I agree with your first paragraph, but Adams has described how his Trump writing has decimated his ability to earn money as a public speaker because people who hire such speakers want to avoid controversy. Adams appearing on the podcast of an obscure college professor was an act of altruism.
So you think he assigns a lower probability to Trump winning than someone unfamiliar with his argument might suppose? In theory he might have lost more than 2mill * 0.38 = 760000, but the higher that probability goes the worse your argument sounds.
In the second half of the interview we discussed several topics of importance to the LW community including cryonics, unfriendly AI, and eliminating mosquitoes.
https://soundcloud.com/user-519115521/scott-adams-dilbert-interview