The Pros: I had a good time with the CEO and all the players; I refined my understanding about what someone says and what he can and will do; I didn’t spend much time on it, and really had relegated it to “personal” time; it never interfered with my core workload; it wasn’t the first vapor-paper I’d ever received.

The Cons: But after many years of failing to produce the software, and regularly-changing key players; no consistent capital strategy; and the CEO’s persistent excitement about each new team, I gave up. It was clear no one actually understood the software development process, and that this was the CEO’s dream but not his primary focus.

Experience Two

I later spent a good deal of time with a small group of entertainment entrepreneurs who were beginning to build an online entertainment website portal. The market timing was appropriate (if they could move quickly); they had a good rolodex that might support the venture; they had enormous enthusiasm; they had a charismatic spokesperson; I liked all of the partners. I was restless at that time and wanted something more fun to work on. In the end (not very long after we began), I left the group when it became clear that not one of them would step up to the actual leadership of the venture, and essentially wanted me to assume that role.

The Pros: I had a good time with them while I helped them, and learned more about them. I enjoyed my time with them. I didn’t set any deal in place while I investigated what they could do, so there was nothing to “undo.”

The Cons: I spent far too much time with them while I was busy with paying clients, so I created more pressure for myself than I needed to. I was disappointed to see that none of them would assume a leadership position, which refined my perspective about entrepreneurs who dream by do not do. (this last part is a “pro.”)

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