The week after we sold Community Connect Inc., I didn’t receive any calls from Executive Search firms. I remember waking up early one morning and feeling panicked not knowing what I was going to do next and more importantly that no one really cared. Well, that didn’t last long as I soon started getting calls and being pitched CEO gigs. When we sold Community Connect, we had about 130 employees and we were generating about $20 million in revenues. Was the next stage of my career growing a company to over 1,000 people and 9 figures in revenues? I had to take a step back and decide on what I really valued and liked to do. Selling Community Connect gave me this enormous gift of having some financial independence and allowed me to focus on what was going to really make me most happy. So I reflected on the 12 years of running Community Connect and tried to recall the periods in which I was happiest and soon realized that I had the most fun in the early days. Yes, I was in my early 20s and we were pioneering the concept of social networking before the term “social networking’ was even coined but what really made it so enjoyable was the people. The environment and energy was incredible when the company was less than 50 people. We all felt we were really “in it” together, everyone had this great entrepreneurial energy and most importantly we all became friends. There was no sense of “corporate culture”, no formal corporate communication plans, no corporate processes. Just a group of people trying to make things happen. Organized chaos among a group of people that really enjoyed working and hanging out with each other. That is what I missed.
I described this to a good friend and mentor – Bill Lohse. Bill has had a very accomplished career including being President of Ziff Davis Publishing and he told me that what I longed for again is when a company is a family or a tribe versus an organization. When a company is less than 20 people it really is like a “Family”. Everyone is incredibly close. It doesn’t mean that you all get along at all times but there is a level of connection and loyalty that is so powerful. Everyone knows what is going on, there are no secrets. Not because there are formal communication plans, it is because that you are all working so closely together that this complete openness is just organic. When a company is between 20 and 50 people, it is like a “Tribe”. The connection is still really powerful and there is this great underlying feeling of support from one another. Greater than 50 people and especially over 100 people is when the company becomes an “Organization”. There are HR policies, formality, hierarchy, roles and structure. I enjoyed the challenge of growing an organization but I longed for the days of the family and tribe. To this day, I think about those family and tribe members. My family, there were obviously the co-founders: Pete, Mike, Cal and Grace. Then there were those people that joined and help grow our family and tribe,: Betty, Omar, Candace, Ian, Stephanie, Alexis, Bea, Rashmi, Gary, Dan, Zakia, Edmund, Maheen, Mallie, George, Arul and Kingsley to name a few. Those were amazing times and we all keep in touch one way or another. Watching our careers evolve, attending each others weddings, celebrating the birth of our children. I feel that the impression that was made on us from those days will last forever and be something that we all cherish. I know I do at least. This may be the biggest reason why I wanted to get back into start ups. Having a chance to work with a group of people as a family and tribe is truly an awesome experience. It may not be for everyone but I know it’s for me.
Ah-ha 2.0 
Ben,
You describe the norm and you are too exceptional for that. Whether a company of any size “feels” like an organization, tribe or family clearly depends upon the “culture” (almost a dirty word in your piece). Your families, professional and personal, are hostages to their cultural DNA. However, great executives, like you, can overcome a limiting DNA and transform an organization into a tribe or family, or vice versa. Company and people needs, plus love of work and colleagues, help to define the appropriate culture.
bob
Great point Bob I always appreciate your insights.
[green card]
Great leaders foster great families. Size does not matter. People do.
Ben,
I love this posting and have talked about it several times since you first mentioned this concept to me. I’ll be passing this along to all the people at SinglePlatform as well as the “family/tribe” from SeamlessWeb as well.
Thanks again for meeting up for lunch.
Best,
Wiley
Thanks Wiley. Greatly appreciated. Your feedback from the panel was what inspired me to write the post. I think it resonates with all serial entrepreneurs. You obviously have had that experience at Seamlessweb with the amazing people there and I am sure will have it again at SinglePlatform. Thank you for sharing!
Great post.
I do think that size and stage of company matters. There is a certain point (this is different for every company) where things do change, despite the goals of the leaders and the great people they hire. In my experience, that 100 person number is when things really start to shift from “start-up” to “organization.”
Beth – I agree with you. You hear these amazing stories about companies like Zappos where they can take a larger company and build an amazing culture and still keep it like a family like feel. However, it takes so much work to make that happen. In Zappos’ case, they moved the entire company from SF to Las Vegas forcing all those that moved to have to be close friends b/c they didn’t know anyone in Las Vegas. They also built so many practices and communication mechanisms to maintain that feel. What they have done is incredibly admirable. However, I still think that type of culture is very different from the organic one that you have in a small start up. I think there is a much greater feel of authenticity and sense that you were not “sold” on a culture but was really part of building one.
I found your comment about Zappos rather interesting in light of the recent CNN article – http://tech.fortune.cnn.com/2012/01/23/tony-hsieh-las-vegas-zappos/ . It seems like Tony Hsieh is trying to build an entire mini-city with some of that culture.