What boggles my mind is Game #2. On one hand, like Jared says, Kevin may have been in deep and still is. I get that. But we have all been there in our life. If you are in deep when you do not take on more. On the other hand maybe he thought he could handle it? This part really blows my mind when I ponder it. If everything was under control and customers happy (a high% I mean, you can never please everyone) then sure, you take on a new project so as to eliminate gaps in your business (peaks and valleys are costly and difficult for start ups). If things are not under control then the last thing you do is take on a new project and jeopardize the business as an entity with unacceptable risk!
Which is it here? I have no idea....what is implied is maybe he was on overload and did not own up to it and thought he could "Do it all". If true, a good Program or Project Manager could have prevented much of this and kept the customer base at ease. A Project Manager drives timelines, coordinates suppliers and associated cost, has good communication with the customer(s), maintains tight budget control while the "Exec's" are off doing what they need to do relative to their vision of the company.
What was missing in my opinion? Yes, a Project Manager from day! Kevin (being a techno type guy it seems) would be able to do what he needed to do while a home base Project Manager kept things in order.
My 2 cents