You may have to use different person’s. Although it was not stated for mandatory criteria and Optional criteria (1 & 2) , it was stated for OC 3 & 4 to use a different person other than the ones you used for letters of recommendation.
But I’ll strongly advise you to use different persons. Diversity of opinions from tech leaders makes your application stronger.
For the second question, I do not think it is compulsory that the founders must raise money. But I think raising significant cash gives further validation of your startup. You can use other evidences with metrics like: customer growth/acquisition, monthly active users, revenue, downloads, news clippings etc