This is a good thing to wonder about. I know I spent far too much time wondering about it myself.
I think there are a number of possibilities...
* He didn't believe in the technology
* He didn't understand the technology or how/who to deploy it
* He didn't have the patience to walk the longer road to much greater $$
* His life was so expensive that it could only be supported by theft
* He learned his 'trade' (con-artistry) growing up from his brother and ??
* He has some form of mental illness
For my part, I think it might actually be some form of all the above.
In addition, many of the problems associated with the company were rooted in an overall lack of corporate strategy. Instead of focusing on things like a defined core customer base (should have been government, friendly governments and mega corps IMO) the company was acting more like a desperate teen right before prom. Any body would do as long as it provided a story (press release) that could be told. That lack of strategy translated into a number of other problems.
There was a lack of focus and direction within the engineering side of the company. Projects undertaken that never would have cleared an ROI hurdle. Allowing Al Carlson to 'research' whatever he felt like rather than focusing on the core needs... the biggest example being the decryptor that was never finished. Massive amounts of wasted time listening to Carlson pontificate about things that were irrelevant to the concept of actually putting out a product... something he has no concept of doing. Time spent managing the fragile ego of Carlson. Time spent trying to undo damage being done by Carlson (lies told on conference calls, preventing him from giving the source code away, etc). People on the payroll that never should have been there (i.e. related to MDLG and/or not qualified). Massive amounts of wasted time due to chasing every shiny object that came along. No funding for items needed to complete tasks (or even have toilet paper in the office). No sense of urgency to complete anything (other than press releases). The inability to hire good sales people (due to the insanely low commission MDLG was offering them). MDLG consistently spending little time in the office. Failed potential sales due to a lack of planning and lies about what the product would do (from both MDLG and Carlson). Finally, a general lack of professionalism.
If a person possessed any drive and ambition then working in such a setting would have been a daily nightmare... and it was. When you start to wonder if your place of work was built on an Indian burial ground and is thus cursed... it's a sign things aren't going well.
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