The Founder’s Quandary

After three and a half years running CitySquares, and after an additional six years running another company prior to CitySquares, I’ve learned quite a bit about starting a business and growing it. I had a bit of an epiphany a few days – I realized that I am in a quandary, caught between a rock and hard place, as a company founder, and especially as a founder running a funded company, actively on a board of directors, and working with investors. This has resulted in a new side project, a community that I am starting, along with a few others. This community is conveniently known as The Founder’s Quandary.

I’m going to spare you the details here, and let you learn about them here…

The Founder’s Quandary – the blog
The Founder’s Quandary – the Ning community
The Founder’s Quandary – on twitter

If you are a founder, please join us.

Choices and Decisions

decisions1A choice is not the same as a decision. The two are very different. A choice implies you have options, and doesn’t have a sense of conviction. A decision, on the other hand, is very much a choice with conviction. Should I have the vanilla or the chocolate? That’s a choice, but not one of conviction, I don’t suppose. Voting for Obama was a decision, a big one, and one that carried with it some strong convictions.

Today was a very difficult day for me, as founder and as CEO of CitySquares. In fact, today was one of the hardest days I’ve ever had at CitySquares because it was the culmination of some very hard decisions, decisions that affected everyone, yet that also protected everyone. These decisions challenged me in the roles of CEO and founder. Wow, how different they really are. Recently I’ve been wrestling with this for the first time. I never saw it coming.

You might suggest that the CEO says, “I look out for the bottom line” and the founder says, “I look out for the company.” The two are not the same!

As founder, I have a big vision, a huge amount of passion for this, and I’m insanely optimistic. These things can blind me. And as someone reminded me today, “that’s really your job, Ben. No one else can do it” These things are essential.

As a CEO I have to execute on the vision, harness the passion, funnel the optimism. These things, too, are essential.

Today I found myself caught in a limbo between Founder and CEO. The founder in me wants to protect everyone, make them believe that the world is a good place, that everything is going to be just fine, and shelter them from the debris and the noise and the dust being kicked up all around us. The CEO in me wants to tell it like it is and let them face these decisions on their own, and test their commitment to the company, test their will, and test the guts and passion that we asked for when we hired them.

And therein lies the point: when the going gets tough who are you? Who are you really concerned about? Who do you look out for? Do you take one for the team or do you just move forward with your own agenda.

I posted a tweet earlier this evening about today, and I was totally taken aback by the responses I got from folks. People near and far wrote me privately either through twitter or through facebook to ask if I wanted to talk about it, just to talk, founder-to-founder, or as friends. I have to say, that, in itself, meant so much to me. It reminded me how being a founder is lonely. But it’s times like these that your tested, yet again.

Choices are easy, decisions are hard. I know I made the right decisions, and doing so resulted in more choices for others. That’s a pretty powerful thing. Now you just have to hope that it all works out.