It has been a while since I posted to this blog. I have spent the last 3 months out in Asia. I did a little work but it was definitely mostly pleasure. Great to get away from things and have time to think, reflect and clear the mind. So I have been back in New York for about 2 weeks and recently had lunch with a friend who is a CEO of a publicly traded Internet company. He asked me during that lunch that now having sold and no longer being a part of Community Connect if I had reflected on what I would have done differently. It is a funny question because I have thought about it but mostly by recounting specific incidences or situations and not pulling it all together to give an overall assessment. I ended giving an answer but I think it was a lot of rambling and if I could take a mulligan, this is what I would ultimately say would be the 1 biggest thing I would have changed:
I was Too Deep in the Weeds and not Strategic Enough.
To say the very least, I was a very hands on CEO. I know this was a flaw of mine. I often deep dived into certain business operations and initiatives. For a company of about 100 people, I think it is inevitable that you do that once in a while to make sure that the “factory” is running efficiently but I was in it too much. Trends and dynamics in this industry change so quickly and you need to be on top of it. I should have been better aware of our competitors, technology trends, VC dynamics, potential suitor situations and shifts in the consumer market. I didn’t have my head in the sand but I didn’t spend nearly enough time understanding how the dynamics that affect our business was changing. Someone once told me that “Timing is Everything” and I realize that it’s not about being lucky. Instead it is about grasping market dynamics and being able to “time” the best way to react to those changes especially when they hit that watershed moment. For Community Connect, I saw the wave of Social Networking 2.0 sites (Friendster, MySpace, Facebook) but didn’t fully grasp how much of a tsunami it was going to be. The change that happened in the industry was incredible from consumer behavior, advertising demand, traditional media needs and venture capital funding. Our path is that we should have either made a bigger move earlier or we should have been bought when we were in more of a leadership position. We took too much of a middle of the road path and that was not the way to react to such a huge shift. Some people say to me “how can anyone have anticipated that type of transformation?”. I should have been able to anticipate it. We were leaders in the market with the most experience in building a successful online community business. I should have completely predicted how quickly social media was going to take off. Timing is everything. These monumental shifts happen. You just need to be prepared to take advantage of it. I won’t make that same mistake…..trust me. 🙂
Ah-ha 2.0 
Having worked in many start-up contexts, my experience is that finding the balance between strategic focus and operational focus in no small task. Many of the CEOs I know – at both large and small companies – describe this balancing act as the one thing that is necessary to get right. Over focus on strategy; nothing gets done. Over focus on operations; lost opportunity, products that do not delight, etc. Is there a perfect personality type or organizational configuration to address this challenge? Probably not. When I was at Reunion.com, the CEO and I split operational focus (He focused on acquisition marketing operations and I focused on product marketing, management, and development) and we shared strategic focus. At other companies I have seen these focus areas split across a CEO and COO (classic approach). And sometimes, rare at scale, a CEO can handle both.
Anyway, my simple comment is that the challenge you describe is THE challenge of running a company and DEFINITELY a startup
David – you are right. This is definitely a huge challenge in running a start up. We actually had a COO and a very good one when the “wave” happened. We split operational duties and also shared strategy. We still “missed” it. I think it is not just having the time but also being in the right mindset to anticipate big industry shifts. You almost have to be seeking it out. It is so hard to do. That is why you need to hire former CEOs as Strategic Advisors to be seeking those changes out. 🙂
Hindsight is always 20/20. Few ever score on the first try. You may have heard Tom Monaghan of Domino’s failed several times before he realized he was selling a delivery service, and not pizza (hence why theirs taste like cardboard).
Typically the answer is to hire the best employees/partners, but you apparently you had an excellent COO. So there must have been something about him to make you reluctant to relinquish control to him, or your organization suffered from group think (where no one dared to challenge the status quo), or you were simply too busy.
Still, you should be proud of the organization you built, and take the lessons you learned and move on to your next venture.