Nov 152014

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Dr. Earl R. Smith II


It had been some time since our last meeting. An e-mail showed up indicating that she was ready to sit down and talk. When we began the engagement neither of us was sure where things were going or where they might end up. Our last meeting – some weeks back – had started with some tension in the air. My coaching client had made a successful career as an entrepreneur. She sold her companies and made a lot of money. After a brief ‘vacation’ from business, she began to cast around for her ‘next life’. After some reflection she had decided to become an angel investor.

Although it seemed that she was made for the role – an experienced, successful entrepreneur with a fat bank account – things did not go as planned. She had been relatively successful running a number of companies – ones in which she had acted as either the CEO or Chairman. But her experience as an investor was different. Her first portfolio company was giving her problems.It had burned through two tranches of funding with little to show for it. Revenues were a small fraction of those projected and expenses had shown a tendency to exceed expectations. The company was running out of money and she and her fellow investors needed to decide whether to provide additional financial support or put the company our of business. I was asked to help them make that decision. But the engagement quickly turned to focus on her decision to become an angel.

The sea-change came after an initial meeting with the senior team of the problem company. The meeting took place at the company’s somewhat over-adequate headquarters. I was introduced as a senior adviser who was going to help the investors decide what to do. Some of the senior team was clearly anxious. Most had enjoyed the relatively open and unstructured culture of the company. The fact that it was losing money and about to run out of funding was, of course, a matter of concern. But this approach seemed a bit of an over-reaction to a couple of them. To her credit, the CEO stood her ground and insisted that this was the way forward. She expected every member of her team to support the process. In the end they agreed. But I made a mental note of those who I figured would not survive.

It did not take me long to complete my initial assessment. The postmortem that she and I conducted over drinks took a turn that resulted in the tension from our last meeting. It was painfully clear that, although she had been very focused on performance metrics as a CEO, she was much more lax in her approach and demands as an investor. The turn came when she admitted “I know why I have been acting this way,” she said. “My whole experience has been on the other side of the metrics and I have always gamed the system to maximize my and my team’s interests. Now, I am on the other side. Every metric that is met, cost me. So I have avoided metrics and the costs.

For the first time she began to appreciated the position of her prior investors and the role they had played in helping her succeed. She began to appreciate how their role differed from hers and how the two combined to make for success. But she was not her prior investors. Her decision was personal and would effect the way she lived the rest of her life. Things came into sharp relief when I suggested, “So you sabotaged your own interests to keep from being in opposition to the people who were playing the role you used to play.” I remember thinking as I left that meeting, “she has a big decision to make and it is not about what kind of investor she should be.”

Facing the Music

These situations occur frequently in my coaching engagements. There is a point that the client sometimes reaches when they simply have to go away alone for a while and think things through. We had reached that point. It was, as they say, ‘in the hands of the gods’. So, after weeks of silence, when I received an e-mail request for a meeting, I wasn’t sure what I was going to hear. She has selected one of my favorite watering holes; I had spend considerable time teaching the bartender to make martinis the way I like them. That was a good sign.

I always arrive a bit early for every meeting. It is a habit that has yielded many benefits. I get settled in, focus my mind on the coming session and get through the first couple of sips of a cold one. In this case, I chose a spot over in the corner. By the time she arrived, I had run through my settling in list. As she sat down, she pushed a box across the table. “This is for you“, she said, “go ahead, open it.” Inside was a sterling silver flask wrapped in a check for several months of engagement fees. As I unfolded and looked at the check, I noticed her smile. The flask was full of Whiskey. It only took me one sniff to identify Macallan 30. I smiled. “So what is all of this for“, I asked?

She settled back and smiled. “You have helped me on a journey that I never anticipated making. I thought that I had it all figured out after taking some time off from selling my last company. You know me – once I get the bit in my teeth, I am a woman possessed. When we started the engagement, I was certain that you would help me become a better angel investor. I had no idea that I would end up where I am.

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