1. Jessica Livingston
It'd be great to hear Jessica Livingston, author of Founders at Work, talk about her experiences at YCombinator. Most of the interviews / talks I've heard from her are about her book, which is very good, but I've heard it already! :-)
From what I understand, she provides some invaluable advice at YC, and it'd be great to hear her stories of those startups, and (in her position as a YC applicant interviewer), her thoughts on the larger startupper population.
2. Rand Fishkin
Founder / face of SEOMoz, everytime I've seen Rand talk about SEO, I've been impressed about how good of a communicator he is. I've read a few posts on their blog about SEOmoz as a startup, but it'd be great to hear his thoughts specifically on:
the journey to establishing your company as the authoritative service / voice in an industry.
how to deal with working in an industry that's a highly sought after service, valuable and legitimate when done right, but filled with charlatans and receiving a ton of bad / mixed press because of it.
running a company that's very dependent on companies higher in the food chain (search engines themselves, in their case). Dealing with sudden changes, getting accurate data, and trying to provide consumers with clear answers when the search engines above them are trying to keep the truth obfuscated.
3. Scott Kirnser
Not a startup founder, but a journalist that writes the Innovation Economy blog and a column for the Boston Globe. Scott has a significant platform of his own for his thoughts on startups, but he's usually either reviewing a specific startup, writing on the larger economic picture, or discussing venture capital.
It'd be interesting to have someone else asking the questions, and see what he has to say about successful startups, startup journalism, and how different cities are making different names for themselves within the startup world.