I’m motivated. I’m eager. I’m fuckin pissed off. See you in ’08.