You can see in Simons' TED interview with Chris Anderson how he gets rather annoyed with Chris at times, particularly when Chris mentions Simons' "amazing mind" at around 8:30. Simons seems, to me, to be a rather pragmatic and humble person who doesn't particularly enjoy flattery. Chris even throws out a quote by Musk at the very end of the interview, fishing for some similar platitude from Simons, but Simons deftly avoids giving out such an empty quote.
https://www.youtube.com/watch?v=U5kIdtMJGc8
Most interestingly, you can tell Simons' like of science and mathematics and alludes to his interest when he mentions his investment into the origins of life towards the end.
There are two interesting talks or interviews I know of with Simons:
* Full-length Numberphile interview: https://www.youtube.com/watch?v=QNznD9hMEh0
* His lecture on his life given at MIT: https://www.youtube.com/watch?v=SVdTF4_QrTM
Simons actually attributes a lot of his success to luck.