Entrepreneurial Lessons in 2009

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2009, you sucked! Good riddance to you! That was a horrible year that I just get sick thinking about. As it pertains business matters, it all started in late 2008, the second half of September to be precise, when the economy tanked. The entire country panicked, and the global economy didn’t respond any better. It really was the Global Economic Crisis, and as NPR is now reporting apparently it’s been “abated” but the effects are to linger for quite some time. One thing is certain, CitySquares was affected greatly and quite immediately. I won’t go into the details and the describe the punches we took, those we handed out, and the battle scars we have to show for it, but I will highlight some of the challenges and battles that really stand out in my mind:

  • As soon as the hard times hit I saw an immediate response by the staff at CitySquares. For the most part, the team held together and today we’re tighter and stronger for it. Like a tribe, we stuck together and hunkered down while battles and storms happened all around us. We were not well fortified but we survived and now we’re about to thrive! On the other side of the coin, a couple of our tribesmen demonstrated an inability to persevere and overcome these challenges, and some weaknesses were exposed and ultimately eliminated. Thankfully that ended rather quickly and the tribe was/is better for it.
  • Small businesses, specifically brick and mortars and mom-and-pops, got their asses kicked much like we did. Those who hadn’t yet learned to fly unfortunately fell from the nest and met their demise in ways that were hard to watch. Balances went unpaid, phones disconnected, and personal stories of financial tragedy were common. It was truly heartbreaking to see. Yet many also survived and are resurfacing with tougher skins and stronger businesses!
  • Beyond the staff at CitySquares I also experienced something completely new and foreign to me – board members and shareholders reacting in different ways. The vast majority of them demonstrated a wisdom and calmness that really impressed me and taught me a whole lot about pragmatism and experience. That, however, was not always the case. In a couple of isolated incidents I witnessed naked panic, fear, and fright and this came from the worst places possible in the corporate structure. I will not divulge the details not for lack of transparency but for reasons of respect and professionalism – that is a fine balance you know! As a result of these panicked and frightened reactions it was apparent to me that something had to change and change immediately or the company was destined to collapse for unacceptable reasons. It’s one thing to fail because a business model fails, or because of timing or market and/or economic reasons, but its another to fail because of human emotions, poor judgement, and failure to communicate and work as a team. At the end of the day, however, our shareholders demonstrated their commitments to the company but continuing to support us financially and through other supportive means. Again, we are now better for it!
  • As a leader I learned so many lessons in the past 12+ months, but two in particular that I will not ever forget. For the sake of brevity there were a few incidents in the first half of 2009 when I lost control of my emotions and let anger and fear win. These incidents are not something I care to revisit in detail and am embarrassed to detail. I have made amends in both instances. These two cases taught me some huge lessons, lessons that took me months to truly understand and apply to life and work.
  • In a tribal organization like ours, loyalty, communication, and teamwork are absolutely vital. What became incredibly apparent to me was how strong the tribe is when communication is at its best, when leadership is performing in the right ways, and when the tribesmen are truly committed to each other and to the tribe’s visions and beliefs. There is something almost dogmatic about a small company! I saw people step up to the plate in the most amazing ways. It’s still happening today. People are not willing to settle for less, nor willing to sit back and be OK with the way things are or may be heading, they expect more from themselves, from the others, and from the tribe as a whole. There is much of this happening right now, as it should always be! A sort of shuffling is happening internally, and its happening in a way that is uniting the tribe only more and making the company better and more focused and determined than ever before.

These points are the major ones that stand out for me, as an entrepreneur and as the chief of the tribe. There’s lots of business related stuff too, like how we got through the last 15 months, and what changes we made to our business/model/execution, etc. And those things are continuing to happen, but the reality is this: CitySquares is stronger, more successful, and closer to our goals than ever before! Its because of the above points, among lots of others, that we are here today.

A few of my entrepreneurial goals for 2010 are as follows, and I will soon be blogging about these things:

  1. Continue to grow and mature as an entrepreneur, as a CEO, and a tribal chief. How? Continue to identify and improve those leadership traits where I am weakest, and harness and cultivate those where I am strongest. I cannot do this alone either, I need my tribe to help me, I need to read and learn more, talk less, say more, listen more.
  2. Blog here more often, with transparency, and with purpose.
  3. Create and participate more in entrepreneurial circles, networks, and communities (e.g., The Founder’s Quandary)

I am still working on these ideas and a couple others. I will be blogging again here very shortly. Stay tuned for more!

2010 is going to be an extremely good year for CitySquares. No doubt we still have lots of lessons to learn and battles to fight, that’s par for the course. But if we can survive and unite the way we did in 2009, than 2010 is really going to be something else!

Happy new year to you all, may your 2010 be filled with new found freedom, with health, and prosperity.

Founders and Leaders

george_bushEntrepreneurs come in different flavors, different sizes, different languages, and different abilities. Some entrepreneurs are brilliant engineers, some are opportunists, some are really good at sales and marketing. One thing is for sure though – not all entrepreneurs are leaders.

There are countless books on leadership. I’ve read a few, from Jack Welch to Rudy Guiliani, to Seth Godin. In this entrepreneurial age we’re living in, leadership has taken on a new meaning. Leadership is a bit more scientific too, than say entrepreneurship. Yet leadership can also be as enigmatic as entrepreneurship.

I’ve been thinking about these things lately, thinking about the essence of leadership in an entrepreneurial setting.

Fred Wilson, on his blog, said the following the other day:

I’ve heard people say, “If you want to know about a company, all you need to do is look at the leader” and it certainly is true that companies exhibit the traits of their leaders. But it’s also true that companies exhibit the traits of their founders. In fact, I’d argue that founders leave a longer and more indelible imprint on the DNA of companies than the person who is currently running them.

There are a host of reasons for why that is. To start, the business that the company is in is more often than not determined by the founder. And companies can move into different businesses over time, but most stay fairly rooted in the initial business that they started in. It’s also true that the culture of a company is defined early on and it’s hard to change it. Some companies are technology driven, some are product driven, others are marketing driven, and others are sales driven. That most often comes from the founder and it’s hard for a new leader to change that mindset. Another important reason that the founders often have the greatest impact on the DNA of a company is the entire initial management team is most often built by the founder. That initial selection of people is a critical determinant in the way companies evolve and behave and new management will always struggle to change the behaviors a company exhibits.

Founders are entrepreneurs, whether they like it or not. That’s just inherent in founding a company. It’s like giving birth to a child, you are a mother. However, just because you’re a founder, or just because you’re an entrepreneur, doesn’t mean you’re a leader.

I recently read Tribal Leadership, by various others, and Tribes, by Seth Godin. I’m trying to better understand my own style of leadership, the qualities and the characteristics of it. I’m trying to be a better leader, and know where my weaknesses as a leader may lie in order to do so.

What I enjoy most about doing what I do every day here at CitySquares is not closing deals, analyzing Excel workbooks, or conducting board meetings. I don’t particularly enjoy any of those duties and tasks, or many of the countless other responsibilities that come with being the CEO. And none of those things actually make me a leader. What I do enjoy doing is working with the people within CitySquares, as well as the customers and the advisors. I enjoy affecting change, helping the company move forward as a single unit, as a tribe, who actually enjoy their jobs. I enjoy protecting them from the noise outside these walls, and from those who may try to stop them from succeeding. I enjoy achieving our goals, collectively. I enjoy inspiring. I enjoy seeing them smile at our holiday party, as if they’re actually happy to be there because they like the company, they like who they work for, they like who they work with. I enjoy working with my team to find new ways of accomplishing the greater mission of CitySquares. I enjoy inspiring and affecting change then watching them execute, and learn, and get even better at it.

Is this leadership? I don’t know. It’s me, I know that. It’s who I am and it’s what I do best, I think.