I would also highly recommend this book for a very bottom up and practical guide to getting things done. The author was doing bootstrapping single person IC design a (relatively) long time ago. Unfortunately, I don't think there's an easily accessible pdf online. https://www.amazon.com/ASIC-Design-Silicon-Sandbox-Mixed-Signal/dp/0071481613

thanks for the tip. Here is a PDF of the TOC: http://www.gbv.de/dms/ilmenau/toc/522470521.PDF