Awesome. Could you just make it a little worse? Thanks
The first thing that the finished logo made me think of was old book covers--http://ecx.images-amazon.com/images/I/81YS9egzy2L.jpg is an example (that I found after googling "book covers that 'Not That Kind of Girl' was mimicking.) I think the new one really (really, really) exaggerates the old-fashionedness of the big serif "Jeb" font, which makes a lot of sense with his being kind of a blast from the past. It still has the very modern "2016" but overall it looks much less modern and trendy than the designer's final draft. Given Jeb's target audience, I think that what they went with makes sense.
/not a designer