We’ve all sat at our family Thanksgiving table and said to ourselves “I wonder if every family is this dysfunctional?” If it’s any consolation, there are dysfunctional families that come with every entrepreneurial venture. Our early teams will almost always be dysfunctional. The criteria for early team members is not what needs the business has, but who is crazy enough to leave their job, or has enough free time to spend on your idea. It is like the movie “The Replacements” in which NFL players go on strike and a motley group of new players, led by Keanu Reeves as their quarterback, are brought in as replacements. There is a convict, two drug dealers, bouncers from a night club, a Fijian wrestler, a chain-smoking placekicker, a deaf wide receiver, and a psychotic police officer. Welcome to your dysfunctional family.

If someone gave us enough money, we would recruit based on need, and at a level of experience commensurate with the size of our vision. Unfortunately, that almost never happens in the early stages of businesses. Our initial team members are often those whose level of experience is below what is needed. They may work their asses off, but there will be gaps.

We are going to have gaps in our team. We may also have team members that are not used to the pace or the pressure. These may be ongoing skill gaps or just a lot of blips along the way. We had plenty:

  • Did your CTO quit again? I will be forever indebted to my first CTO. We are still friends to this day. He runs his own business now and one of the nicest things he ever said to me was “now that I run my own business, I find myself thinking some of the things you used to say when I told you that you were crazy.” Back then, however, it was different. He used to quit once per week. To say the market was new would be an understatement. When we started selling our incentives model, we tried to include the most important features for a platform serving this market, but we were not sure. My CTO had come from a traditional software development world with a waterfall development process and software releases. You didn’t “kind of” release software. You scoped it, built it, tested it and released it. Once you did, right or wrong, it did what it did. I would regularly come back from meetings with Fortune 500 companies with a high level of interest in our solution but each had requests for different features and functionalities. When I communicated this to my CTO, he would give me analogies like “when Crest launches a new toothpaste, do you think you get to go back to the store and say “can I get more fluoride?” When Microsoft releases an operating system, do you think you get to call them and say “can you move the Edit menu to the left?” We had this debate over and over. Of course we wanted to get to the point that the market was defined (hopefully by us) and our software releases were strong enough to not require major change. But the market was very new, and we needed to be flexible and willing to adjust to market feedback. These debates were no different than any other early stage company delivering a new product into the marketplace. Unfortunately, these debates not only became fruitless but they lead to him quitting once a week. I would talk him off the ledge, and then we would do it again the next week. I used to date a girl on and off at that time and when he called in the middle of a date, she said, “did your head of IT quit again?”
  • This is experienced? We had prepared for this meeting with Blue Cross Blue Shield of Florida for several weeks. We were finalists for their RFP to be their reward vendor. I traveled to Jacksonville, Florida with one of our sales people who had spent fifteen years selling to health plans like Blue Cross Blue Shield of Florida. One of the things we wanted to know for every meeting like this was the major employers that a health insurer like Blue Cross Blue Shield of Florida insured. This was standard operating procedure for any meeting with a large health plan and would be so for any experienced health plan salesperson. We met in their lobby for him to brief me on details. I asked him who their major employers were and he looked at me like I had three heads. I got angry that this simple request had not been fulfilled by an experienced salesman. As my blood started to boil, I think the entrepreneurial gods were mocking me because when I looked over his shoulder in their headquarters lobby there was a big wall with the logos of all the major companies that they insured. I told him not to ever show up for a meeting without doing his homework, and then to, “turn around.”
  • Knock-off? We hired a Chicago marketing firm to help us with our branding. They came recommended through a colleague. We were launching our brand to help Fortune 500 companies with their corporate reward programs. One of the pieces of our engagement was for them to create our logo for that market. We settled on an interlocking “C” and “R” surrounded by a circle of lettering that repeated “corporate rewards.”

A week after we had settled on that design, I was walking down the street in New York City. For all of us that are entrepreneurs, when you walk down the street, you rarely take in the scenery. You have a million things on your mind and rarely notice what is going on around you. I walked past a New York Health and Racquet Club with their logo and name on a large awning and happened to look at it. I was stopped in my tracks. The logo that our marketing firm had proposed was a carbon copy of the New York Health and Racquet Club logo, even down to the font.

The “C” and “R” that represented “Club” and “Racquet” were the “C” and “R” that represented “Corporate” and “Rewards.” No jury would have convicted me.

  • Who is CEO? We were attending a healthcare conference at Coronado Island off the coast of San Diego. Our booth at the trade show part of the event was across from a company that had an attractive woman in a doctor’s coat at their booth. It turned out to be their Chief Medical Officer. During the event, a few of our sales guys would flirt with her. As usual, I was running around talking to customers, prospects and potential partners and was rarely at our booth. Two nights later, I had finished dinner and walked to the bar and ordered a bourbon. The Chief Medical Officer was sitting at the bar with a colleague of hers that I happened to know. She mentioned she saw me across the aisle at the show at the IncentOne booth. She asked what I did for the company and I told her that I had founded it and was CEO. She said, “that’s strange, because one of your guys had come over to talk to me and told me he was founder and CEO.” After validating my credentials, I told her we should screw with my sales guy the next day and I would come over when they were talking and ask him what it was like to found a company.
  • What will you do for me? When we were about twenty people, we hired a developer to help us with internal systems. He could understand business concepts and quickly translate them into technology we needed. His job had him rolling out frequent enhancements to our internal systems. He interacted with our client services team that consisted of five women ages twenty-five to thirty-five. Every time he would deploy something, he would train them and when they thanked him he would say “I would do anything for you. What are you willing to do for me?” I guess this went on for several months before anyone brought it to my attention.

Accept it. Our teams are going to be dysfunctional—not the least of which is you.

I was driving to a meeting with ADP with one of our female sales reps and we were late. I’ve been known to put the pedal to the metal and we were buzzing through the streets of New Jersey trying to get to there on time. I was also talking on my phone. In the midst of casual conversation with her, she said “can you pull over for a second?” She opened the door, stuck her head out the window and threw up. She leaned back in the car with a look of horror on her face. This is when the ridiculousness of an entrepreneurial mind takes over. My first reaction should have been “Oh my god are you okay?” Can I get you something to drink?” I looked at her for two seconds and said “are you okay?” She said “I’ll be fine.” I slammed the car into drive and started speeding back towards ADP. We ran into the building and she went into the bathroom and collected herself. I remember thinking, “I wonder if we are going to blow this meeting because she smells like puke.” What I should have been thinking is that I should have planned better, left more time, been more sensitive to the person in my car and driven slower.

Despite our appreciation for their commitment and dedication, the people we consider our early stage team—whether they are employees, consultants, or vendors—may not have the skills or qualifications to advance our business. This is not to say that they can’t be effective members of the team. For us to remain sane, and not be frustrated every day, we must accept that the team is dysfunctional—it just happens to be our dysfunctional team. Try not to drive yourself, or them, crazy along the way.